Cycling in the Berkshires, MA

Cycling in the Berkshires

Cycling enthusiasts visiting the bucolic Berkshires have a plethora of options to explore. The region's terrain offers exhilarating challenges and breathtaking vistas. Cyclists can explore charming towns, tackle steep climbs, and relish the stunning beauty of Western Massachusetts. Scroll down for links to Berkshire rides on mountain biking and road biking apps.

  • Public Land
  • Private Land
  • Bus Route
  • Trail
  • Major Trail

What to know before you go

Ride with GPS: Visit HERE for a presorted list of routes in Berkshire County.

Strava: Visit HERE for a selection of segments in Berkshire County (login required).

Trailforks: Visit HERE for Berkshire County mountain bike trails.

Please visit our SAFETY TIPS page before heading out to enjoy the Berkshires!

Clubs, Retail & Rentals

Looking to meet up with others for team sports or group activities? Check out our list of clubs and leagues in the Berkshires. We also link to an array of outdoor recreation resources: retail shops for gear, rental facilities for equipment, and guides to get you where you want to go! Our list of summer camps will help you plan an overnight or day camp adventure for your young ones.