Tory Cave is a natural cave in Lenox on the Roaring Brook Trail, part of October Mountain State Forest. It collapsed in a land slide in 1900 and all that remains is the entrance. Tory Cave got its name from a man named Gideon Smith because he was a Tory. “The British made Gideon Smith an officer in the British Army by proclamation of the king during the French and Indian War. Tory. “The British made Gideon Smith an officer in the British Army by proclamation of the king during the French and Indian War. He owned a tavern in Stockbridge named Gideon Smith Inn which is now Wheatleigh. In May 1776, he harbored a British prisoner of war, which was a crime. Gideon Smith spent many weeks hiding out in his house, but after that, he heard that the colonists knew where he lived so he went to hide out at Tory Cave. The Indians brought him food.

Gideon Smith died at the age of 98. One of his sons also fought for the colonists in the Revolutionary War. His obituary says that “for several years he was little known except in his family and neighborhood” There is a small burial ground in Stockbridge (across from Wheatleigh) on land that he sold and said in the deed that it would have to stay as a burial ground. Smith is buried at Church on the Hill cemetery.

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