II. Fall 1945-Spring 194


A college preparatory school for boys and girls

from the seventh through the twelfth grades.

Incorporated 1945 not for profit.

Board of Trustees
Owen Moon term expires 1949
Elizabeth F. Johnson term expires 1948
Lee Anderson term expires 1947
Evelyn Carter Giles (Mrs. Howard Giles) term expires 1946
David W. Bailey Vice-President of the Board
Kenneth B. Webb President of the Board
Ruth Schenk Hawkes (Mrs. R.S. Hawkes) Secretary of the Board 

David W. Bailey, Co-director
Elizabeth F. Johnson, Treasurer
Kenneth B. Webb, Co-director
Johanna S. Peterson, Secretary 

References by Permission 

Other Friends of the School

Professor Joseph Albers, Black Mountain College
Samuel Barber, Composer
Ward M. Canaday, Chairman, Willys-Overland Motors, Inc.
Dorothy Canfield Fisher, author
Bliss Forbush, Friends School of Baltimore, Md.
Anne Bosworth Greene, Author
Mr. and Mrs. Owen Lattimore, Baltimore, Md.
Mr. George Mullins, New York City, N.Y.
Mrs. Elliott Speer, The Masters School
Dr. Charles C. Tillinghast, Horace Mann School for Boys

[This first list of "Friends of the School" also included 32 names
of the parents and guardians of the first year's students.]  

Location and Physical Aspects

Woodstock, Vermont, elevation 700 feet, population 1,200, is on Route 4, 13 miles from White River Junction, 36 miles from Rutland.... There are five churches, three local doctors (with the modern Hanover Hospital 18 miles away) and three good inns.
The forty-acre tract of upland meadow and woodland which constitutes the main property of the School is situated about five minutes walk from the Green in Woodstock. On this land, besides the ski slopes, an outdoor swimming pool near the woods, pasture land and a garden area, there are two large buildings. One [Greenhithe] houses the girls’ dormitory, dining-room, infirmary quarters, office, faculty room, common room and -- at present -- all but one of the class rooms. The other building [The Barn], a roomy and picturesque barn, houses the science laboratory, a small gymnasium and theatre, a master’s suite, and beyond a heavy sliding door, the quarters for horses, cattle, and poultry.
The School owns another piece of property on the Green [The Green], a large old double double house with two beautiful fireplaces which are noted in Woodstock. This building is the boys’ dormitory and provides space also for resident faculty. 
                                  -- WCS Catalogue for 1946-47 (selections), December 1945

When the Woodstock Country School opened, on September 26, 1945, there were 35 students enrolled. There was a senior class of three, there were one or two juniors who were also war veterans, and, contrary to the catalogue, there was even a sixth grader. Some students had scholarships, but most were paying the full $1,200 a year fee for tuition and board (day students, $300). Most of them came from the Atlantic coast region, from Arlington, Virginia, to Maine. Several came from New York City, several others from Boston. They all came to this new and unknown school through networks of relatives, friends, and colleagues that Ken Webb, David Bailey, and Elizabeth Johnson had developed over the years. These contacts delivered a diverse group. The first student on campus arrived well before the start of school, because she had nowhere else to go: Patience Malet, an English girl with her own horse, whose mother was an Army lieutenant in Denver. The three seniors were Phebe Brown of an old Boston family, Ray Carpenter who was heading toward a military career, and Mary Lea Johnson of the Johnson & Johnson Company family (she came from an unhappy time at the Dobbs School, recommended to Woodstock by friends of Miss Johnson). Roger Phillips chose Woodstock because there was no formal dress code. Louis Wislocki, unhappy at Milton, found his way to Woodstock because his mother, Florence Clothier Wislocki, had been at Baldwin under Miss Johnson (who soon drew her into working on the school’s behalf). Dr. Wislocki, who was by then a child psychiatrist on staff at the Home for Little Wanderers in Massachusetts, recommended one of her youngsters for the school: Jimmy Barter from Maine, remarkably bright, but with a Dickensian childhood that led to serious trouble with the law by the time he was 13. He agreed to accept a scholarship to Woodstock because its mattresses were better than the ones at reform school. Harvey Tyler became the school's youngest student, a sixth grader, because his and David Bailey's families were old friends. Joe Bernhardt's father was in the U.S. Dept. of Agriculture in Washington. David Ezekiel's father was an agriculture specialist for the United Nations. Klaus Heimann, who fled Nazi Germany with his family in 1939, was having a terrible time in public school in Massachusetts until a friend of Miss Johnson arranged for him to have a scholarship to Woodstock. Mary Lou Doggett and Lillian Russell both came over from the Farm and Wilderness Camps, as did Ken Webb’s daughter Susan (Sukie) and his seventh grade son Robbie. Helle Krafft came from Norway as a ninth grader, happy to get away from five confined years of war and her mother. Walter Walker's aunt, Helen Gahagan Douglas, knew the Baileys through spending summers in Vermont. And so it went. Whatever brought them to Woodstock, any students who thought about it certainly knew that their 35 places there were not won through fierce competition (there was not even an entrance exam then). But for most, that was just the first of the school's pluses, offering a cooperative respite from bruising competition. Even more important in 1945 was the newness, the sense of adventure, and the growing belief that they were creating something of lasting importance, a school with humane values.
From the beginning, Woodstock was a place where a student could get another chance, socially, academically, emotionally. At Woodstock a student's past didn't follow him or her as relentlessly as it surely would at other institutions. Instead of the ruthless, destructive competition of schools which created at least as many losers as winners, Woodstock's cooperative communal philosophy meant that the school tried to meet the needs of every student, regardless of how gifted that student might or might not be. Woodstock offered a refuge to all kinds of students, a place away from the "real" world or the "natural" family, at least for a time; a place where one could define oneself as one might -- and maybe even be accepted for that. The school welcomed idiosyncracy gladly, encouraged considerable experiment, and expected hard work, both physical and academic. At the same time the school expected students to progress, to mature in fairly traditional ways, and while it put up with those who tested the limits of acceptable performance for a long time (some thought too long too often), it did not tolerate them forever. The inherent tension between these sometimes contradictory goals -- providing sufficient relaxation to encourage emotional growth and, simultaneously, setting very high standards -- gave the school its special dynamic. Not all of Woodstock's students were kids seeking refuge from one storm or another. Some were attracted by the sheer vitality of the place. When the school worked best over the years, it also had a solid minority of students who most wanted an academically strong school that would provide the intellectual challenges that they weren’t getting where they were.


