2. Berkshire Summit House & Tower (1930-1978)

Berkshire Summit House & Tower opened in 1929, operated by North Adams businessman Georgie Phelps. After the state designated Route 9 as “The Berkshire Trail” in 1919, automobile tourism through Windsor grew. Berkshire Summit House featured a 40-foot wooden observation tower and sold lunches, postcards, souvenirs, and gasoline. The tower was blown over in a windstorm in 1932.

 

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1. Jerome Estes Store & Post Office (1895-1919)

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3. Hill Cemetery (Est. 1774)