See the Berkshires' best with our premier Harvest Weekend Getaway. Autumnal flavors will fill your day as you traverse this gorgeous landscape, pedaling between orchards, vineyards, dairy farms, and iconic small towns. We'll see you there!
Friday, September 20th
3pm at Tanglewood
The Weekend Getaway kicks off on with a tour of the scenic roads around Tanglewood, the Boston Symphony Orchestra's summer home. We'll head to High Lawn Farm (featured on Sunday’s Gran Fondo route) and indulge in the farm's delicious, jersey cow ice cream.
Saturday, September 21st
9:30am at Jiminy Peak
37 Corey Rd, Hancock, MA 01237
Saturday’s route crosses the border into upstate New York to visit Shadowbrook Farm. We’ll meet the farmers, tour the farm, and visit the farm store before returning to Jiminy Peak for a scenic chairlift ride for lunch at the summit.
Sunday, September 22nd
9:30am at Turn Park Art Space
2 Moscow Rd, West Stockbridge, MA 01266
We suggest arriving early for a coffee at No. Six Depot Cafe & Roastery, right across from our meeting point. It’s worth a cup, plus a bag of beans to take home with you! Sunday’s ride loops south along some of our favorite roads in the Berkshires. We’ll stop in at Taft Farms for a mid-ride treat before looping back toward West Stockbridge. We’ll have lunch from No. Six Depot to bring the weekend to a close.
Tyler Wren
Farm to Fork Fitness Adventures founder (and former professional cyclist!) Tyler Wren will be with you for every turn of the pedals throughout the weekend. As your lead guide, he’ll share his knowledge of the region while fostering a rewarding group riding dynamic.
Self Guided Adventures
Can’t make it to the big event?
Get season-long access to our best routes . Our curated itinerary takes the effort out of planning so you can focus on the adventure! Explore fantastic rural roads, meet local artisans, and enjoy farm-sourced food all along the way. Learn more here.