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

Upper Goose Pond - Appalachian Trail to Goose Pond Rd. & Bàck 11 miles , 1500 ft

Upper Goose Pond - Appalachian Trail to Goose Pond Rd. & Bàck 11 miles , 1500 ft

Sat, May 23 · 9:00 AM EDT

by Hiking - Enchantment

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

Racebrook Falls, Sages Ravine, Bear Mountain
- Not for beginners -

Racebrook Falls, Sages Ravine, Bear Mountain - Not for beginners -

Wed, May 20 · 9:30 AM EDT

by CT Outdoors -- Sierra Club

Race Brook Falls, Mt Race to Sages Ravine & Bear Mt

Race Brook Falls, Mt Race to Sages Ravine & Bear Mt

Wed, May 20 · 10:00 AM EDT

by Northeast Hikes with Big Views

Walking

Ashintully Gardens

Ashintully Gardens

Sun, Jun 7 · 10:00 AM EDT

by Adirondack Hiking Photography Group

Upper Goose Pond - Appalachian Trail to Goose Pond Rd. & Bàck 11 miles , 1500 ft

Upper Goose Pond - Appalachian Trail to Goose Pond Rd. & Bàck 11 miles , 1500 ft

Sat, May 23 · 9:00 AM EDT

by Hiking - Enchantment

Nice & Easy Walk

Nice & Easy Walk

Fri, May 22 · 10:00 AM EDT

by Appalachian Mountain Club (AMC) Western MA

Racebrook Falls, Sages Ravine, Bear Mountain
- Not for beginners -

Racebrook Falls, Sages Ravine, Bear Mountain - Not for beginners -

Wed, May 20 · 9:30 AM EDT

by CT Outdoors -- Sierra Club

Running

Racebrook Falls, Sages Ravine, Bear Mountain
- Not for beginners -

Racebrook Falls, Sages Ravine, Bear Mountain - Not for beginners -

Wed, May 20 · 9:30 AM EDT

by CT Outdoors -- Sierra Club

Race Brook Falls, Mt Race to Sages Ravine & Bear Mt

Race Brook Falls, Mt Race to Sages Ravine & Bear Mt

Wed, May 20 · 10:00 AM EDT

by Northeast Hikes with Big Views

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, May 24 · 11:00 AM EDT

by Golf and Tennis Serendipity Group

Cycling

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

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

Sun, May 24 · 11:00 AM EDT

by Golf and Tennis Serendipity Group

Cycle Babble

Cycle Babble

Sat, Jun 13 · 8:30 AM EDT

by Pittsfield MAtch-up

Upper Goose Pond - Appalachian Trail to Goose Pond Rd. & Bàck 11 miles , 1500 ft

Upper Goose Pond - Appalachian Trail to Goose Pond Rd. & Bàck 11 miles , 1500 ft

Sat, May 23 · 9:00 AM EDT

by Hiking - Enchantment

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)

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