- Pine Cobble School

The need for an independent school in the Northern Berkshires became apparent in the mid 1920’s. In 1928, Edgar and Doris Flinton, two local public school teachers, caught wind of these concerns and began a private summer tutoring program called The Williamstown Tutoring School. It was a success from the start and known for its strong academics combined with individualized attention, focus on the arts, and casual and friendly atmosphere, all of which remain hallmarks of Pine Cobble today. After nine successful summers, and after repeated urging by several prominent Williamstown families, most of whom were affiliated with Williams College, the Flintons opened the doors to Pine Cobble School, in September of 1937.

The School began in rented summer mansions, which were left vacant during the fall, winter, and spring. Out of necessity, and to accommodate various owners, the School moved to a different location four times in its first six years. Meanwhile, the Flintons were finding difficulty running the School at a profitable level, and so in 1940 a group of parents applied for, and were granted, not-for-profit corporation status. The Flintons continued at the School until 1943, when Dr. Flinton chose to help in the war effort by training pilots in Colorado. Pine Cobble remained in the same location from 1943 onward and continued to grow. In fact, after World War Two, Pine Cobble expanded its grades into the high school level for the only time and, in 1947, granted high school diplomas to its only graduating class. Several notable Heads of the School included Dwight Little, who served from 1950-1961, and Caroline Copeland, who served from 1961-1966.

In 1970, Pine Cobble erupted in flames, and the main building burned to the ground. There was no loss of life, as it was on a weekend, but the future of the School was in question. The School had no cash reserves, all the records had been destroyed, and there was not so much as a book or pencil with which to start anew. Luckily, the families most devoted to Pine Cobble rallied together and, while housing various grades in local church classrooms, the school was rebuilt in 1970-1971.

The 1970’s and 1980’s were marked by continued growth, most notably under the leadership of Tim Holbrook, Headmaster from 1973-1989. The School continued to be tuition-driven, however, and any capital improvements were always a stretch for the budget.

In 1989 David Harris became Pine Cobble’s twelfth Headmaster. He brought the School up-to-date by establishing many of the administrative systems in place today. Also, at Mr. Harris’s urging, Pine Cobble became a member of various accrediting bodies, including AISNE and NAIS, and the School underwent its first self-study in 1991, which called for the need of an administrative team to work with the Headmaster and divide some of the work-load for him.

In the middle of Mr. Harris’s tenure, it became apparent that the building that had been constructed after the School had burned was in dire need of major capital improvement. Also, it was becoming increasingly obvious that the School’s several acres were not suitable for any significant athletic program. Therefore, Mr. Harris and a group of trustees arranged a sale enabling Pine Cobble to purchase the campus of the HighCroft School, a proprietary boarding school a mile away whose owners were retiring and therefore selling the property. As part of the transaction, the former Pine Cobble campus became the David and Joyce Milne Public Library, which it remains today.

Nicholas M. Edgerton was appointed the School’s fourteenth Headmaster in 2000. Working as a team, the administration and Board of Trustees have embarked on a long range strategic plan to bring the School within grasp of the final stage of institutional maturity: developing a strong financial base for the present and the future.

Pine Cobble enjoys a seventy year history of academic excellence. The School has had a wonderful past and has produced many notable alumni in education, the arts, medicine, and business. Pine Cobble is poised for an even more successful future.

Heads of the school (terms):