Trail Running calendar near Windsor 2026-2027

A five‑race 5K trail series at Camp Saratoga across summer Mondays, capped at 375 entries for the series. Individual races or a full series package are available and proceeds benefit the Wilton Wildlife Preserve & Park.

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.

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.

A roughly 4.5 mile trail run in Webb Forest near Sunapee, New Hampshire on June 28, 2026, benefiting the Sunapee Middle High School Track and Field program. The course features mountain vistas, single track and varied terrain, with raffle p..

Fourth annual July 4 event in Springfield VT with a 7.4K run and 4K walk along the Black River. Individual fee $20 and a $50 family entry for up to four people; in-person family pricing required.

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.

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.

Trail relay at Ascutney Outdoor Center in Brownsville, VT on July 10-11, 2026 featuring 118 miles of single track, switchbacks and riverside trails; team options include Standard, Ultra and Black Loop with camping and glamping available.

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.

A 5K obstacle mud run in Albany on July 12, 2026 at Harley Rendezvous Classic Inc. The event offers standard and VIP ticket options with race items, rinse stations, and photos, and donates to the National Breast Cancer Foundation.

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.

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 30 km singletrack mountain race in the Catskills on July 26, 2026 with about 4,800 ft of climb and a six hour cut off. The remote route has limited aid, wave starts, and entry requires qualifying standards.