Best Bicycling in the Berkshires Weekend 2023

Date and Time

Friday, September 8, 2023 5:00PM - Sunday, September 10, 2023 3:00PM


Sheffield MA,
Massachusetts, Berkshires,


Registration is required for this activity.


New for 2023! Join us for a full weekend of bicycling adventure in the Berkshires! Participants will stay for two nights at the Race Brook Lodge in bucolic Sheffield, MA. On Friday afternoon at 5pm, we will gather for a happy hour at the bar where you may purchase beverages and/or snacks, get to know one another, and learn all about our weekend. Following our happy hour, we will enjoy a wonderful dinner which is included as part of this event. On both Saturday and Sunday after enjoying a fully included hearty breakfast, we will offer a choice of two bicycle rides, one intended for riders who prefer shorter rides (under 20 miles) with less hill-climbing (activity level will be Easy), and the other intended for riders who enjoy longer rides (30-45 miles) and are comfortable climbing significant hills (activity level will be Moderate or Vigorous). All rides will be led by trained and highly experienced AMC volunteer trip leaders. Cycling routes will feature paved rural roads, minimal automobile traffic, and eye-popping scenery! And of course, after cycling on Saturday you will enjoy a second fully-included and delicious dinner on Saturday evening. Sheffield, MA is approximately 2.5 hours by car from either Boston or NYC. Advance registration with payment is required on or before June 4, 2023.

AMC Trip Policy


Adult: $418 member / $468 non-member
*All prices include * Two nights lodging at Race Brook Lodge (in double occupancy room); * All rooms include private baths; * Full dinners on Friday and Saturday evening; * Full breakfasts on Saturday and Sunday morning; * Access to Lodge amenities including outdoor pool and hiking trails. Prices DO NOT INCLUDE: * Alcoholic beverages during dinner or at Friday's happy hour; * Beverages or snacks during visits to the bar; * Lunches on Saturday and Sunday

Related Link(s):

Race Brook Lodge

Click map for driving directions
Janine, Monument Valley Road


Bicycling - Road

Offered By

Western Massachusetts






Adults (18+)


Brant is a trip leader for the AMC Western MA Chapter Bicycling Committee. 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 3000 miles each year. His bike is named Ulysses, inspired by the final line of the poem by Tennyson.


Steve has been road cycling most of his life, leading group rides for the past 20 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 1500 miles per year, including some rides during the winter months. When not riding, he can be found hiking, snowshoeing, and Nordic skiing.


Janine is Chair of the AMC Western MA Bicycling Committee. Prior to starting the AMC Western MA 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.


Robyn has been leading group rides for the AMC Boston Chapter since 2005. She enjoys introducing newcomers to the sport and also leads rides for a Meet Up group. 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, and snowshoeing.