Outdoor activities in Cheshire, Connecticut

Sun, Sep 14 · 8:30 AM EDT

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

Hosted by: Connecticut Active Singles

44 going

Sun, Sep 21 · 8:30 AM EDT

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

Sleeping Giant - Hamden

Hosted by: Connecticut Active Singles

46 going

Roaring Brook - Cheshire

Hosted by: Connecticut Active Singles

Sun, Oct 5 · 9:30 AM EDT

24 going

Mon, Sep 29 · 10:30 AM EDT

Black Rock State Park Watertown, CT - B+ Hike - 5-1/2 to 6-1/2 Miles

Hosted by: The Hiking Group - CT & NY

23 going

Black Rock State Park Watertown, CT - B+ Hike - 5-1/2 to 6-1/2 Miles

Walking

Sat, Sep 20 · 10:00 AM EDT

September Mindfulness Nature Walk

Hosted by: Women's Mindfulness Nature Walks

2 going

From $20.00

North Haven -- Anybody want to take a morning (ish) walk? -- weather permitting

Hosted by: The New Haven Collective

Wed, Sep 10 · 10:15 AM EDT

4 going

Mon, Sep 22 · 10:30 AM EDT

North Haven -- Anybody want to take a morning (ish) walk? -- weather permitting

Hop Brook Lake, 5-mile hike.

Hosted by: The Hiking Group - CT & NY

26 going

Walk

Hosted by: Keep It Moving Walking Group for Women

Tue, Sep 9 · 5:00 PM EDT

Running

Mon, Sep 22 · 10:30 AM EDT

Hop Brook Lake, 5-mile hike.

Hosted by: The Hiking Group - CT & NY

26 going

Thu, Sep 25 · 9:30 AM EDT

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

Hosted by: CT Outdoors -- Sierra Club

Sun, Sep 21 · 8:30 AM EDT

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

Sleeping Giant - Hamden

Hosted by: Connecticut Active Singles

46 going

Thu, Sep 18 · 9:30 AM EDT

Sleeping Giant: All the Red Trails, +/-8 miles, Challenging Hike

Hosted by: CT Outdoors -- Sierra Club

4 going

Sleeping Giant: All the Red Trails, +/-8 miles, Challenging Hike

Cycling

Sun, Sep 14 · 1:00 PM EDT

Arrive 12:30 Sunday: Scenic Farmington Bike Ride

Hosted by: Casual Bikers

Sun, Oct 5 · 10:30 AM EDT

Arrive 12:30 Sunday: Scenic Farmington Bike Ride

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

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

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

New Hampshire Multi Day Gravel Adventure Ride

Hosted by: Farmington Bike Up!

Mon, Sep 8 · 8:00 PM EDT

Fri, Sep 12 · 10:30 AM EDT

New Hampshire Multi Day Gravel Adventure Ride

West Rim, Castle Craig & Merimere Reservoir Lookout

Hosted by: The Hiking Group - CT & NY

22 going

West Rim, Castle Craig & Merimere Reservoir Lookout

Suggested groups