The Top 20 Attractions in Berkshire County
There are plenty of places to see and visit in Berkshire County. Whether you love hiking or cycling, Berkshire County is a region where 20
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 6, 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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Located just north of Adams, the Ashuwillticook Rail Trail Head sets a lovely tone for the rest of your ride along the trail, perfectly smooth and easy to use for families.
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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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The Gould Trail is a popular route to the summit of Mount Greylock, the tallest mountain in Massachusetts, up its eastern flank. This trail climbs up through hardwood forests, which are exceptionally beautiful in the fall, parallel to Peck's Brook.
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Cheshire Reservoir captivates riders with its tranquil beauty. The scenic reservoir, nestled in the Berkshires, offers stunning views along the route. Cyclists can enjoy a peaceful ride surrounded by nature, …
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The Mount Greylock State Reservation Visitor Center is located on the southern side of the long mountain and a great place to stop before your hike. There are people available …
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The Long Trail, the oldest long-distance hiking trail in the United States, begins at the Massachusetts–Vermont border near Williamstown, MA. This southern terminus is marked by a large wooden sign …
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