Trail Running calendar near Windsor 2026-2027

A 5.5 mile mountain trail race at Soapstone Mountain in Somers CT organized by Shenipsit Striders. The course features six ascents, steep rocky sections, a field capped at 50 runners, and required online registration.

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.

A 3.1 mile lap race at Chris Lewit Tennis Academy near Manchester, Vermont, held on wooded trails beside the West River. Net proceeds support veterans charities and all racers receive a free T shirt; family activities include river swimming..

A family-friendly 5K mud run on August 1, 2026 at 508 INTL- Adventure Sports Center with obstacles, mud pits, a pre-party, and a post-race festival.

A five mile trail race on the Gurney Lane Trails in Queensbury, NY featuring single track terrain, chip timed results, age group awards, a post race celebration and proceeds benefiting the Under the Woods Foundation.

A 7-mile USATF sanctioned trail race in Barkhamsted, CT on 08/01/2026. Registration runs 05/03/2026 to 07/31/2026 with a $20 fee and no race day registration; results posted online by Greystone Electronics.

A community fundraising day in Groton, MA on August 5, 2026 featuring an 8.4 mile three-person relay, kids single-loop race and Little Lambs mini runs, followed by barbecue and activities, with proceeds to six local charities.

A trail run fundraiser in Poultney, VT featuring a half marathon, an 8K, and a kid's fun run on wooded single-track trails, with proceeds supporting Slate Valley Trails.

Lover's Lane in Chester, VT is a timed 6 or 12 hour loop event on August 8, 2026 featuring a 1.8 mile loop with 280 feet of elevation per loop. The fat ass style event provides basic aid and supports local recreation and recovery organizati..

Trail runs from Okemo's Jackson Gore area climb to the mountain summit and return on dirt roads and single track. Distances include a 7.6 mile 2500 vert race and a family run under one mile; registration includes shirt, lunch, and medal.

A forested 5K through newly developed trails at Bridgewater Town Park in Connecticut, hosted by the Bridgewater Land Trust and the Bridgewater Recreation Commission. Participants receive a race-day gift and top finishers earn awards.

A summit trail race on Stratton Mountain with youth and open distances, prizes, raffle awards, and proceeds supporting the SMST2 professional ski team.

A multi day timed trail event on a Winchendon farm using a roughly two mile loop. Runners choose from six hour day or night, 12 hour, 24 hour, or 48 hour formats under the Sturgeon Moon.

A free eight hour trail event in Tolland on August 15, 2026 where runners complete as many 3 mile loops as they wish. The event includes on-site food, a potluck, and a GPX course map.

Experience a rolling cross country run through the forests and meadows of the Landis Arboretum. This sanctioned 5K race offers views of the Schoharie Valley and access to scenic trails and gardens.

Experience a community trail run through Elm Ridge Park benefiting the Rocky Hill Fire Department and Library. This event features a two loop trail course for adults and a fun medal race for kids.

A 4.61 mile trail race at Moody Park in Claremont NH featuring narrow single track, wet sections and a steep drop and climb at Gravity Cavity. The event is part of the Western NH Trail Running Series and benefits the local parks department.

A chip-timed 5K run/walk at Brimfield Winery on a two-lap grass course with hills, race swag, a wine pour, and age group awards; a one-lap 1.5 mile division is available.

An eight mile trail run on a well-groomed unpaved carriage path beside the Ashokan Reservoir in West Hurley, NY, limited to 100 runners with age-group awards and a commemorative item for early registrants.

A six-hour loop ultra at Jug End State Reservation in Egremont, MA featuring a 4.2 mile course through woods, fields and an apple orchard. Age-group awards and a handmade finisher mug; proceeds benefit Louison House.