Trail Running calendar near West Rock 2026-2027

Experience an empowering 5k obstacle mud run designed for women at Dorothy P. Flint 4-H Camp. Support sisterhood and breast cancer awareness while navigating a fun and muddy course in Riverhead.

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 a historic fire tower is being reconstructed. The event raises funds for Friends of the Fire Tower and Westchester Park..

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.

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.

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

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 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.

A trail event at Red Wing Recreation Area on July 5, 2026 offering 60K, 30K and 15K on a 15k loop with mixed surfaces, aid stations, lap-support for 60K runners, and awards for top finishers.

A point to point 5K in East Hampton that starts at the Connecticut Draft Horse Rescue and finishes at the Old Home Days grounds. Shuttle buses serve the start, pre registration includes a 2026 T shirt and walkers are welcome.

Experience a unique four mile trail race through the historic Forest Park in Queens. Run along naturally carved glacial terrain and pine groves with your dog to support a local animal rescue organization.

Experience a historic trail run at Connecticut's Putnam Memorial State Park. Choose between 3, 6, or 12 hour options on a 1.776 mile loop that passes through former Revolutionary War encampments.

Experience a midweek evening trail run through the diverse terrain of Bowdoin Park. This 5 mile race features a mix of grass and rocky trails with awards for top finishers and a food drive for the local pantry.

Join a community trail run or walk at Owen Bell Park to support the Ryan French Memorial Scholarship Fund. This family friendly event features a 5K trail, a walk, and a free kids fun run.

A one-mile out-and-back on the Farmington Canal Heritage Trail in East Granby, offered in two waves and hand timed, on crushed gravel. Limited parking and a $25 registration fee; all proceeds benefit charities.

Test your endurance at Soapstone Mountain with a five point five mile circuit featuring six mountain ascents. Run through rocky trails and finish at the mountain tower in Shenipsit State Forest.