Trail Running calendar near Cheshire 2026-2027

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 looped endurance event at Brooksvale Park in Hamden CT. Runners complete 3.1 mile loops with about 300 feet of gain and aid at each loop, with proceeds supporting local trail maintenance.

A weekend of Spartan obstacle races at Carter and Stevens Farm in Barre MA featuring a 5 km Sprint with 20 obstacles and a 10 km Super with 25 obstacles. The program also includes a kids race and an obstacle workshop.

A 3.1 miles moonlight trail run at Lakeside Park in Pawling, NY with varied terrain, glow markers, required personal light, post run towel and a handmade finisher medal. Proceeds support 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 15K, 30K, and 60K options across a 15k loop with mixed terrain, on-course aid stations, post-race food, 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.

Part of the Shawangunk Runners summer series, this week features a 4.7 mile Undercliff Overcliff loop plus kid races, held at Trapps Bridge with parking at Mohonk Preserve West Trapps and no registration fee.

Notchview Ultra is a multi day running event July 10-13, 2026 in Windsor, MA featuring fixed distance and timed races on a 1.9 mile loop with an aid station, camping logistics, and charity fundraising.

A point-to-point 5K run starting at the Connecticut Draft Horse Rescue and finishing at the Old Home Days grounds, featuring a shaded two-mile section on the Air Line Trail, shuttle transport to the start, evening bib pickup, and pre-regist..

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.

Soapstone Assault is a 5.5 mile trail race in Somers, CT organized by Shenipsit Striders, featuring six ascents and about 1,500 feet of climbing. The course has steep, rocky sections, limited aid access, and the field is capped at 50 runner..

A trail running event at Ward Pound Ridge Reservation offering 25K, 50K and 50M courses across wooded singletrack and carriage roads with runnable sections, ridge views, aid stations, and GPX course files.