Trail Running calendar near Cheshire 2026-2027

A trail 5K in Shirley Chisholm State Park, Brooklyn on June 7, 2026, organized by Black Men Run NYC. Registration is free with an optional $25 singlet; registration opens March 31 and closes June 4.

Trail races at Ward Pound Ridge Reservation on June 7, 2026 include a half marathon and a 10K that pass the summit where the historic fire tower is being reconstructed. Proceeds support the Friends of the Fire Tower within the Westchester P..

Experience a day of trail running and mountain biking at the Norbrook Farm Brewery Trail Festival. Enjoy multiple race distances, local food trucks, and rewards at this scenic Connecticut brewery.

Experience a 5K trail and obstacle run featuring 24 challenges across a 400 acre campus in Wallingford. This inclusive community event supports adaptive sports programs through a mix of wooded trails and open fields.

Experience a scenic evening run on a flat paved loop around Rockland Lake. This chip timed half marathon features sunset views, frequent aid stations, and custom finisher medals only 45 minutes north of NYC.

A six hour timed trail run at Ansonia Nature Center in Connecticut, raced on repeated 1.9 mile counterclockwise singletrack loops with about 170 feet of climb per loop. Entry is limited to 69 runners and refunds are not offered.

Trail race options of 50k, 30k and 10k around Edge Hill Conservation Area in Ashfield Massachusetts, run on single track and dirt roads. The event partners with Franklin Land Trust and supports habitat restoration and land conservation.

An elimination-style loop race near Big River Management Area in West Greenwich, RI. Runners must finish each loop in under 60 minutes to continue; laps repeat until one athlete completes one more loop than the next finisher.

The Turf Wars will take place in New York on Saturday 13 June 2026.

Trail races at Mansfield Hollow State Park include a roughly 15.7 mile out and back on the Nipmuck Trail and a new 5K single track loop; proceeds benefit Connecticut trail stewardship and the event is organized by the Shenipsit Striders.

A community 5K trail run, walk and hike in Eisenhower Park Milford on June 7, 2026 supporting the Milford Rotary and the Beth El Center. The course uses a high school cross country route with mostly flat sections and some rolling hills.

Celebrate the switch to summer with a trail race through the landscape of Hebron Connecticut. Choose between three different distances for a run through the woods during the solstice.

Test your endurance at Elka Park with this 14.5 mile weighted event. Participants navigate over 5,000 feet of elevation gain while carrying a 20 pound pack through the New York landscape.

The Jade's Belmont Plateau 5K will take place in New York on Saturday 20 June 2026. You can run 5 kilometers.

A three-race summer trail series at West Hill Dam featuring well-marked wooded single and double-track trails, limited fields, age-group prizes, and a portion of fees donated to local food pantries.

A lap-based 100-mile trail event at Roosevelt Forest in Stratford, CT, with a 33-hour cutoff and a field limited to 50 runners. The course features New England single and double track, a single pavilion aid station, and pacer rules.

A 12 hour timed event at Brooksvale Park in Hamden CT on a 4.25 mile loop with 500 feet of gain per loop. Multiple-loop options cover marathon and 50k distances and an aid station is available each loop.

Experience an obstacle course weekend at a lush Massachusetts farm featuring rolling hills and mud. Choose from 5k and 10k races or the kids division with onsite farm treats and a local brewery.

A night 5K at Lakeside Park with mixed trail terrain, reflective markers, and required personal lighting; finishes receive handmade medals and proceeds benefit the Pawling Recreation Department.

Experience a unique trail race through the Westmoreland Sanctuary where you choose your own path at the fork. Start and finish at Fox Lane High School for a memorable 5k adventure in Bedford.