"It was an absolute lifesaver. I was there the first day of the school which was in '45. The very first day. And I graduated in '49. I came out of a family that had -- my father had been in the Second World War and, you know, he enlisted. He was old at the time, he had a First World War record. He enlisted in the Second World War thinking it was going to be over in six months, and it wasn't.
“It went on for four years. It really drained the family resources in more ways than one and home was not a great place for me at that time, and I wasn't reacting well in public school either. I don't know why, I think it had something to do with the fact that my father did go to war. It was just like losing a parent. You go crazy. I became kind of a delinquent. And then when I got to Woodstock, it was like finding a new family."
-- Roger Phillips '49, interview, May 17, 1984

"I went because my father was starting the school. He believed in a truly academic education and, I think, had very creative ideas about education, very creative ideas which were grounded in a solid academic training, and it was the most obvious thing in the world for his children, then, to go to the school that he was heading....
“I was in eighth grade, and it was a small faculty, obviously, so I had my parents from time to time as teachers, and I remember my father teaching a course called ‘Modern Language,' which explored oral techniques we take so much for granted these days.... I was a day student, but we were living in the boys’ dorm down on the Green…
“I don't remember the first day. I remember that first year we had World War II veterans.... I had just turned 12, and to have somebody who had been in the war,... and very such older, I suspect he was 19 or 20. It seemed a lot at the time.... We were a fairly small group, we knew each other well. There was a sense of informality, a nice feel of informality, not informality to the point of sloppiness... Actually, the academic training I got at the Country School was really terrific, and I then sort of glided through my senior year at the George School, and certainly had no problem making the transition to college."
-- Susan (Sukie) Webb Hammond '50, Interview, April 30, 1986

"I loved the school also, I came from Norway where we just had had a 5 year long war. It was rather fantastic to be able to buy and eat as many bananas and oranges and any other things you wanted. It was also nice to get away and to be by myself, I really grew up the one school year I spent there.... I didn't know the language at all when I came to the school (I could say yes and no when I arrived), but everyone was very helpful and very eager to teach me English, so I learnt fast.... My writing didn't come as easy as my speaking, so David suggested I write a diary and he would correct. That worked beautifully.
“...about David and Mr. Webb -- that's the way we addressed them, and that should tell you something about them.... I remember David was very rude to me once and made me cry for what he said, and [a senior]Phebe Brown I think it was told me not to mind, that was just his way now and then. He took most interest in the elder kids, but usually he was nice, but a bit aloof. I liked him very much,"
-- Helle Krafft Sorlie '49, Letters, 1983-84

"I thought it was a school that was made up of misfits and people who had been thrown out of every prestigious boarding school along the East Coast. I'm not sure if that is actually true, but there was certainly that feeling about it. I was very unsophisticated when I came to the school, I was very much in awe of the kids, – I mean everybody there had a background -- adopted daughter of a famous psychologist, nephew of a liberal politician, children of government officials -- everybody had some kind of distinguished background.
“But one was a dirty boy, there was no other way of describing him. He rarely changed his clothes, he'd wear his pants until they were stiff and dirty, he slept in his engineer boots -- I remember him sleeping in his sheets and not changing them until they got black. He was just dirty. And I was this kid from a shack in the woods of Maine, or not very far from it, I had no claims to sophistication, but I mean, he never showered! We didn't even have indoor plumbing where I grew up. We had an outhouse, and bathed once or twice a month in a tub in front of the kitchen stove, where the water had been boiled to make a bath, so I wasn't the most fastidious kid in the world. But that one really was in a class by himself."
-- Jim Barter '48, interview,

In the midst of it all were Ken Webb and David Bailey, trying to work together to make sense of the variety of backgrounds, needs, and expectations all tugging the school in different directions. At the same time they were trying to make sense of each other as well, to make their marriage work, as it were -- but it made for an odd family to have two father figures and no true mother figure that first year. But most of the children were accustomed to odd families, and this one had all those additional faculty aunts and uncles to help out (most of the time), so the school worked at least as well as some families and better than others.
With two degrees from Harvard, Ken Webb was the most impressively credentialed member of the faculty, though several other teachers also had master's degrees. In addition to being the dorm head at The Green, Ken taught senior and junior English, Latin and Greek, and a course in General Language for eighth graders. He also wrote the school catalogue and general publicity, and supervised the student magazine, Symposium. His wife Susan was a part-time teacher of Latin and Greek, and of necessity helped run the dormitory, where they lived with their three children (two of whom were day students). In the dorm, the Webbs invited the students in for snacks every night.
In contrast to Ken, David Bailey was always a little diffident about his academic achievements, in part no doubt because they were not remarkable, but also because he held other values, such as "good citizenship," at least as high as academic success. David had attended Harvard, with mixed results, before transferring to Black Mountain College the year it opened. His two years at Black Mountain, from which he took his degree in 1935, were a transforming experience for him, full of energy, vitality, and hope which he wanted to recapture in different ways with the Country School. David taught Social Studies and English in the lower grades, as well as organizing athletics and social events ("Ken didn't think much of me as an educator, so I was put in charge of recreation," David said years later). His wife Peggy was a part-time English and drama teacher, whose involvement was limited by a serious illness for which she was hospitalized that summer. She and David lived with their son Peter some distance from the school, in a house where Peggy felt isolated and alone, in part because "David was completely immersed. When school began, the school just drew him into it, and he became completely immersed in new faculty, new students, and just keeping the school's head above water."
To instruct their disparate student body, and to meet their sometimes greater non-academic needs, the co-directors hired a faculty of five full-time teachers, another six part-time teachers, and a non-teaching staff of four (a secretary, a cook, a nurse, and a maintenance man). The faculty and staff filled out a school family that included not only the "children" spread over seven or eight chronological and many more emotional years, but the "parents" who covered three generations. The youthfully ubiquitous Elizabeth Johnson (she even became treasurer of the student magazine) was old enough at 64 to be the grandmother of the 22 year old art teacher who looked no older than some of her students.

Edith Cochran
Edith Cochran not only taught math at all levels, she was in charge of the girls dorm in Greenhithe, where she frequently held afternoon tea parties for selected student guests ("a real aristocrat," David called her). She came to Woodstock with 20 years teaching experience and became one of the school's dominant personalities during its first six years. She had a graduate degree in Landscape Architecture and took care of much of the school's landscaping for the next few years. She had taught landscape architecture at Smith College for years, then taught at the all girls school, St. Mary's in the Mountains (which was then a very strict, traditional place, but has since turned itself into the coeducational White Mountain School, with very much of a Woodstock appearance if not the progressive substance). David recalled "Edith Cochran's innovative course in geometry -she used no textbook but instead required the pupils to create a theorem book of their own slowly and logically. More than one non-math student was successful in getting through the course and thus receiving a diploma."

Bob Lake
Although Bob Lake was one of the younger faculty, he, too, was one of the school's first defining personalities. He was a veteran of the Tenth Mountain Division, the ski troops, though he had never seen combat. Ken Webb had hired him to work at the Farm and Wilderness Camps the year before the school started, then hired him again as the first member of the Woodstock faculty. A Dartmouth College graduate, Bob had three years experience teaching at other progressive schools and had worked for the Vermont Soil Conservation Service. He taught Biology, Zoology, and Farming, and lived with his wife and three children in the former groom's apartment in The Barn, the classroom building near Greenhithe. This made him generally available to students, whom he enjoyed immensely, which contributed to his becoming the central figure in a major crisis several years later.

Faith Murray
Faith Murray, who taught art, was young and single and lived in Greenhithe, where she was Edith's assistant in running the dorm. Diminutive but dynamic, Faith worked with every student in the school, whether the student wanted to draw or paint or sculpt, or not. Busy as she was, Vermont was too remote for her and she left after a year. (David had recruited her from Black Mountain, where she had studied with Josef Albers, and he turned to Albers several times over the years for art teachers.)

