RambleFest Weekend in Adams: Street Festival Sunday, 58th Greylock Ramble Hike Monday
Live music, local beer, vintage train rides, and a campfire on Sunday lead into the 6.6-mile hike up Massachusetts’ highest peak, with free shuttles.
Sunday–Monday, October 11–12 | Adams, MA | Free
RambleFest takes over Adams through the holiday weekend with a street festival on Sunday and the annual Greylock Ramble hike to the summit of Mount Greylock on Monday. ProAdams, the town’s nonprofit economic development group, organizes both.
The festival
The festival is held outdoors at the Adams Visitor Center, 3 Hoosac Street, rain or shine, and admission is free. It has live music, local craft beer and wine, food, produce, outdoor recreation, and craft exhibitors.
Local beer has been part of RambleFest since the first one, organizers say, and Antimony Brewing of Lenox pours Ramble Wolf. Non-alcoholic options include cider from Adams’ own Jaeschke’s Orchard. Food comes from La Chalupa y La Enchilada, Dough Boys Pizza, Bezzle’s BBQ, and the Adams Lions Club.
Kids can decorate pumpkins and roast marshmallows at a campfire. Community groups set up tables, among them the Adams Historical Society and St. Stanislaus Kostka School, and vendors include O’Lo Creek Farm, with goat’s milk soaps and beeswax candles, and Tamarack Hollow Nature & Cultural Center, which sells wildcrafted evergreen products and nature books. Tamarack Hollow also performs with the Berkshire Rhythm Keepers from 1:30 to 2pm.
Berkshire Scenic Railway runs rides on its vintage Hoosac Valley Service cars from Adams Station, directly across Hoosac Street, all weekend.
The Hike
The Greylock Ramble has been held every Columbus/Indigenous Peoples Day since 1965. Hikers take the Cheshire Harbor Trail, the gentlest route to the 3,491-foot summit, a 6.6-mile round trip that takes four to five hours and is moderately strenuous.
Free shuttles run from the Adams Visitor Center to the Greylock Glen Outdoor Center from 8am to 1pm, with returns until 4pm. Organizers strongly recommend using them, since parking near the trailhead is very limited. Certificates of accomplishment are free at the summit.
The Ramble started in 1965 as the first project of Operation Wonderful Town, a volunteer group set on bringing visitors to Adams in foliage season. The first one drew 600 hikers, and more than 1,000 cars of spectators came to watch them arrive at the top.
Adams Visitor Center, 3 Hoosac Street, Adams, MA. Full details at exploreadams.com/ramblefest.
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After a decade of writing for RI (along with many other publications and organizations) Jamie took over as editor in 2025. He has a masters in journalism from NYU, a wonderful wife, two kids and a Carolina dog named Zelda.
