The Top 20 Attractions around Pittsfield
There are plenty of places to see and visit around Pittsfield. Whether you love hiking or cycling, Pittsfield 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: November 30, 2025
Ashuwillticook Rail Trail
Highlight (Segment) • Trail
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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U.S. Bicycle Route 7 — Cheshire Reservoir section
Highlight (Segment) • Cycleway
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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Cheshire Reservoir
Highlight • Lake
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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Mount Greylock State Reservation Visitor Center
Highlight • Rest Area
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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Olivia's Overlook
Highlight • Viewpoint
Stockbridge Bowl is also known as Mahkeenac Lake This is a 372 acre artificial lake.
It is also the location chosen as the summer residence of the Boston Symphony Orchestra. …
It is also the location chosen as the summer residence of the Boston Symphony Orchestra. …
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