Bert Sarason
Another one-year teacher was Bert Sarason. David hired him over the summer to teach Social Studies and English. He came to Woodstock after teaching in more rigid, impersonal places like the Harvey School (all boys, grades 4-8). A feisty New Yorker unafraid of speaking his mind, Bert was not always diplomatic about doing so. His students enjoyed his lively classes, including numerous digressions into school issues, even to open criticism of the codirectors.

Alice Bianchi
Alice Bianchi, wife of a Woodstock merchant, taught French (her native tongue) and Spanish. Discovered and hired by David over the summer, she came to the Country School with 16 years of teaching experience at Dana Hall, National Park Seminary, and Central High School in Washington, D.C. Although she taught at Woodstock for three years, she remained relatively uninvolved in the community.
The parttime teachers, in addition to the co-directors' wives, included Sue Beatty for music, Ted Gregg for religion, John Long for shop, and Carl Voss for social studies -- none of whom remained at the school after the first year.

Johanna Pederson
Although she was not a teacher until the second year of the school, Johanna Pederson contributed to the character of the place from the start, as the school's first secretary. She was the first of many secretaries in the school's history who served as an unofficial counselor, confessor, and cheerleader for all kinds of students.

In addition to the personal enthusiasm most of the adults brought to the enterprise, Woodstock opened at a time of remarkable confluence of other energies. In the post-war world at large, there was a profound surge of hope and idealism that the world would become a better, more decent place. The idea of the school was a part of the greater optimism that more humane institutions could create more humane people and a more humane world, an optimism affecting students and faculty alike. The freshness of the freedom the school allowed its students added an exuberance to the usual restlessness of adolescents busy finding out who they were, exploring the larger world around them, testing their own limits, falling in love, falling out of love, and generally feeling passionate about life in all its grand and trivial disguises. Focussing and intensifying both the global and the personal energies was the inherent dynamic of an institution being born.
For the most part, teachers and students alike threw themselves wholeheartedly into the task of creating their school, a task made much more fascinating and complex by the majority view that Woodstock should be a place which each new school generation could re-create for itself, to meet its own needs and perpetuate the energy of creation. Some even felt more strongly: believing not that the school could re-create itself, but that it should have to re-create itself constantly if it were to retain the vitality it needed to contribute to profoundly changing American education. Others, while wishing the school to be a shining example, also wished it to have a clear and more or less fixed definition. This philosophical tension, while always present, was rarely discussed directly, any more than fish discuss water. But because the tension was there, other, apparently less important questions generated emotional debate out of proportion to the importance of the nominal issue. In one such battle, the community decided that it would be all right for the soccer team to have red and white uniforms, but only on the clear understanding that these were not the school colors, that it was not right for the group to choose school colors at all because that would bind future students to a choice in which they had no say.
While a school could survive quite nicely without having official colors, other issues required deciding on a more or less permanent basis -- though deciding which issues should be decided could spark a lively discussion as well. Throughout that first fall term, throughout the first several years, the school hummed along on this vitality of shared new experience, the momentum of continual newness, the excitement of creating and controlling at least some of the terms of one's own life.
Academically, too, the school was full of ferment, with teachers pushing students to their intellectual limits in rigorous courses. Susan Webb recalled that "there was a great deal of challenge in the teaching,... [and there was] the feeling of the school, that the students and all, and the faculty, were very supportive of each other. It was the first school some of these kids had ever hit where there was some sense of freedom to learn and not to be stifled by just sitting in a classroom and that kind of thing."


"The first day at the school, it was a beautiful day in September. There was no precedent, so no one knew what to do. We were all kind of milling around in front of Greenhithe, talking and sitting on the steps and this and that, and somehow we all gravitated -there were thirty kids, approximately, pretty near the whole school that first year -- we gravitated to the hayloft in the barn. We were kind of exploring the buildings. But when we got to the hayloft we had a huge fight with the hay and jumping down off the rafters and, you knows piling on top of each other, and that was the lubricant that got everybody going, that was the sounding of the gong. From then on everybody was kind of loose, and the thing really started. There was a huge amount of camaraderie in the first year because we all felt that we were sharing that experience….
"My room assignment was in the dormitory down on the Green, across from the Town Hall .... I go up to the room, I'm rooming with some guy named Larry Hagman, and my sister and mother who were chatting as we went up the stairs, all of a sudden they're dead silent. I look back at them and they're staring at this woman I'd just passed, who was on her hands and knees on the floor -- this flaming redhead -- planing a bureau drawer. And that was Mary Martin."
-- Roger Phillips ‘49, interview, May 17, 1984

