From tearing down mountains and catching air on knolls at Berkshire East to laid-back Sunday cruising along the placid Ashuwillticook Rail Trail, the Berkshires has it all for bikers. The region has been known to attract people who move here specifically for the wealth of prime biking opportunities, home to thousands of miles of scenic roads from the extreme 2,000+ ft. ascents to the top of Mt. Greylock to the meandering quiet roads along the mountain rivers of the Hilltowns. It also is host to a growing network of mountain bike trails whether it be in one of the many extensive State Park trail systems, Jimney Peak or the Tanglewood-accessible Kennedy Park trails.


Browse all things Biking in the Berkshires

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    Getaway To The Berkshires!

    This 100% solar powered, family owned & operated hotel in Lenox is the perfect spot to getaway with the family! Read more

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    Lakeside R&R

    Stay on the waterfront with gorgeous views of Laurel Lake Read more

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    Drink, Dine, Decompress

    What better way to end your long day than with a cocktail and appetizer... in bed! the Courtyard by Marriott Lenox offers every convenience under one roof! Read more

  • Courtyard Marriott Lenox Girlfriend Getaway

    Girlfriend Getaway

    The Berkshires is the perfect place for a girlfriends notch shopping, amazing restaurants and comfortable lodging. Read more

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