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Berkshire Bike Routes

Road Routes

Stephentown CCW Loop


Pittsfield to Canaan Center


Ride to Southfield Store and back

The Southfield Store is a destination not to be missed, great coffee, tasty baked goods and awesome lunch options.  Paired with some beautiful quiet roads,  this is one of our favorite summer rides!

Just the Alford Loop clockwise

Classic 20 mile route from the Great Barrington shop takes you through Alford, beautiful vistas and quiet roads makes this a favorite ride.

Gravel Routes

Hard Packed Dirt and Gravel


W. Stockbridge Dirt Adventure


Austerlitz - Harvey - Beebe Gravel


Sheffield - York - Campbell


S. Egremont Gravel


MTB Routes

Greylock Glen

Greylock Glen’s trail network includes multi-use trails designed to accommodate a wide variety of users with different skills and interests. Greylock Glen also serves as a gateway to the Mt. Greylock State Reservation trail system


Pittsfield State Forest

Pittsfield State Forest is a recreational state park with many mountain bike friendly trails.  Oh such fun…woohoo, link is below to Trailforks.


Kennedy Park

Kennedy park has a great network of multi use trails for all skill levels.  Beginners should stick to the Green trails within the Kennedy park proper.   Advanced MTB'ers will want to send it towards Portuguese, and climb the jeep trail to access Broken Thumb and Bob-T.  If you have packed a lunch and dinner, go for The Finger... you have been warned.

Beartown State Forest