Already a long way from her roots in Weatherford, Texas, with a string of Broadway and movie hits to her credit, Mary Martin acted like just another 31 year old mother of a ninth grader when she came to Woodstock. On a visit in the following spring, she gave an outdoor concert for the whole school on the hillside above Greenhithe. Accompanied by her guitarist, she sang a wonderful variety of songs, including a rousing version of "Lullaby of Broadway." But such was the informality of the occasion that after awhile the students called for Larry to sing, too, so mother and son did a popular folk song together, after which Mary Martin said, "Larry, you have a beautiful voice. I had no idea."
Larry Hagman, the future J.R. Ewing in the 'Dallas" series on CBS, had learned of Woodstock through his step-grandmother who was a friend of one of David Bailey's cousins. "He was 14 at the time or something," David said years later, "and I didn't realize what a terribly naughty boy he was at the time, but he was a very naughty boy." Larry quickly became one of the stars of sorts in the school, where his willingness to try almost anything also led to his eventual forced departure. Larry is also widely remembered for his good natured, though sometimes extreme antics. Day student Margaret Nichols came to school by horse every day and, without asking, Larry would sometimes ride her horse around the baseball field trying to get it to perform rodeo tricks. Another time, perhaps apocryphally, Larry was on skis making love to a young lady, also on skis, when they began to slide out of the woods toward the lift line, so fell down on purpose, and told all their friends about it later. And Larry kept a striking photo of his mother on his bureau. One of his roommates, Jim Barter, who would become a nationally prominent psychiatrist, recalled coming into his room on the first day of school: "There was this show girl in a very skimpy costume on the mirror and I looked at it and made some sexist gross remark.... And Larry said to me, that's my mother. I was rather backward, I'd never known anyone's mother ran around looking like that. But I don't think he was peeved, I think he was just setting me straight. It was an interesting picture for a kid to have of his mother."
Both these boys came from broken homes. Larry's father was still back in Texas, his mother was remarried, and Larry had become an unruly kid who was always getting in trouble, until the Country School recognized the charm in his excesses. Jim's father had simply disappeared. Jim had taken his last name from the stepfather who'd been kind to him, but had died. He had nine half-siblings and another stepfather who beat him, and he'd spent most of the previous two years in jail or corrective institutions. In contrast to Larry, he no longer courted trouble, but preferred lying low ("I tried to blend in with the wallpaper"), to the point of hiding in the closet one night when his roommates decided to drink. The fourth roommate, also from a broken family, was Walter Walker, a talented artist and, contradictorily, a big, combative kid unafraid of any situation, who won David Bailey's gratitude more than once by keeping marauding townies at bay. These three, together with Roger Phillips whose family was still together but unhinged, reflect the kinds of needs and desires that filled the school with energy and ferment from the opening day.
The physical campus, focussed as it was on Greenhithe, heightened the sense of shared experience, common enterprise, community. All the boarding girls lived there, as well as two teachers. Everyone ate three meals there every day, as well as morning snacks and afternoon tea, all of which were served and cleaned up by the students. Some of the classes were in Greenhithe, as were most committee meetings and all school meetings where the community debated and decided how best to express its institutional values. Most of all, Greenhithe was the school's social center, not just for dances and other Saturday night entertainments, but for all those in-between moments and hanging out which let young lives take their own forms.
The powerful sense of community that suffused school life fills the pages of Symposium, which began as a mimeographed, student-run publication of universal purpose: "Our columns are open to members of the faculty as well as persons outside the school." [Symposium I/2] The March 1946 Symposium carried this brief, lead editorial: "This issue of the school magazine is somewhat different in that we have been able to afford to have it printed. Subscriptions remain the sole source of income as heretofore. Without endowment, and independent of the faculty, the Symposium is run by the students, and the articles and poems included in it are printed without censorship. For this privilege we are indebted to co-directors Mr. Kenneth Webb and Mr. David Bailey." [Symposium I/3]
The earliest Symposiums offer a kind of literate, collective family album, reflecting the eclectic intellectual life of the school according to the taste of its continually changing editors. While including some of the usual precocious poetry and fiction of bright high school magazines, Symposium also included articles about the school, the town of Woodstock, and the world, as well as reviews of plays, concerts, and other cultural events. One report on the school listed the 103 books (79 titles) read by 22 students in the 8th through 12th grade English classes during the fall term, adding that, "The average number of books perused in this period is almost five per person. Some students, of course, read less than this average figure -- but in no case less than three. Pat Malet, Walter Walker, and James Barter devoured eight, twelve, and fourteen volumes respectively." [SYMP I/2]
Some of the non-school subjects that students chose to write about were the peacetime military draft, the Civil War battle at Chancellorsville, the Trusteeship System and the Mandate System, figure skating, the Lost Continent of Atlantis, Richard Wright's “Native Son,” and deceptive political messages in comic books.
Among faculty, Ken Webb contributed an article answering the question “What Is a Friends' Meeting?”, Bob Lake wrote about building the school's new ski tow, and Faith Murray described some student art work. In particular she mentioned Walter Walker's explanation of a strange recent painting: "One late afternoon a friend of mine who was then quite young went walking in a graveyard. She wanted to see if there were any skeletons about. Suddenly she heard a mourning dove and it frightened her. I wanted to paint the way the mourning dove made her feel." As well as the generally much more playful and familiar work (landscapes, a dream of Indians, sculpted animals, a self-portrait, and a Madonna and Child), the art teacher wrote about a student who had fled with his family from Nazi Germany, "During this past month Klaus Heimann has produced two pictures well worth mentioning -- one of a very tough-looking helmeted God of War blowing an atomic bomb through a pea-shooter at the world, which hangs from a lamp-post; the other, just as dramatic, is of a bearded criminal being questioned under the strong yellow beam of a spot-light." (Klaus Heiman also wrote a bitterly wry piece about the use of surplus war material. Among his suggestions: "Bayonets would make fine can-openers and they might be used by the enraged wife on her spouse." [Symposium 1/21])
Woodstock's first term ended with the school's first dramatic production, a short Nativity play put on in the back of the Barn, where a few students kept their horses and the school had some livestock, including a cow. Peggy Bailey wrote the script and directed it, Larry Hagman sang a Christmas carol and, with great serendipity, the cow lowed at the end as if on cue.


Dear Santa,
if you don't come down the chimney this Christmas, we'll understand.
There are others whose needs are greater than oars ‑‑ Senators Bilbo and Wheeler, for example.
We know that your time is limited ‑‑ just a day's time; and there are always a few persons who require special consideration. But if you have a chance, won't you look in on Java, India, China, Greece, Middle Europe, and certain South American so‑called republics.
And if you have a moment to spare, won't you look in on our Oakies, our share‑croppers, our unemployed veterans, our Jews distasteful to Mr. Coughlin, and our negroes.
We hope you can make it now in December 1945, for, to tell you the truth, a lot of people in this world are losing faith in Santa Claus.
‑‑ Mary Lea Johnson '46, Phebe Brown '46, Jim Barter '48, editors, Symposium, Vol. I, No. 2, December 16, 1945

Woodstock has always looked with disfavor on the multiplication of rules, preferring to rely on the natural good sense and cooperativeness of boys and girls. Most of the procedure herein outlined should be regarded as the smoothest way, in the mature consideration of a number of people who have worked on the matter, to achieve that gracious and cooperative living with which our close‑knit community can be truly happy ....
Loss of privileges, penalties, punishments, etc. Smoking in or about the dormitories, except as it may be permitted by faculty members in their own rooms, constitutes a fire hazard which cannot be tolerated and will make a student liable to expulsion. Breaking the smoking rules in any other way will mean loss of the privilege for a definite time. Having in one's possession or drinking any intoxicating beverage anywhere in Woodstock will make a student subject to expulsion. Both of these misdemeanors are adjudged by the Discipline Committee. These rules regarding tobacco and intoxicants hold whether School is in session or not. Lateness in getting to the dormitory in the evening, lateness to bed or talking after 'taps' will mean no snacks. Lateness to class or other school appointments, or coming to the table with dirty face or hands, will mean making up at a special Saturday afternoon study hall double the time lost in the tardiness or in washing up for the meal in question.
Messiness in the dormitory will lead to an assignment of scrubbing the cellar stairs, the porch floor, or the brickwork of the fireplaces. Coming to the table with unsuitable or untidy dress will mean being sent away to change and the time thus lost made up in Saturday study hall. Going downtown with unsuitable or untidy dress will mean deprivation of the downtown privilege.
Clothing, books, or other possessions left around the building will be collected for the pound and redeemable for ten cents an article. Borrowing of others' books, clothing or other possessions without express permission of the owner will be treated as stealing and dealt with by the discipline committee (comprising the co‑directors and two other teachers).
‑‑ Ken Webb, WCS 1946‑47 Handbook, Summer 1946

