Fall Cycling in the Berkshires

Date and Time

Friday, October 11, 2019 5:00PM - Monday, October 14, 2019 3:00PM


Massachusetts, Berkshires,


Registration is required for this activity. Please contact leader(s).


Join us for 25-50 mile led road rides over scenic, hilly country roads on both sides of the scenic Taconic Range along NY-Mass border (10-13 mph easy pace, but intermediate hilly terrain). Enjoy the beauty and color of New England's showiest season! Previous group cycling experience in hilly terrain highly recommended, though not necessary for strong flatland cyclists. $238-$288 per person includes 3 nights lodging in a relaxing country home, 3 breakfasts, 2 happy hours & dinners Saturday & Sunday (meals fit for a foodie!). See "Cost" section below for more information. For more information or to register contact Aldo. This is a very popular trip that fills many months in advance. Cancellations do occur, wait listing advised. This trip also takes place on Memorial Day and Labor Day weekends (posted as "Spring Cycling in the Berkshires" and Labor Day Cycling Weekend in the Berkshires"). If this trip does not fit with your schedule, please check out these other weekends. (Location shown on map below is a place holder; the actual lodging location will be given to registered participants before the trip start date.)

AMC Trip Policy


Adult: $288 member / $288 non-member
*Happy hour Sat & Sun; dinner Sat & Sun; lunch fixings Sat, Sun, Mon; breakfasts Sat, Sun, Mon; accommodations Fri, Sat, and Sun (private $288 per person or $275 per person (contact Aldo for details); semi-private, $238 per person [all fees includes food previously described]).

Past participants say...

"The hills are challenging, but it helps you build up your strength and stamina. The scenery is beautiful, with one gorgeous view after another. It is peak foliage season at this time of year in the Berkshires, so the timing is great!" "Well-planned and led rides through great scenery. The lodging is comfy, the company is fun, and the food is so delicious! What a great weekend! Highly recommended."

Related Link(s):

AMC Boston Chapter Bicycling Committee Website

Click map for driving directions
Fall Colors at pondside


Bicycling - Road

Offered By



Wait Listed


Easy Pace (10-13 mph)/Intermediate Hilly Terrain


Adults (18+)


(Email this person.)

Aldo has been an AMC Boston Chapter bicycling trip leader since 2010. He is also a hiking and skiing leader, and a recent past chair of the AMC Boston Chapter ski committee.


(Email this person.)

Glenn is an AMC NY-NJ Chapter cycling and flatwater paddling leader, and also leads cycling trips for the Bicycle Touring Club of North Jersey (BTCNJ).