Cycling the Berkshires: Great Barrington to Stockbridge

Date and Time

Saturday, August 27, 2022, 10:00AM - 2:30PM


Great Barrington, ma,
Massachusetts, Berkshires,


Registration is required for this activity.

Registration opens Jun 27, 2022 at 12:00 PM


If you've never experienced the Berkshires on a bicycle, it's about time you did! This challenging 38-mile ride takes place in the southwest corner of the Berkshires, starting in the bustling town of Great Barrington. We will cycle on quiet but hilly roads through Alford, West Stockbridge and Stockbridge, with 2600 feet of total elevation gain. The scenery is spectacular and well worth the sweat. This ride is suitable for experienced riders who are comfortable on long rides with many climbs. We will sustain an average riding pace of 12-14mph.

AMC Trip Policy

COVID 19 Information: As of December 1, 2021 AMC requires volunteers be vaccinated or receive a negative PCR test within 72 hours of the start of an event. AMC relies on the honor system for compliance. Participants may be required to wear masks, provide proof of vaccination, or in the alternative a current (within 72 hours) negative PCR test as a condition of attending this event. For your personal safety, you should expect to be in the presence of vaccinated and unvaccinated people in all AMC settings and should make choices about participating accordingly.



Click map for driving directions


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 Chair of the AMC WMA Chapter and a bike trip leader. Brant 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.


Robyn has been leading group rides for the AMC Western MA and Boston chapters since 2005. She enjoys introducing newcomers to the sport. She also has ten years of experience as a group exercise leader, in a variety of settings. When not cycling, Robyn enjoys hiking, cross-country skiing, boot camp, and snowshoeing.


Steve has been road cycling most of his life, leading group rides for the past 17 years for the AMC. He is well-versed as a bike mechanic and is an advocate for safe riding, teaching others not only the rules of the road, but how to maximize the enjoyment of the sport. He typically rides over 2000 miles per year, including some rides during the winter months. When not riding, he can be found hiking, snowshoeing, and Nordic skiing.