Ken Webb wrote the first and only WCS Handbook to help new students get to know the school in the fall of 1946, and to remind old students of the rules and customs that had been established during the first year. The moral accountant style of this summary was never the actual style of life in the school. Nevertheless, the moral accountability implicit in the handbook remained part of the school's code for all but the last few years of its existence. The difference in this emphasis derived from the different styles of the co‑directors. As Ken defined their relationship in the handbook: "The school is set up under a system of shared responsibility, David Bailey or Kenneth Webb being responsible for its entire administration except for the financial control, for which Standish Deake [see Chapter 3] as business manager and comptroller is responsible directly to the Board of Trustees .... In general, David Bailey is responsible for students' individual problems, their daily program including sports and studies; Kenneth Webb for the curriculum, including study hours, etc., for the work program, entertainment, lecture and conference program, 'public relations,' and for all publications of the school, including this handbook."
In handling "students' individual problems," David increasingly shaped the school's character, adopting a much more flexible approach to the rules than the Handbook suggests. Certainly smoking in the dorms and drinking were always unacceptable, and students were even expelled for repeated offenses. But infractions like lateness were increasingly dealt with by those who were affected directly (classroom teachers or work crew supervisors, for example); or as they emerged as part of a problem pattern in a student's behavior. Likewise, the contradiction of using study hail as a punishment was dropped, although strictly supervised study halls were used to deal with students who had poor study habits or who tended to disturb others in unsupervised study. In other words, the school was a more relaxed place than the Handbook portrays not because of any great loosening of standards, but because of a loosening of the means of achieving or enforcing those standards. David took the students for who they were, adolescents who were bound to make mistakes. But he believed they needed the freedom to make mistakes if they were to learn from them. And he trusted most of his students would learn enough from their little mistakes to keep from making great ones. But he could, and did, deal harshly with those who pushed the limits too hard (as he eventually expelled Larry Hagman for one offense too many). But for most of the students, the school's freedom was more intimidating than enticing, and the system worked ‑‑ or at least taught students, as they matured, that they could misbehave more or less at will so long as they were discreet. (As David's style came to dominate the school, its Bulletin of In‑Formation a few years later had no section devoted to rules, although the rules regarding smoking, automobiles, pets, and firearms appear separately at logical points in the text. There is no mention of study hall or other minor rules.)
"David's way of controlling was different from Ken's,” recalled Gerry Freund '48, David's friend and admirer for 35 years. "David's way of controlling provided a tent within which you could operate with a lot of freedom. Ken Webb's authoritarianism applied to every single piece of your behavior. But David changed during the course of the years of his headmastership and there was no consistency. There were times when David would tolerate, and then there were times when David would excise students, sometimes in groups, simply deciding that they weren't for this experience. Nevertheless he infected his students. He gave freedom. He was capricious. He was the arbiter of this school. It was a one person school. There was never a possibility of anyone's competing for the center of attention. If they did, they would leave."
Perhaps the greatest expression of freedom during the first year of the school was that the students had some say in what the rules would be, and much more of a role in deciding how they would be enforced. Years later, David described the results: "It was James Barter who with us adults helped to organize the first student government arrangement, the student council which we thereafter felt was the most important element in all the years that we ran the school [until 1967]. Right from the start we set up a student council so that it directly represented their electorate. Each academic grade elected a representative and each dormitory elected one or more representatives, depending on the size of the dorm. This system prevailed for over 20 years. The student government system was not unique with us, but was indicative of the fact that our school was student oriented, that its government was jointly run by the whole school population, with great respect for each individual and that the adults were superior only in academic attainments."
The student council's responsibilities varied over the years, but they generally included such jobs as running the dorms, supervising study halls, and serving as the ODA, the OD's assistant. (Each day a different faculty member was designated as OD, "officer of the day" in charge of running the school, responsible for making sure students came to chapel and meals, attended classes and study hails, and signed out for afternoon and evening activities ‑‑ or accounting those who were missing. Much of this was delegated to the ODA, along with running errands, greeting visitors, and answering the school phone after the secretary went home.) In addition to this sort of helping to paint Tom Sawyer's fence, student council members were also expected to report any students they saw breaking rules, an expectation more honored in the breach than the observance by most students. The council was also called on to sit in judgment on its fellow students, and even its own members, when deciding who should get special privileges. Council meetings almost always included a faculty advisor (usually David), and final judgment on council decisions was reserved to the faculty or co‑directors. The inherent contradiction in this arrangement (the shared illusion of student power without its substance) would begin to undermine the school in the early 1960s, when students openly expressed their eternal reluctance "to be policemen." After several re‑organizations aimed at maintaining some sort of student government, the whole idea vanished in the late 1960s, by which time it was the faculty that was openly stating its reluctance "to be policemen” with no coherent central authority remaining to suggest that maybe that was part of a faculty member’s job.
During the first years of the school, the student council's functions were not yet fully defined, as Ken noted in the Handbook, adding that "it is part of Woodstock's purpose to give students as much practice as possible in setting up and administering their own democratic government, to turn over an increasing proportion of student activities to their control. The Student Council should not become merely a police force, but should continually be creative in its administration of student affairs." The student council was not created to be a legislative body, although it was encouraged to petition the faculty with its proposals. But even the faculty's legislative authority was sometimes ambiguous. Insofar as the school had a democratic decisionmaking process, it included the whole community acting in the forum of the weekly school meetings, of which the student council president was the moderator. This arrangement provided the students with some real power over their lives when the institution was new, and for most of the school’s life in modified forms..

Any new institution struggles to make its reality live up to its ideals. Woodstock's struggle shows up in the school's first formal catalogue, written by Ken Webb with remarkable frankness after only one term of Woodstock life. The 16‑page pamphlet systematically reviewed the school's goals and achievements in "Scholarship," "Athletics," "Religion," "Esthetics," "Democracy," arid "Work." Ken explored each of these under two headings, In Theory and In Fact:

In Theory, Woodstock's ideal of Scholarship put a higher emphasis on intellectual integrity than was encouraged by more traditional schools (or the culture at large, one might add): "The school should stimulate intellectual curiosity, should create an interest in good reading, good discussion, in clear, independent thinking, and a desire to continue self‑education.. It must establish habits of sound scholarship, sure mastery of fundamental skills, and must keep in sight the objective of adequate preparation for college."
In Fact, Ken reported, "All the students do not study all the time, and not all assignments are satisfactorily prepared, but the gratifying amount of serious study which is being put into mastery of 'tool subjects' is done with an understanding and a willingness which imply that classes are stimulating. Students have read far beyond the requirements of courses. They have responded eagerly to informal talks and discussions by well informed guests on a variety of subjects. The writing in the two issues already out of the quarterly mimeographed 'Symposium' shows a surprising breadth of interest, not only in things of the mind, but in the affairs of the world in general. If pupils have not all achieved intellectual curiosity in full measure, they have, as a whole, gained a remarkable degree of awareness of the immediate and the wider community of which they are a part." For most of its first 30 years, Woodstock rightly prided itself on its high academic standards, as it consistently sent its best graduates to the best colleges. But when the school ran into difficulty, declining academic rigor and achievement were among the clearest signs of other, deeper problems.

In Theory, Athletics at Woodstock included regular vigorous outdoor exercise, activity that benefits every muscle and helps to develop a sound body, sports and games played for the joy of playing, team play in which one puts forth all he's got with no thought of self, the building of wholesome attitudes which lead one to value health and physical fitness." In Fact, Ken reported, "Just the work of settling in during the fall term has provided much of our regular physical activity. There have been frequent 'pickup' games, no formal athletics." Eventually Woodstock would play other schools in soccer, field hockey, ice hockey, basketball, and tennis, which replaced baseball in the early 1970s. Woodstock teams usually lost, and a .500 season was a rare accomplishment.. There were occasional moments of glory like the 1950 baseball game in which Dave Pope pitched the school's only no‑hitter, but sports never became the focus of the school. With most teams having more positions to fill than good players to fill them, athletics remained a source of cooperation much more than competition.

