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Things to do in Great Barrington

The Housatonic River flows through Great Barrington, with access points at Park Street in nearby Stockbridge and at the Sheffield Covered Bridge.  Almost 4 miles of the Appalachian Trail also pass through the community.

To the east of town, Beartown State Forest is popular with a variety of outdoor enthusiasts.  The site hosted CCC crews in the 1930s to cut the trails, build roads and structures, and create Benedict Pond.  A popular day-use and fishing spot, the area also features camping, swimming, boating, and picnicking, along with ORV/ATV and Snowmobiling multi-use trails. 

North of town, Monument Mountain Reservation provides scenic vistas across the Housatonic River Valley. Nathaniel Hawthorne and Herman Melville, the 19th-century authors, shared a picnic at the site and discussed Melville’s ideas for Moby Dick. 

  • Public Land
  • Private Land
  • Bus Route
  • Trail
  • Major Trail

Clubs, Retail & Rentals

Looking to meet up with others for team sports or group activities? Check out our list of clubs and leagues in the Berkshires. We also link to an array of outdoor recreation resources: retail shops for gear, rental facilities for equipment, and guides to get you where you want to go! Our list of summer camps will help you plan an overnight or day camp adventure for your young ones.