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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

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

Mt. Greylock - Summit Hike (Hopper Trail)

Hosted by: Hiking - Enchantment

16 going
Free
Mt. Greylock - Summit Hike (Hopper Trail)

(Hiking) Mt. Greylock - Hopper Trail (8 Miles)

Hosted by: Pioneer Valley Over 55 Social Circle

4 going
Free
(Hiking) Mt. Greylock - Hopper Trail (8 Miles)

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

Hosted by: Litchfield County Explorers

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

Running

Leisurely Paddle at Cheshire Reservoir

Hosted by: Western Mass (& Beyond) Kayak Group

1 going
Free
Leisurely Paddle at Cheshire Reservoir

MASS AT Series Part XI; Mt. Williams to Vermont Border to Long Trail, P to P

Hosted by: CT Outdoors -- Sierra Club

4 going
Free
MASS AT Series Part XI; Mt. Williams to Vermont Border to Long Trail, P to P

Ice Glen Trail

Hosted by: The New England Hiking Group

1 going
Free
Ice Glen Trail

Sunday bRUNch Run - Cafe Madison

Hosted by: The Most Informal Running Club, Ever (TMIRCE): Upstate

1 going
Free
Sunday bRUNch Run - Cafe Madison

Cycling

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

Hosted by: Connecticut Hike Bike and Paddle

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

Leisurely Paddle at Cheshire Reservoir

Hosted by: Western Mass (& Beyond) Kayak Group

1 going
Free
Leisurely Paddle at Cheshire Reservoir

POSTPONED Albany-Hudson Electric Trail - Valatie

Hosted by: Weekday Daytime mostly paved path Walking Near Albany

4 going
Free
POSTPONED Albany-Hudson Electric Trail - Valatie

Basin Pond

Hosted by: The New England Hiking Group

1 going
Free
Basin Pond