In Theory, Religion was to be integral to Woodstock life: "Spiritually, the atmosphere of the school should be definite and vigorous enough to lead students to the conviction that the principles of Christianity are vital, that they afford a satisfying way of life, and that religion can be both a source of strength and a transforming force in individual lives and in society." In Fact, Ken noted, "The attitude of students here in worship services, though often impatient of the formalism of traditional ritualistic worship, is not only serious but reverent. Visitors who have attended occasional Sunday vespers or daily chapel, both types of service conducted by the students, have commented on their feeling and sincerity." The brief morning chapel was usually non‑denominational if not non‑religious, led by faculty, students, or visitors who sometimes sang hymns and prayed, and other times played jazz, read poetry, or talked about public issues. Vespers was likely to be more traditionally Protestant, as when Elizabeth Johnson gave her sermon titled "Get Thee Behind Me Satan," but it could also take the form of a Quaker meeting or a discussion of military conscription. However, no religion, not even Ken's Ouakerism, ever became a focus for the school. Like sports, religion remained more an opportunity for communal cooperation than doctrinal competition.

In Theory, with Esthetics, "We would have students gain here a sensitivity to beauty and a realization that everyone has some modicum of ability which can lead to satisfaction in art and music. Everyone should do enough painting and drawing and sculpture to appreciate good art; everyone should know the joy of an hour around the piano singing.” In Fact, Ken wrote, "Every student has had the experience of drawing and painting, some of the boys most unwillingly at first, but later with an interest which has broken down barriers of diffidence, self‑consciousness, and belief that such pursuits are 'sissy.'" Art and music, and later Drama, would continue to provide esthetic focus for the school for most of its life.

In Theory, Woodstock was a strong proponent of Democracy: "Education to be fully rounded must include training in cooperation and democratic living, in the realization that each individual has responsibilities toward the community as a whole. Students should have the experience of governing themselves in the many areas where this is possible." In Fact, Ken acknowledged, "we see many small failures in cooperation, in democratic procedure, yet necessary work gets done, someone is always ready to help ‑ when help is needed; and students are actually learning what democracy is, how it can be properly used, even what its diseases are, such as indifference, pressure groups, unawareness of the demagogue." Democratic processes and decision‑making, and their implicit power struggles, would be an increasingly important part of the school for most of its history.

In Theory, the school saw great value in Work: "Estudents] should have the opportunity to do most of the work necessary to the daily life of the community. To strengthen and broaden this work experience, there should be a farm to teach responsibility, respect for work, and appreciation of the labor involved in the production of so many things we take for granted." In Fact, Ken wrote, "The farm is full of plans, not achievement, at present. We have been able to give students opportunity for realistic work, even in caring for a cow, 3 goats, 4 horses, and a miscellaneous assortment of calves, turkeys, chickens, and pigs. This spring a large garden, mainly of fall crops, will be planted, and by next autumn, with somewhat more stock, we should begin to have a truly productive farm unit."

Woodstock's farm operation would never become an integral part of the institution, like the farm at the Putney School. What Woodstock maintained was a perpetual fantasy of farming, in the form of a peripheral farm operation, even after the school hired a fulltime farmer in 1958. However the tradition of a student work program, cleaning and feeding the community every day, remained a focus of school life ‑‑ and sometimes a source of friction ‑‑ throughout its history.
The first WCS catalogue concludes with a characteristic Ken Webb passage: "This 1946‑47 catalog of the Woodstock Country School was written at the end of the school's first term. A comparison with the [prospectus], issued before the school had started, will show minor changes in what we had hoped to do. The deviations from the script, however, are mainly the result of extemporization to meet an unforeseen situation and are proof of a desirable flexibility. Parents who wrote us or talked with us during the Christmas vacation were as enthusiastic as the students about a school where they treat you like human beings: you have some freedom, but you work harder than you ever did when everything was forced on you.”
Being treated like a human being was always at the core of being at Woodstock, although its meaning was not constant. The real education, which the catalogue only hinted at, was social, in the broadest sense. The egalitarianism implicit, for example, in calling teachers by their first names was a little unsettling for many students at first. Even in Syposium the traditional "Mr." and "Mrs." prevailed for most teachers, but not all. The first name style was always one of the hardest aspects of Woodstock life for outsiders to accept. They usually complained that calling teachers by their first names demonstrated a lack of respect. Given time, they often came to understand that the opposite was true. The formalism of respect so ritualized in other schools often masked a profound disrespect of teachers and students for each other, behind a hypocritical facade which bred cynicism. Seeking to avoid that, the first name basis at Woodstock, while expecting genuine civility, still left teachers and students alike free to win or lose respect on the basis of the authenticity of their actions and qualities. They were all directly responsible for their own behavior, and so could learn to value others ‑‑ and themselves ‑‑ not for the superficialities of age or rank, but for whatever goodness was in them.
Just as fundamental to Woodstock life was coeducation. The word does not appear in the catalogue, which defines the school as "a college preparatory school for boys and girls" on the title page and then says no more about the genders. But there they are in all the pictures, boys and girls together ‑‑ boys and girls very decorously together to be sure, but together in classes, together in meetings, together riding horses, together feeding turkeys, together singing around the piano. Some other "coeducational" schools of the time prohibited boys and girls from holding hands, and even the Putney School kept its students tightly scheduled in an effort to keep their energies appropriately channeled. But at Woostock, coeducation was an expression of sexual equality and integration, as boys and girls were together in every part of the school except the dorms. Yet the catalogue does not discuss the way coeducation suffused daily life at the school. Nor does it discuss the underlying reason: that emotional growth was just as important as intellectual growth, with the implicit corollary that to achieve real emotional growth, young people must be free to have real emotional relationships with each other.
This side of the school, the students' non‑academic life, was David Bailey's main responsibility, by mutual agreement with Ken. David was more relaxed about it all than Ken would have been, so that even as Ken was summing up Woodstock's first term with public optimism in the catalogue, he was already having private misgivings about his working relationship with David, and its effect, good and bad, on the school.


“Well, we got our school going, and then began the most grueling three months I've ever spent. Thank God the organization period is over now, and with the three wks at Xmas, I have been able to get rested. Arranged with David to handle by myself the promotion and town relations, to keep a voice in matters of major policy, teachers, etc., and am now much happier, more relaxed, and interested again in the school. I've made adjustment to the different attitudes of David, and see how I can work around them, eventually bring the school out to about the position 1 want it to maintain. It gives me really exactly the position I want, for 1 am quite free, quite able to cultivate contacts on the outside without keeping my nose too closely to the grindstone. Then I have the camps in which to exercise complete executive power which is also pleasant. 1 really think that David's casualness is making of the school a more deliteful place for kids than it might have been with me ‑‑ 1 guess not, but a splendid atmosphere has certainly been created.”
‑‑ Ken Webb, Diary entry, January 15, 1946

