Trail Running calendar near Holyoke 2026-2027

Notchview Ultra in Windsor MA runs multiple timed events on a 1.9 mile loop with an on-course aid station, campsite options, and beneficiaries including the Trustees of Reservations and Baypath Humane Society.

The TARC Blue Hills Skyline Trail Run will take place in Canton on Saturday 11 July 2026. You can run 12 kilometers.

A 5.5 mile trail race at Soapstone Mountain featuring six ascents and about 1500 feet of climbing. The route circles the mountain with multiple steep rocky sections, limited aid access, and a field limited to 50 runners due to parking.

An evening cross-country event at Stonington High School on August 5, 2026, featuring a 5K and a Children's 1/2 Mile for ages 10 and under. The course starts and finishes on the track and includes campus streets, trails, grass, and a bridge..

An 8 hour timed track event at Clapp Park on a certified 0.355 mile dirt and cinder loop, featuring chip timing, trackside bottle drop aid, age division awards, a possible virtual option, and proceeds benefitting the AYJ Fund.

The Tarc Summer Classic will take place in Medfield on Saturday 8 August 2026. You can run between 10 and 40 miles.

Lover's Lane in Chester, VT on August 8, 2026 features 6 hour and 12 hour trail running on a 1.8 mile loop with about 280 feet of elevation per loop. The event is fat ass style with basic aid and benefits local recreation and recovery servi..

Discover new trails at the Tappen Brook 5K in Bridgewater, CT. This community event winds through the scenic woodlands of Bridgewater Town Park. All runners receive a participation gift.

Run trails on a 5 km loop for 8 hours at Crandall's Park. It's a potluck celebration with food, raffles, and games. Complete loops to earn tickets for prizes and a commemorative gift.

The Watermelon Wobbler is a 5k trail run/walk/hike through scenic conservation land and a working farm. It features a varied off-road course and supports local agriculture. On-site parking is supplemented by a satellite lot nearby.

A six hour loop ultra at Jug End State Reservation in Egremont, MA on August 22, 2026. Runners complete as many 4.2 mile laps as they wish; a 0.75 mile mini loop is available in the final hour for distance milestones.

This 4-mile trail run in Schenectady Central Park uses a flexible time trial format. All proceeds support addiction recovery services, honoring a personal legacy. A pre race stretching session is included.

The Old Goat Track Club XC Classic is a 5k cross-country race at Waters Farm in Sutton. It features separate men's and women's races and is the opening event for the USATF New England XC Grand Prix. Enjoy a team tent area, awards, and a pos..

Trail races at Thacher State Park on August 23, 2026 offering 10K, 13.1M, 26.2M and 50K on shared looped courses with cupless aid stations and finish medals for the marathon and 50K.

The Run for the Hills - Niantic will take place in Waterford on Saturday 5 September 2026. You can run 5 kilometers.

The TARC Fall Classic will take place in Carlisle on Saturday 5 September 2026. You can run between 10 and 50 miles.

A trail event centered on the 70 mile Shawangunk Ridge near Rosendale NY offering 70 mile, 30 mile, and half marathon divisions. Routes move over cliffs, pine barrens, wetlands and rugged singletrack; the event is unsupported.

Trail race at Macedonia Brook State Park near Kent, Connecticut offering 12K, 25K and 50K on singletrack with technical climbs, descents and a viewpoint on Cobble Mountain. The 25K is part of the Blue Blazed Trail Running Series.

Join the Charlie Stavros Memorial Beach Run on September 15, 2026 in Westerly, Rhode Island, a free 3 mile beach run honoring a beloved local runner. Enjoy a scenic low tide out and back along Westerly Town Beach with friends and family.

The Where the Pavement Ends trail race offers a technical 4.25-mile single loop or an 8-mile double loop through the Hemlock Hills. It's part of the multi-race Trail Mix Series. Both races start and finish at the Lake Windwing ballfields in..