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Tuesday, March 3, 2026
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Last updated Friday, February 27, 2026
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About Brookline
A few miles north of Brattleboro in Windham County, Brookline is a small hill town that has resisted the commercial development that transformed its larger neighbors. Chartered in 1794, the town was settled late by Vermont standards, and its hilly terrain and lack of water power meant it never developed a significant industrial base. The population has always been small.
Brookline's round schoolhouse, built in 1822, is one of only a handful of round schoolhouses surviving in the United States. The building, now on the National Register of Historic Places, reflects the experimental spirit of early Vermont education -- its designer believed the round shape would improve acoustics and eliminate corners where students might hide from the teacher's gaze.
With roughly 517 residents, Brookline operates under the selectboard and town meeting system. The annual meeting is a gathering small enough that every voice is heard without a microphone. Brookline's residents have chosen, generation after generation, to maintain their town's independence rather than merge with a larger neighbor -- a quiet act of civic commitment that speaks to the Vermont tradition of local self-governance.
Sources: Wikipedia
See an error? Email hello@govermont.co · Data sourced from Vermont Secretary of State