“The school was pretty disorganized, I think. I came from a school which was very rigid, very organized, and I remember there were all kinds of problems in deciding what the rules were. I remember one of the big controversies early on was whether or not students would be allowed to smoke, and then where they would be allowed to smoke. The final compromise was to have a smoking area by the flagpole, so all the kids who smoked had to go up to the flagpole. Instead of making a rule that you could or couldn't smoke, what they did was to make smoking as unpleasant as can be. David smoked like a chimney, so he wasn't one who could enforce smoking rules, but Ken didn't smoke and I remember there was a real kind of democratic process that went on, meetings and discussions, and I think that that decision about having a smoking area came out of these meetings. That first year there was a lot of that process, where things would be talked out and 1 have the sense that there was a lot of byplay between Ken and David about the way things should be run, and I have the sense that there were a lot of times when they weren't together.”
‑‑ Jim Barter '48, Interview, February 21, 1985

“There was tremendous rivalry between Ken Webb and David. Not any outright competition, just that they were very different people. Ken was kind of a square, he didn't smoke, he was a very different man from David. Ken wasn't at all interested in sports, although yes, he'd be outdoors chopping wood. David used to read the box scores as soon as he'd get the paper, the first thing he'd turn to would be the Red Sox. Most of the kids really liked David and didn't like Ken and it was kind of unfortunate, although David never slandered Ken at all. Never that 1 remember did he ever speak badly of Ken. But they were such different people that they were destined to part. 1 mean Ken Webb would seem so out of place at a cocktail party and David, that was David's natural habitat.”
‑‑ Roger Phillips '49, Interview, May 17, 1984

Of all the differences between Ken and David, none was more important than the way they related to students. Ken worried in his diary about his relationships with students, he fretted about not liking them and their not liking him, but he was never able to resolve the difficulties, least of all to his own satisfaction. While he certainly had some friends among the students and was widely respected as a teacher, he was also the butt of communal jokes. No headmaster, least of all a co‑director with an integral, powerful rival, can easily survive in such an atmosphere (as other heads of the Country School, even without rivals, would learn again in later years).
David, on the other hand, liked adolescent young people. He enjoyed their company, their struggles, their freshness, their difficulties, and all the messy and charming loose ends that go with the age. He revelled in the challenge of getting a troubled child to come out all right, and most of all he believed that the school could do better with most kids than their parents could. Although he played games with the students ‑‑ sports, parlor games, bridge and chess, as well as more complex mind games ‑‑ he was never trying to be one of them. He always maintained a certain distance as the adult, the authority-figure, the headmaster, no matter how teasing and silly his behavior might get. For many, perhaps most Country School students, David's character, with all its contradictions, surprises, inconsistencies, offered a vital, pleasant, or at worst neutral center for a school experience that was more exciting and varied than most students had ever thought possible. People who knew Woodstock in its best periods over 30 years commonly use words like "paradise" or "magic" to describe the experience. Even Peggy Bailey, David's wife, who sometimes considered David's flexibility in his dealings with the children too lenient, nevertheless acknowledged that "with all his faults ‑‑ God knows we all have faults ‑‑ David had this kind of magic touch with the young," which eluded her description and remained essentially mystical. (David Bailey's style is explored more fully in Chapter 3.)
For all his real or imagined inconsistencies and contradictions, David's values were universally perceived as different from those of Ken Webb, whether for better or worse. Their fundamental difference was that Ken believed students should be taught and therefore discipline should be imposed by others, whereas David believed students would learn to learn and therefore self‑discipline should be encouraged, even at the risk of self‑indulgence. In practice, their differences rarely seemed so stark, but were expressed in more subtle gestures of nuance and emphasis, of personal style. And it was David's style, his "casualness" that made Woodstock such a "deliteful place... (with a) splendid atmosphere," as Ken observed at the end of the very first term. Even then Ken was giving ground to David's "different attitudes" rather than challenging them, though he still hoped to work around them to make the school conform more to his own vision somehow, some day. While it would be another two and a half years before he was fully separated from Woodstock, Ken would never again seriously challenge David's authority in the school. What is strange about their relationship is not that they should contend for control of the institution, but that the contest should be so covert between them and, at the same time, so keenly‑felt in the school community.
As Ken remembered it years later, real communication between him and David diminished to a minimal level within a few weeks after Woodstock opened. Ken did not write in his diary at all during that first term, but by the winter he was clearly detaching himself from too close involvement in the school. Only a few months before, his optimistic five year plan for the school had been followed by a second five year plan. By January 1946, he was thinking of five years as his maximum commitment to the Country School: "This five years will be very pleasant, I am sure, for David and I have found out how to work together. Then when the five years are up, I'll have a following to call on for help with the cooperative school” [which Ken planned for years at Camp Timberlake, but which never came into being]. For all his repeated optimism about learning to work with David, Ken seemed more engaged in psychological cheerleading to keep his own spirits up than in making an accurate assessment of day to day reality, in which most of the school looked to David for the final decision in disputes. Insofar as Ken believed his own optimism, he was effectively denying his workday reality. By the end of that first term, the struggle for control of the school, which would seem to others to take years, was effectively over ‑and David had won. Woodstock was becoming David's school.
There is no evidence that Ken and David ever seriously tried to resolve their differences. Nor is there any evidence that Elizabeth Johnson, Owen Moon, or anyone else with influence with either man ever sought to bring them closer together. There was no explosion, no confrontation, no effort to clear the air, not just in 1945, but for the rest of both of their lives. As Ken put it, "We never had a fight, never came to blows, never had anything of that sort. We were just not on the same wavelength." So like good, stoic New Englanders, they colluded in unspoken denial and carried on as if there were no differences between them, or as if those differences would somehow resolve themselves, or as if those differences didn't really matter. They acted as if no one could see the differences between them, when of course anyone who looked could see them plainly. While they might persuade themselves that they were keeping their conflicts hidden, it was an illusion to think they could hide that reality from 35 bright adolescents, many of whom had long since learned to sense much subtler signs of trouble in their natural families. While denying their differences allowed the co‑directors to believe they presented the appearance of unity, in practice there was no way to hide their conflict as the community struggled to decide what kind of school it was. Among the issues which clearly put Ken and David on different sides were smoking and editorial freedom for Symposium.
Given his own way, Ken would have prohibited smoking altogether. But because David and other staff members smoked heavily, as did many students, and even more because Ken believed in the democratic process for the school, it was an issue he could not win. Nevertheless he kept trying, recording in his diary on February 2, 1946, "The school meeting decided to shelve the constitution for two months at any rate, which gives us the best setting for the few but important changes which I feel should be made next year. One will be restriction of smoking to recess and a half hour after supper, and only on the porch [of Greenhithe]." As it turned out, that constitution never came off the shelf, and smoking was never so restricted.
As the faculty advisor for Symposium, Ken warned the students not to publish a mocking account of local Halloween festivities, for fear of offending local sensibilities. From the start Ken had been more worried about town‑gown relations than David, and Ken wanted the school to play an active role in the community (though never quite spelled out how the school could do that). With the Halloween account blocked, the student editors appealed to David He told them he saw no harm in it and had no objection to seeing it in print. Years later this contradiction still rankled Ken, even as he acknowledged that he and David had never discussed the issue: "I never brought it up to him. It was done, there was no point in pursuing it. I didn't want to have an open fight with him. I wanted to get along as best we could. So I guess a number of times I gave in when maybe I shouldn't have. But it seemed best in the long run to do that. I didn't want to see the school go under when I left it."
When Ken and David did work jointly on a problem, there could be an odd tentativeness to their approach, as when they realized that each of them had independently decided that they did not wish to re‑hire social studies teacher Bert Sarason. Although Bert was bright and able enough (he went on to a position as an assistant professor of English at New Haven State Teacher's College), the co‑directors perceived him at 21 having a hostile spirit, a chip on his shoulder all the time ‑no doubt having heard about his classroom digressions. When the issue first came up in January 1946, Ken and David merely talked to Bert, about whether or not he should return to the school the following fall. A few days later, they talked to Elizabeth Johnson about the problem. Ken wrote in his diary that "she said definitely that we should make a change now without any doubt. So we will... It is a great relief to me, for I had said that we should, but was uncertain whether to force the issue." Even so, they hesitated. Five days later, Ken recorded that he and David "decided definitely to refuse Bert a contract for another year. Feel better now that we have, tho also regretful." But it was still not finally done for another eleven days, having taken three weeks.
Another area of fundamental difference between David and Ken was religion, though it remained diffuse. The Webbs were devoted Quakers, and Ken surrendered the idea of having a Quaker school only slowly, as his efforts at friendly persuasion proved fruitless. David was neither an anti-religious man, nor an overtly religious one. He was an Episcopalian. As long as he ran the school, there was chapel every morning, vespers every Sunday, and the usually mild, pro forma religious flavor common to baccalaureate, commencement, and similar occasions. But there was never any question that Woodstock would be anything but nominally Christian in a nominally Christian society. For David that meant a lack of ritual or dogma and a broad tolerance of diversity, a spirit of confident acceptance rare enough in secular life.
When it came to enforcing school rules, this same tolerance on David's part caused constant friction with Ken. The issue almost came to a head in November of the school's second year, when Ken caught a trusted senior hunting deer at his camps in Plymouth. The student was Bob Green, the Navy veteran, who who had taken on extra responsibilities helping to run the boys dorm. Ken wanted him dealt with harshly. David felt otherwise and his more lenient view prevailed. (The following February, the faculty would vote 7‑2 to expel another student, and David would still keep him as well, albeit on strict probation.) Some weeks after the Green episode, Ken wrote glancingly about it, and about the effort he was making to improve his relationships with students, concluding: "I like the kids better, like the chance to talk with them, and I think that gradually I am going to see a definite change as I see indications now of a change in attitude toward me. In fact, tho Susan and I were disgusted with the handling of the Green case and ready to quit the end of the year, this afternoon's faculty meeting with its struggle over the question of smoking rather restored our faith that all lesser problems can be worked out on as rational a basis. What I should like to do is stay with the school in present capacity one more year. Not only will I learn much more about the problems of a school, but it will be so good for me to work out my own problems of personal adjustment, and that problem has got to be worked out before we begin our school. I can have a radiant, gay, and loving personality if only I can let the best in me keep ascendency all the time."
That was as close as the Webbs came to precipitate action. Their leavetaking from the school was long and gradual, so gradual in fact that Peggy Bailey couldn't remember "whether it was at the end of the second year or the third year that Ken Webb withdrew from the school." Even Ken's daughter Sukie, a Woodstock student for the first four years, had no sharp memory of his departure. She said his leaving caused no significant shift in the school, that to her Woodstock seemed the same during all her time there. Others also have trouble recalling the chronology of Ken's leaving, and with good reason, since Ken detached himself slowly, by degrees, as he gave over the day to day running of the school to David, while focussing his own energies increasingly on program organization, public relations, and fund raising (and he found even his work of choice becoming harder and harder during the second year). At the same time he was increasingly distracted by the demands of his growing camps (there would be six in all). In January 1947 Ken decided that he would leave the school, in April he formally resigned as co‑director and vice president of the Trustees. The board accepted his resignation and created the one‑year position of field director for him for 1947‑48, meaning that he spent most of his final year with the Country School off campus, away from David and the students.
Thirty‑five years later, after David's emphysema had forced his own early retirement, after the school had closed, after David had died, and after the Webbs had retired from their successful camps which are now run by the Farm and Wilderness Foundation – Susan Webb thought the most difficult difference between Ken and David had been their views of "discipline." In their joint interview, the Webbs summed up their Country school experience this way:

