Outdoor activities in Middlebury, Connecticut

Sun, Sep 14 · 8:30 AM EDT

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

Hosted by: Connecticut Active Singles

40 going

Wed, Sep 17 · 10:30 AM EDT

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

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

Hosted by: The Hiking Group - CT & NY

36 going

Mon, Sep 22 · 10:30 AM EDT

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

Hop Brook Lake, 5-mile hike.

Hosted by: The Hiking Group - CT & NY

27 going

Sun, Sep 21 · 8:30 AM EDT

Sleeping Giant - Hamden

Hosted by: Connecticut Active Singles

49 going

Walking

Sat, Sep 20 · 10:00 AM EDT

September Mindfulness Nature Walk

Hosted by: Women's Mindfulness Nature Walks

3 going

From $20.00

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

Hosted by: The New Haven Collective

Fri, Sep 19 · 10:15 AM EDT

Mon, Sep 29 · 10:30 AM EDT

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

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

Sun, Sep 14 · 8:30 AM EDT

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

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

Hosted by: Connecticut Active Singles

40 going

Running

Mon, Sep 22 · 10:30 AM EDT

Hop Brook Lake, 5-mile hike.

Hosted by: The Hiking Group - CT & NY

27 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 14 · 8:30 AM EDT

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

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

Hosted by: Connecticut Active Singles

40 going

Tue, Sep 30 · 9:30 AM EDT

Paugussett Trail, Webb Mt. to Indian Wells Falls +/- 10 miles, Advanced Hike

Hosted by: CT Outdoors -- Sierra Club

Paugussett Trail, Webb Mt. to Indian Wells Falls +/- 10 miles, Advanced Hike

Cycling

Sat, Sep 27 · 10:00 AM EDT

Family Friendly Hike to Castle Craig

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

Sun, Sep 14 · 1:00 PM EDT

Arrive 12:30 Sunday: Scenic Farmington Bike Ride

Hosted by: Casual Bikers

7 going

Sun, Sep 21 · 4:00 PM EDT

Arrive 12:30 Sunday: Scenic Farmington Bike Ride

Pickleball !!!

Hosted by: Exploring Connecticut (20's, 30's, 40's)

20 going

Sun, Oct 5 · 10:30 AM EDT

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

Suggested groups