Three people with traditional school backgrounds started the Country School as an alternative to

and improvement on those traditional institutions.  Modeled to great extent on Black Mountain College,

Woodstock opened in the fall of 1946 with a handful of students and teachers and two headmasters,

David Bailey and Kenneth Webb.  Within three years, they had fallen out largely over smoking –

Ken was a non-smoker, David was a smoker (who would die of emphysema), and David’s view was

the more popular.  Ken gracefully retreated from the Country School to focus his energies on

the Farm and Wilderness Camps that he and Susan founded in the 1930s and are still going strong in Plymouth. 

For its first ten years, the Country School campus was on Church Hill in Woodstock,

with a boys’ dorm on the Green opposite the Town Hall, and a smaller boys' dorm at the top of Linden Hill.  The school remained small (rarely more than 90 students)

and unconventional to a point (students were required to get haircuts into the mid-sixties). 

Its greatest strengths were its informality, academic rigor, and sense of community

(including doing the work to keep the community functioning day-to-day). 

In the fall of 1954, the school’s main classroom building, the Barn, burned to the ground in the middle of the night. 

Despite losing most of its classrooms, all its science labs, offices and public rooms, the school was back on

schedule before the next day was over, albeit a somewhat improvised schedule. 

After considering whether to rebuild or move to another site, David and the trustees settled on Upwey Farms

in South Woodstock as the school’s new home, where it opened in the fall of 1955

with the Upwey barn as the main classroom building, with 40 boys sleeping in the loft (later the art loft)

until French House, the new dorm on East Hill was finished. 

For most of the next ten years, the Country School flourished. 

At the same time, David was growing sicker and denying it and so not preparing well for

how the school would work when he was gone.  Rather he implemented the four-term plan

even though he would not be around to run it when it began in 1967, with interim headmaster John Holden. 

He was succeeded by the choice of a trustees search committee, Tawny Kilborne, for a couple of

tumultuous years, during which French House, the main boys’ dorm, burned to the ground. 

Tawny’s tenure ended in the summer of 1970, after a visit with board chair Tom Debevoise in Washington,

when he resigned abruptly.  By this time, under Tom’s leadership, the school had built New Dorm,

a co-ed dorm, and gone deeply into debt for the first time in its history. 

With Tawny gone, Phil Hansen, then in his mid-twenties, became interim headmaster (and later headmaster)

and faced the inherently contradictory challenge of re-creating the school almost anew. 

With little institutional continuity to fall back on, the community took a week off from school to begin defining itself. 

At the end of that week the school had a written philosophy based on a shaky consensus of faculty and students

(the trustees did not take part).    The school revived over the next several years.  By now the four-term plan

was working fairly well and enrollment was over 100 (as high as 125 occasionally).   

But the pressure of running a more complex school with a fractious faculty and unsupportive trustees

wore the headmaster down, although he managed an orderly transition to the next headmaster

chosen by a trustees search committee.  

Walter Hill took over as headmaster in January 1975, presided over shrinking enrollment and growing debt,

and resigned abruptly in the summer of 1976 as the trustees were considering closing the school. 

In the fall there was a brief possibility of Woodstock merging with the Stowe school,

but that failed to materialize, and the trustees were planning to close the school. 

Then Robin Leaver, a Stowe trustee disappointed in the failed merger, offered to take over at Woodstock

and the trustees accepted his offer. 

Four years later, in the summer of 1980, after Robin had left, a much smaller Country School closed for good.   

 Bill Boardman ’56, teacher 1971-76

 (for the reunion of August 2010)