Susan Webb: "Ken's feeling was that if somebody was caught smoking, you might give them one chance to improve, but you didn't give them two. They went out. And we weren't afraid to. Ken felt strongly that if a person agreed not to smoke at the school but continually did it, that he was simply thrown out of the school. Just as we send a boy home from the camp here, because he knows he's agreed not to smoke when he comes and we find that he's doing it. He undoubtedly has other problems, too. But David wouldn't do that. David would not clamp down. And I think also that David was very popular with the students because he wasn't firm enough. When it came to that, he wasn't firm enough with himself, if you don't mind my putting it that way. And Ken is a very disciplined person."

Ken Webb: "There were many ways in which we shared common ideals. But I did believe in discipline. I did believe in structure. And he didn't believe in discipline of any sort, apparently. Of course that's what finally did the school in. He believed in this structure‑less education with everybody doing what everybody wanted to do. I believed in structure. Not a repressive structure, but enough to keep things going along the right road."

Susan Webb: "I've always ‑Felt that if I had been able to change anything, it would have been to put in a stronger feeling of Quaker leadership. Because I think then we would have had the strength of Quaker meetings behind us, and the Yearly Meeting, and we would have had certain standards that had to be met. And I think that would have been a good thing for that school."

Ken Webb: "I would have changed the relationship between David and me. Instead of trying to be co‑directors, which is impossible, we would have had it out as to which would be head of it. And I think that since, really, it was my idea and my reputation that got the school going, I would have insisted on being head, and having David as second in command, assistant.. I think that would have entirely changed the character of the school."

Susan Webb: "And I think we would have given more. You know, I always say that there are some things that you simply, you answer 'No' to, and you have to have the courage to do it."

Ken Webb: "I think we had determined to leave because the camps were growing so, there were six camps, and we just couldn't manage all that and be proud of the school, too. So I thought it was foolish to bring this all to a head, since we had to leave anyway ‑‑ and I'd never change David."

Susan Webb: "Yes, we had to choose. But I think, really, Ken was unwilling to open up all the disagreements, all the difficulties between him and David. It would have torn the school apart, not only the school but the town, we felt, because of loyalties to the Baileys and the whole situation there. And it would have been so difficult that it was easier for us ‑‑ perhaps it wasn't the best decision, but it was the quietest and most sensible way as we could see it at that time. But I know it's worked out better for us in the long run."

Ken Webb: "Well, of course I believe in calling a spade a spade, if you've got to go into that. But with us, we didn't see that we would gain anything by it, and it would probably destroy the school, because nobody wants to go into a school or put kids into a school where there's a row going on. And that was the reason I never went around to people who helped start the school to explain why I was leaving. And I've always felt guilty that I never cleared that with them. And yet I couldn't do it without seeming to be talking about a split in the school, and it wasn't that either."

Susan Webb: "We didn't tell them all this kind of thing. But we never felt we lost by that."

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