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Outdoor activitiesin Pittsfield, Massachusetts

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

Hiking

Mount Greylock Hike, 8.6 miles with 2,536' elevation

Hosted by: Connecticut Hike Bike and Paddle

24 going
Free
Mount Greylock Hike, 8.6 miles with 2,536' elevation

Upper Goose Pond - Appalachian Trail

Hosted by: Hiking - Enchantment

13 going
Free
Upper Goose Pond - Appalachian Trail

2 Nights Camping and Saturday night at Tanglewood

Hosted by: North Central MA-Southern NH Hiking Group

10 going
Free
2 Nights Camping and Saturday night at Tanglewood

MASS AT Series Part IX; Blotz Road to Furnace Hill/Cheshire, Point to Point

Hosted by: CT Outdoors -- Sierra Club

3 going
Free
MASS AT Series Part IX; Blotz Road to Furnace Hill/Cheshire, Point to Point

Walking

2 Nights Camping and Saturday night at Tanglewood

Hosted by: North Central MA-Southern NH Hiking Group

10 going
Free
2 Nights Camping and Saturday night at Tanglewood

Chesterfield Gorge

Hosted by: West Central Mass Hiking

3 going
Free
Chesterfield Gorge

Walk with us in Rensselaer

Hosted by: Walk for Fun, Fitness and Friendship

3 going
Free
Walk with us in Rensselaer

MASS AT Series Part IX; Blotz Road to Furnace Hill/Cheshire, Point to Point

Hosted by: CT Outdoors -- Sierra Club

3 going
Free
MASS AT Series Part IX; Blotz Road to Furnace Hill/Cheshire, Point to Point

Running

MASS AT Series Part IX; Blotz Road to Furnace Hill/Cheshire, Point to Point

Hosted by: CT Outdoors -- Sierra Club

3 going
Free
MASS AT Series Part IX; Blotz Road to Furnace Hill/Cheshire, Point to Point

MASS AT Series Part X; Cheshire to Saddle, Greylock, Fitch & Williams, P to P

Hosted by: CT Outdoors -- Sierra Club

6 going
Free
MASS AT Series Part X; Cheshire to Saddle, Greylock, Fitch & Williams, P to P

Chesterfield Gorge

Hosted by: West Central Mass Hiking

3 going
Free
Chesterfield Gorge

Mt. Greylock up Bellow Pipe, Adams MA

Hosted by: Hartford Area Hiking™

16 going
Free
Mt. Greylock up Bellow Pipe, Adams MA

Cycling

Chesterfield Gorge

Hosted by: West Central Mass Hiking

3 going
Free
Chesterfield Gorge

BIKEPACKING TRIP: Lake Ontario and Niagara Falls, 6/21 - 6/23

Hosted by: Rochester Bicycling Club (RBC), Rochester NY

6 going
Free
BIKEPACKING TRIP: Lake Ontario and Niagara Falls, 6/21 - 6/23

MASS AT Series Part IX; Blotz Road to Furnace Hill/Cheshire, Point to Point

Hosted by: CT Outdoors -- Sierra Club

3 going
Free
MASS AT Series Part IX; Blotz Road to Furnace Hill/Cheshire, Point to Point

Peebles Island State Park (not paved, but well beaten)

Hosted by: Weekday Daytime mostly paved path Walking Near Albany

11 going
Free
Peebles Island State Park (not paved, but well beaten)