Things to Do in Great Barrington MA โ€” Bucket List

Numbers 105-125

By Berkshires Macaroni Kid June 11, 2019
Whether looking for things do in Great Barrington MA for kids, parents, grandparents, etc. we’ve got a list that has something fun for every member of your family.

NOTE: As the state releases new guidelines, please practice social distancing guidelines and know that we try to keep these lists as updated as possible. Many sites and venues will not be opening for the summer so please call ahead before going. If you see a change please email

Great Barrington (105-125)

  • Hike the trails at Fountain Pond State Park (Berkshire South), Great Barrington, featuring bridges and boardwalks to keep your feet dry in the wet areas. (FREE)
  • Climb upon the modern play structures at Giggle Park, Great Barrington, that give this playground an almost sculptural feel. Giggles guaranteed! (FREE)
  • Stop by the Old Trinity Church, now known as the Guthrie Center, Great Barrington, to see where Alice’s Restaurant came into being or to enjoy an authentic Hootenanny.
  • Volunteer with your eco-conscious kids at the Housatonic RiverWalk, Great Barrington Earth Day cleanup. (FREE)
  • Partake in a day of swimming and sandcastle-building at Lake Mansfield, Great Barrington, a 29-acre lake surrounded by the 29-acre Lake Mansfield Forest. There's also an old fashion jungle gym and plenty of hiking trails to enjoy. (FREE)
  • Venture along one of the county’s most well-traveled hiking trails to the Squaw Peak summit of Monument Mountain, Great Barrington, with sweeping views stretching from the Catskills to Mt. Greylock. (FREE)
  • Play on the swings or relax on the shaded benches at Muddy Brook Elementary School, Great Barrington after a long hike at Monument Mountain, or explore the nearby pond with your budding scientists. (FREE)
  • Experience some fall fun at Taft Farms, Great Barrington, pesticide-free family farm, featuring hay rides, a corn maze, a pick your own pumpkin patch and more.
  • Explore the Upper Housatonic Valley African American Heritage Trail, South Berkshires, a mapping of 48 sites, throughout 29 Massachusetts and Connecticut towns, celebrating local African Americans who played roles in shaping our nation's history. (FREE)
  • Learn about the early life and Great Barrington public school education of the Civil Rights leader, prolific author and recipient of Harvard’s first African American Doctoral graduate, W.E.B. Du Bois at the  W.E.B. Du Bois Center, Great Barrington, and explore the African American experience and issues regarding social justice. (FREE)
  • Stop in at Windy Hill Farm, Great Barrington for some fresh pressed cider or visit the holiday shop for fresh-cut winter greens.
  • Attend a kid-friendly concert at the Great Barrington Bandstand. (FREE)
  • See a full-scale production, take in a concert or screen a movie at the historic Mahaiwe Performing Arts Center, Great Barrington.
  • Bowl a few frames at Cove Bowling or check out their Cosmic Bowling on Friday and Saturdays.
  • Check out your family's skills on the climbing wall at the Kilpatrick Athletic Center at Simon's Rock.
  • Visit the Great Barrington Farmers Market for some fresh produce or a fun crafting or cooking class courtesy of the Berkshire Co-Op Market. Or signup for one of these classes during the cooler months at the Co-Op.
  • Stroll the Great Barrington Fairgrounds or visit when a fair or festival is taking place on its grounds.
  • Follow the Railroad Street Youth Project on Facebook to learn of their many programs and events.
  • Play and laugh at the Muddy Brook Elementary School Playground.
  • Find free family fun at the Mason Library all year round from storytimes and playgroups, to book clubs, performances and more.
  • Schedule a day of winter fun at Butternut Ski Area, Great Barrington, featuring 22 downhill ski trails on 110 skiable acres, 11 lifts, two terrain parks, an 8-lane Tubing Center, and a full-service ski and snowboard shop.