The Top 16 Attractions around Cheshire
There are plenty of places to see and visit around Cheshire. Whether you love hiking or cycling, Cheshire is a region where 16
hidden gems are waiting to be explored and visited. Check the top places to visit in the region and plan your next adventure today.
hidden gems are waiting to be explored and visited. Check the top places to visit in the region and plan your next adventure today.
Last updated: October 12, 2025
Visible from afar, the Veterans War Memorial Tower at the top of Mount Greylock was erected in 1934 in memory of all who served the U.S. during World War I. …
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The Bascom Lodge was built in the 1930s at the summit of Mount Greylock. It was managed by the Appalachian Mountain Club for 16 years until 2000 when it came …
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Converted from an old railroad track, the Ashuwillticook Rail Trail is now a 10 foot wide, 14.2 mile, paved multi use trail meandering along the Cheshire Reservoir while offering sublime views of Mt. Greylock.
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The Thunderbolt Shelter was built in 1940 as a warming hut for skiers using the Thunderbolt Trail. This historic stone building is currently only used as a winter/emergency shelter for those attempting Mount Greylock during the off-season.
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The U.S. Bicycle Route 7 (USBR 7) is a super good, north-south bike trail that follows the Western New England Greenway through Connecticut, Massachusetts, and Vermont. This section in Massachusetts …
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Most popular routes around Cheshire
Most popular attractions around Cheshire
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