TORY
CAVE
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Tory Cave is located in Lenox, Massachusetts on October Mountain or Dewey Mountain as some
people call it. There is a brook that passes it called Roaring Brook. There are
other Tory Caves located in
many different areas like Connecticut, West
Virginia, Vermont, and near Boston.
Tory
Cave
is a natural cave. It collapsed in a land slide in 1900 and all that remains is
the entrance. Before it collapsed, a person could walk through the cave and
they ended up on the other side, which would lead them to Tory
Cave
Farms. But now someone can only walk several yards into it. The entrance to the
cave is right at the bottom of the cliff which is covered with moss. In front
is a large pool with crystal clear water and a small waterfall.
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. Hence his loyalty to England.”
(T.Bosworth) a Tory was someone who sided with the British in the Revolutionary
War. Gideon Smith did that, but everyone hated him. Gideon Smith 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 Gideon Smith food (Berkshire
web.com) When the colonists found him, they roughed him up. The colonists
decided to hang Smith because he went against them. Then smith fought for the
colonists. (Wood 32)
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” (Duval 4). 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. One of the gravestones there was
his daughter’s who died as a baby. (Stockbridge Historical Room). He died in
1838, and is buried at the Church on the Hill cemetery.
The Outing Club is known to visit
the cave on many different trips. This cave is actually the most favored place
in the Outing Club because so many students want to visit it. This cave
requires good skills and walking carefully across very wet rock that can some
times be dangerous.
DIRECTIONS
From Pittsfield
turn on to Holmes road keep going straight until you see a light that is blinking
yellow. You will then see a street sign that says Chapman
Road or East
Street. If you see one of those
street signs then turn on to that street. Once on that street keep going
straight until you see a four way intersection. Then turn on to New
Lenox Road the one that has the St.Helena’s Chapel
sign. Once on that road you will see St.Helena’s Chapel and you will want to
keep going pass the church until you see a sign that says Roaring
Brook Road. Once you see that sign take that road.
You will see a bridge with water running under it and that’s the one you want
to stop at and once stopped you will see a trail.
From Lee
take Route 7 past Cranwell Resort keep going until you see a sign that says
Housatonic Street with a hardware store on the corner. Go past the hardware
store until you see a sign with a big hill that says East
Street. Turn on to that road and keep going
straight past Eastover Resort then about 4 or 5 miles from Eastover you will
see a four way intersection. Then turn on to New
Lenox Road the one that has the
St.Helena’s Chapel sign. Once you see that sign take that road and go past the
church. You will see a bridge with water running under it and that’s the one
you want to stop at and once stopped you will see a trail.












