Outdoor activities

in Great Barrington, MA

Discover outdoor activities in Great Barrington with Meetup. Whatever your interest, Meetup helps you connect with like-minded people.

Hiking

5th Annual Tanglewood & Optional Camping Event

5th Annual Tanglewood & Optional Camping Event

Fri, Jul 10 · 4:00 PM EDT

by North Central MA-Southern NH Hiking Group

Bear Mountain (Salisbury CT) ** please note the new date **

Bear Mountain (Salisbury CT) please note the new date

Sat, Jun 6 · 9:00 AM EDT

by Hiking Mates of the Capital Region

Ashintully Gardens

Ashintully Gardens

Sun, Jun 7 · 10:00 AM EDT

by Adirondack Hiking Photography Group

Hike Alander and Brace Mts., Mount Washington Massachusetts

Hike Alander and Brace Mts., Mount Washington Massachusetts

Sat, Jun 20 · 9:30 AM EDT

by Hartford Area Hiking™

Walking

Ashintully Gardens

Ashintully Gardens

Sun, Jun 7 · 10:00 AM EDT

by Adirondack Hiking Photography Group

Nice & Easy Walk

Nice & Easy Walk

Fri, May 29 · 10:00 AM EDT

by Appalachian Mountain Club (AMC) Western MA

Bear Mountain (Salisbury CT) ** please note the new date **

Bear Mountain (Salisbury CT) please note the new date

Sat, Jun 6 · 9:00 AM EDT

by Hiking Mates of the Capital Region

Waterfalls & Wine in the Land of Nod

Waterfalls & Wine in the Land of Nod

Sat, May 30 · 1:00 PM EDT

by Connecticut Wine Lovers

Running

Bear Mountain (Salisbury CT) ** please note the new date **

Bear Mountain (Salisbury CT) please note the new date

Sat, Jun 6 · 9:00 AM EDT

by Hiking Mates of the Capital Region

Bread Loaf Mountain to Pine Knob Loop and back.

Bread Loaf Mountain to Pine Knob Loop and back.

Fri, Jun 12 · 9:30 AM EDT

by CT Outdoors -- Sierra Club

GroupGolfer.com Special for Copake Lake 2026 - Buy Now for $19.

GroupGolfer.com Special for Copake Lake 2026 - Buy Now for $19.

Sun, Jun 7 · 11:30 AM EDT

by Golf and Tennis Serendipity Group

Macedonia Brook State Park

Macedonia Brook State Park

Wed, Jun 3 · 9:30 AM EDT

by CT Outdoors -- Sierra Club

Cycling

20s & 30s Great Falls Reservoir, Mount Prospect, Raccoon Hill, Rand's View

20s & 30s Great Falls Reservoir, Mount Prospect, Raccoon Hill, Rand's View

Sat, Jun 13 · 9:30 AM EDT

by Appalachian Mountain Club - Connecticut Chapter (CT AMC)

Ashintully Gardens

Ashintully Gardens

Sun, Jun 7 · 10:00 AM EDT

by Adirondack Hiking Photography Group

Cycle Babble

Cycle Babble

Sat, Jun 13 · 8:30 AM EDT

by Pittsfield MAtch-up

GroupGolfer.com Special for Copake Lake 2026 - Buy Now for $19.

GroupGolfer.com Special for Copake Lake 2026 - Buy Now for $19.

Sun, Jun 7 · 11:30 AM EDT

by Golf and Tennis Serendipity Group

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