The Top 10 Lakes around Pittsfield
Looking to visit the best lakes around Pittsfield? After all, there’s nothing better than the serenity of the lakeshore — or a quick dip when the weather’s warm. So, browse our list of Pittsfield’s top lakes below as recommended by the komoot community, and experience more on your next adventure!
Last updated: November 27, 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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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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Monks Pond
Highlight • Lake
Monks Pond sits in the Yokun South Ridge Reserve, hidden by the forest, accessed by a short path along the Burbank Trail. The pond has green water, offering shade during …
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