Trail Running calendar near Windsor 2026-2027

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..

Muddy Dash Boston is a family-friendly 5K mud run at 508 INTL Adventure Sports Center on August 1, 2026, with obstacles, mud pits and slides, plus a pre-party and an after-party with music and food.

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.

An eight hour track race at Clapp Park in Pittsfield, MA on a certified .355 mile loop with chip timing, bottle drop aid, age group awards, and proceeds benefiting the AYJ Fund. A virtual option may be available.

Trail run and fundraiser in Poultney Vermont featuring an 8K, a half marathon and a kids fun run on singletrack and double track trails. Cup free aid stations offer refills, with awards, snacks and a post race raffle.

A timed 6 hour and 12 hour loop event in Chester, VT on August 8, 2026. The 1.8 mile loop has about 280 feet of climb per lap and basic aid plus communal food are available.

The 3rd Annual Tappen Brook 5K in Bridgewater, CT on August 9, 2026 runs on the new Bridgewater Town Park trails through woodlands near Lake Lillinonah, with participation gifts and awards for top finishers.

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.

An eight-hour trail event in Tolland, Connecticut where participants run repeated ~5K loops from Crandall's Pavilion. The day includes music, a potluck with pancakes and burgers, and proceeds that support Connecticut trail stewardship.

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.

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 timed 5K at Brimfield Winery on August 15, 2026, run on a mostly grass cross country style course. Registration options include a standard 5K with a postrace wine pour and a volunteer plus run option.

Jug End Loop Ultra on August 22, 2026 at Jug End State Reservation in Egremont, MA features a 4.2 mile loop through woods, fields and an apple orchard. Participants run as many 4.2 mile laps as they choose within six hours and receive award..

A 4 mile open time trial on the single track trails of Schenectady Central Park with individually timed laps. All proceeds go to Hive of Hope, a community organization supporting recovery through connection and movement.

A trail running festival at Thacher State Park on August 23, 2026, offering **10K**, **13.1M**, **26.2M** and **50K** courses that share the same first 10K loop. The cupless event has multiple aid stations, post-race food, and medals for ma..

A 5K cross country race at Waters Farm in Sutton Massachusetts that opens the USATF New England XC Grand Prix series. Separate men's and women's open races, on site registration, and a post race awards ceremony.

An inclusive trail festival at Northfield Mountain on August 29, 2026 that centers queer and trans runners and allies. It offers a 20k prediction race, an untimed 5k fun run or hike, and a Kid's Run with community-focused prizes.

A 10 km race at Power Dam Recreation Area in Perkinsville, VT on August 30, 2026, part of the Western NH Trail Running Series. Online registration closes August 28, 2026; youth entries are free and age-based fees apply.