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Architectural Monographs: Connecticut’s Charming Old Hill Towns

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Only the hardiest settlers made it through the “hideous and trackless wilderness” on the Connecticut Path to access the hills that would later be known as Woodstock, Connecticut in the late 1600s. The first of them came from Massachusetts, establishing a community that looked out over the countryside from a vantage point that protected it from altercations with the Native people and later, from industrialism.

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The location also prevented the aesthetics of the Victorian era from wiping out the simple, refined charm of the Colonial architecture in the late 19th century, preserving the earlier period. Even after stage-coach routes made the hill towns of Windham County accessible, these places retained their character. The townspeople married amongst each other, eventually creating a population that was “knit together in one great family circle.”

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This issue of the historic White Pine Architectural Monographs explores the history of this area, its standout structures, and its people. One particularly humorous anecdote recounts the story of a dark summer night in 1750 amidst fears of the French and Indians, when “a roar and tumult filled the town.”

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“The people, perplexed and greatly frightened, stayed behind barred doors and listened with horror, no one venturing out to face the foe. Next morning it was discovered that it was only a migration through the town of noisy bull-frogs in search of water, their own pond having dried up. Much to the mortification of the Windham people, the story flew all over the county and the country.”


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