Cycling the Berkshires: Stockbridge-Alford Ramble

Date and Time

Saturday, July 20, 2024, 9:00AM - 2:00PM


Stockbridge, MA,
Massachusetts, Berkshires,


Registration is required for this activity.


If you've never experienced the Berkshires on a bicycle, it's about time you did! This challenging 32-mile ride begins in Stockbridge MA. We will cycle on quiet but hilly roads through Stockbridge, Housatonic, Great Barrington, Alford, West Stockbridge, and Lenox. These are among the most picturesque towns in the Berkshires. The planned route will involve approximately 2000 feet of total elevation gain (about 62 feet per mile), and there are several sections with grades over 5%. This ride is intended for strong and experienced riders who are comfortable on long rides involving many climbs. We will sustain an average riding pace of 12-14mph. We usually plan to be out on route for about four hours (including breaks). According to the AMC's Activity Difficulty Ratings, it is a moderate bicycle ride. That being said, while beautiful, this is also one of the most physically demanding rides that we lead in the Berkshires.

AMC Trip Policy



Click map for driving directions
Brant taking a pause in Housatonic MA


Bicycling - Road

Offered By

Western Massachusetts






Adults (18+)


Janine is Chair of the AMC WMA Bicycling Committee. Prior to starting the AMC WMA Chapter Bicycle Committee, Janine led bicycle trips for the AMC Boston Chapter for two decades. She enjoys planning and leading bike rides, taking AMC members to interesting places in Massachusetts and exploring with them by bike.


Brant is a bike trip leader. He has been riding bikes for both pleasure and exercise for as long as he can remember. Starting in the early 2000s, bicycling became Brant's primary outdoor activity (except during winter), and he now rides at least 2500 miles each year. His bike is named Ulysses, inspired by the final line of the poem by Tennyson.