Trail Running calendar near Wilton 2026-2027

A charity trail event at Trenton Fish and Game Club supporting autism awareness, featuring a 5 Miles trail run, a 5 Miles walk and a supervised 1K kids fun run. Proceeds benefit local organizations including Kelberman.

An eight hour track endurance event at Clapp Park in Pittsfield, MA featuring a certified 0.355 mile loop, chip timing with live leaderboard, on-course bottle drop and age group awards. Proceeds support the AYJ Fund.

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 6 hour or 12 hour fat-ass trail event on a 1.8 mile loop near Chester town park, with 280 feet of climb per loop. Basic aid and food are provided and proceeds benefit local recreation and recovery organizations.

Trail races at Mt Van Hoevenberg on August 8, 2026 offer 10K, half marathon and 50K courses over single track and steep terrain. Start and finish are in the venue stadium and course maps are provided.

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 6 hour timed ultra and a 4.2 mile memorial run at Jug End State Reservation in Egremont MA on August 22, 2026. The loop covers woods and orchards with 830 feet elevation per lap and benefits Louison House and Dana Farber.

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..

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.

A rugged 50K trail ultra in the Wilcox Lake Wild Forest on September 6, 2026, starting and finishing at Harrisburg Lake. The lollipop route includes two aid stations and requires prior experience and a wait list review.

A Keene State College alumni cross-country meet on 09/12/2026 at the Keene State Athletic Complex featuring a men's 5K and a women's 2 Mile race; registration runs 09/06 to 09/12 with a $25 fee per event.

Three events at the Springfield Dam on 09/12/2026 include a kids 0.5 mile, a one-mile Maniac Mile for ages 10+, and a 3.1 mile trail run with views of Mt. Ascutney. Food vendors and family activities are planned.

A trail race day at Pittsfield State Forest with 50k, 25k, 15k and a new 5 mile option, a double-loop course with three aid stations and charity fundraising through BURCS and Free to Run.

Trail races in Pisgah State Park near Chesterfield, New Hampshire offering 50K and 23K distances, organized by the Red Clover Rovers as a fundraiser for the Special Olympics of New Hampshire.

Sep 19-20, 2026 in Killington, VT: Spartan obstacle races across steep, off-trail terrain in the Green Mountains. Events include Sprint 5 km, Beast 21 km, Ultra 50 km and kids races; tickets start from $29.

Trail run and walk at Huyck Preserve in Rensselaerville NY on Saturday September 19 2026. Routes of 2 5 and 8 miles pass Lake Myosotis and a historic racetrack while raising funds for local organizations.

An 8.5 mile loop at Merck Forest with about 1,800 feet of climbing, two aid stations, and a 0.75 mile kids loop around the farm. Packet pick-up is available in Manchester and at the Sap House start area.