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

Taconic Crest Trail (TCT)

Taconic Crest Trail (TCT)

Sat, May 16 · 4:00 AM EDT

by Connecticut Hike Bike and Paddle

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

AT Connecticut to Mass line, Backpack adventure

AT Connecticut to Mass line, Backpack adventure

Sat, May 16 · 9:00 AM EDT

by Hudson Valley Hikers

Walking

AT Connecticut to Mass line, Backpack adventure

AT Connecticut to Mass line, Backpack adventure

Sat, May 16 · 9:00 AM EDT

by Hudson Valley Hikers

Nice & Easy Walk

Nice & Easy Walk

Fri, May 29 · 10:00 AM EDT

by Appalachian Mountain Club (AMC) Western MA

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

Mt. Warner Loop/ Wednesday Evening Walks/hikes

Mt. Warner Loop/ Wednesday Evening Walks/hikes

Wed, May 20 · 6:00 PM EDT

by Appalachian Mountain Club (AMC) Western MA

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

AT Connecticut to Mass line, Backpack adventure

AT Connecticut to Mass line, Backpack adventure

Sat, May 16 · 9:00 AM EDT

by Hudson Valley Hikers

Bread Loaf Mountain to Pine Knob Loop and back.

Bread Loaf Mountain to Pine Knob Loop and back.

Mon, May 25 · 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

Cycling

AT Connecticut to Mass line, Backpack adventure

AT Connecticut to Mass line, Backpack adventure

Sat, May 16 · 9:00 AM EDT

by Hudson Valley Hikers

Harlem Valley Rail Trail 25+- North from Millerton

Harlem Valley Rail Trail 25+- North from Millerton

Sun, May 17 · 11:00 AM EDT

by The Hudson Valley Rail Trail Riders

Cycle Babble

Cycle Babble

Sat, Jun 6 · 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, May 24 · 11:00 AM EDT

by Golf and Tennis Serendipity Group

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