Trail Running calendar near Roxbury 2026-2027

A community fundraising 5K on Legacy Park's cross country trails with professional timing, post-run food and local beer and wine tasting for registrants 21 and over.

A three day 75 mile stage race around Lake Sunapee and a 50K on the SRKG Greenway featuring technical trails, significant elevation gain, and organized overnight camping.

Trail races of 14 and 36 miles around Mount Moosalamoo from Blueberry Hill Inn, featuring mountain single track, significant elevation gain, aid stations and primitive camping.

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 12 km trail race in Hanover NH across Storrs Pond, Oak Hill and Trescott trail systems, featuring single-track, woods roads and cross-country trails.

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 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.

Trail Animals Running Club holds 10M, 50K and 40M trail races on a mostly forested 10-mile loop at Noon Hill Reservation in Medfield MA.

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.

Timed 6 hour and 12 hour loop races in Chester, Vermont on mixed single and double track trails with basic aid and town park amenities.

The 15th Annual 5k Race to the Ledges in Concord, NH on August 8, 2026 features a short road and trail course and includes post-race brunch boxes to take away. Registration includes an adult 5 km entry and a free kids 5 km for ages 6 and un..

A community 5 km run in Derry, New Hampshire on August 8, 2026, with adult and kids categories and online registration closing August 7, 2026.

Trail races at Okemo's Jackson Gore area feature a 7.6 mile summit course with 2500 vertical feet plus short family fun runs, post-race lunch and awards.

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

Multi-distance mountain trail event near Waterville Valley offering 108 mile, 58 mile and 20 mile courses across the White Mountain National Forest with significant elevation gain.

The Beast Coast Sturgeon Run will take place in Winchendon from Friday 14 August 2026 to Sunday 16 August 2026.

A free 8-hour trail event in Tolland, CT where runners complete as many 3-mile loops on a marked 5K-ish course as they like, with provided food and a potluck.

A 5K off-road trail run, walk, and hike at White Barn Farm through Wrentham conservation land. The event is part of the Farm to Trail 5K Series and raises funds to support local agriculture and food pantry donations.

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.