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

  • Courtyard Lenox bar.jpg

    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

  • Yankee Suites Extended Stays Pittsfield Ma

    Extended Stays

    Looking to stay a week? Month? Year? Yankee Suites Extended Stays offers fully equipped condo-style living in downtown Pittsfield. Read more

  • Yankee Inn

    Book an in-room massage

    Upgrade your next stay with the ultimate indulgence- an in room massage at the Yankee Inn Read more

Have a question about your trip to the Berkshires?

Ask Us

be in the know

Stay up to date with:

•Events •New and noteworthy happenings 
•Exclusive offers delivered to your inbox each month!

Sign Up