Trail Running calendar near Cheshire 2026-2027

Three summer trail races at West Hill Dam in Uxbridge, MA, with well-marked wooded single and double-track courses, limited fields, age-group prizes, and a portion of fees donated to local food pantries.

Test your endurance at Roosevelt Forest on a 2.1 mile loop featuring classic New England terrain. Complete as many laps as you wish over 33 hours or aim for the 100 mile buckle in this intimate 50 runner event.

A 12 hour timed loop event at Brooksvale Park in Hamden, CT on June 27, 2026, using a 4.25 mile loop with 500 feet gain per loop. Options include marathon and 50k loop targets, aid at each loop, and proceeds aid trail maintenance.

A Spartan obstacle weekend at Carter and Stevens Farm in Barre Massachusetts featuring a 5 km Sprint, a 10 km Super, kids races, and an obstacle workshop across mud, woods, and rolling hills.

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 multi-distance trail event at Red Wing Recreation Area on July 5, 2026, featuring a 15k loop used for 15K, 30K, and 60K races with on-course aid stations, GPX course file, and awards for top finishers.

A five-race Monday evening cross country series at Wickham Park in Manchester CT, the 35th edition features roughly 2.4 to 2.6 mile courses, a discounted full-series entry, and proceeds supporting the Manchester High School Shoe Fund.

The Undercliff/Overcliff will take place in Gardiner on Monday 6 July 2026. You can run 5 miles.

Notchview Ultra in Windsor Massachusetts offers multiple timed and distance events on a 1.9 mile loop with an on-course aid station and camping options. Proceeds support the Trustees of Reservations and Baypath Humane Society.

A point to point 5K in East Hampton beginning at the Connecticut Draft Horse Rescue with shuttle transport from Center School. Bib pick-up is at Center School gym and awards are presented by age group after the race.

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.

New for 2026 at Putnam Memorial State Park, The Revolution is a timed trail event run on a 1.776 mile loop that passes Revolutionary War sites. Runners choose 12 hour, 6 hour, or 3 hour formats and carry their own hydration.

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.

A memorial 5K run and walk at Owen Bell Park in Dayville CT that raises funds for a scholarship for Killingly Ag-Ed seniors. The day includes a 5K, a walk, and a kids fun run on off-road paths with possible trip hazards.

A 1 mile out and back on the Farmington Canal Heritage Trail with a crushed gravel surface and hand timing. Held July 19, 2026 in East Granby in two waves with limited parking; proceeds benefit charities.

Two trail-focused races at Beartown State Forest in Great Barrington, MA: a 5-mile loop around Benedict Pond and a roughly 13.5-mile half with significant climbing and technical terrain. The event is cupless with limited parking and shuttle..

Part of the Shawangunk Runners summer series since 1974, the Blueberry Run in Kerhonkson features a 4.1 mile loop around Lake Minnewaska plus shorter kids races, with parking at Minnewaska State Park and no registration fee.

A third annual cross country event in Warwick, NY on July 25, 2026, featuring a mass-start 5k and a non-timed 400 m Kids Dash with finishers ribbons.

A 5.5 mile trail race at Soapstone Mountain with six steep ascents, a cupless water stop, strict parking limits and online registration capped at 50 runners; the course is technical and not recommended for novices.