Skip to content

Outdoor activitiesin Cheshire, Connecticut

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

Hiking

RESCHEDULED 9-14-2025 - Black Rock State Park - Watertown

Hosted by:聽Connecticut Active Singles

46 going
Free
RESCHEDULED 9-14-2025 - Black Rock State Park - Watertown

Roaring Brook - Cheshire

Hosted by:聽Connecticut Active Singles

25 going
Free
Roaring Brook - Cheshire

Indian Well State Park and Birchbank Mtn, Shelton, CT - B Hike - 5-1/2 Miles

Hosted by:聽The Hiking Group - CT & NY

34 going
Free
Indian Well State Park and Birchbank Mtn, Shelton, CT - B Hike - 5-1/2 Miles

Sleeping Giant - Hamden

Hosted by:聽Connecticut Active Singles

48 going
Free
Sleeping Giant - Hamden

Running

Central Valley Square Dance Club FREE fun night

Hosted by:聽Central Connecticut Square Dance Clubs

1 going
Free
Central Valley Square Dance Club FREE fun night

Hop Brook Lake, 5-mile hike.

Hosted by:聽The Hiking Group - CT & NY

27 going
Free
Hop Brook Lake, 5-mile hike.

Hubbard Park: Three Peaks, +/-12 miles, Advanced Intermediate Hike

Hosted by:聽CT Outdoors -- Sierra Club

1 going
Free
Hubbard Park: Three Peaks, +/-12 miles, Advanced Intermediate Hike

Sleeping Giant - Hamden

Hosted by:聽Connecticut Active Singles

48 going
Free
Sleeping Giant - Hamden

Cycling

Arrive 12:30 Sunday: Scenic Farmington Bike Ride

Hosted by:聽Casual Bikers

6 going
Free
Arrive 12:30 Sunday: Scenic Farmington Bike Ride

Cycle Harlem Valley Rail to Trail, Amenia to Copake Falls, NY

Hosted by:聽Appalachian Mountain Club - Connecticut Chapter (CT AMC)

1 going
Free
Cycle Harlem Valley Rail to Trail, Amenia to Copake Falls, NY

West Rim, Castle Craig & Merimere Reservoir Lookout

Hosted by:聽The Hiking Group - CT & NY

28 going
Free
West Rim, Castle Craig & Merimere Reservoir Lookout

Get your bicycle tune up now 馃憤馃徎

Hosted by:聽Scenic Casual Bikers

7 going
Free
Get your bicycle tune up now 馃憤馃徎