Trail Running calendar near Rupert 2025-2026

The Slate Valley Scramble, organized by Slate Valley Trails, is a trail running event taking place on August 9, 2025. Participants can choose between an 8k and a half marathon, both set on scenic singletrack and double-track trails in Vermont's Slate Valley. A Kid's Fun Run is also available for chi..

Lover's Lane in Chester, Vermont, is a unique 6- or 12-hour timed running event held on a challenging 1.8-mile loop featuring 280 feet of elevation gain and loss. The course combines single-track, double-track, and jeep trails, offering a fun and engaging experience for runners of all levels. The ev..

The Sweltering Summer Ultra is an annual running event held at Clapp Park in Pittsfield, Massachusetts. The 13th edition features an 8-hour race on a certified 0.355-mile dirt and cinder track, with runners switching directions halfway through. Participants can run or walk as many laps as they choos..

The GTA Challenge will take place in Greenfield on Saturday 16 August 2025.

The Aliza Lapierre Fan Club Trail Race, hosted by the Richmond Trail Running Club in Vermont, is a volunteer-run charity event promoting community and outdoor exploration. The race offers two challenging distances: a 50k and a 26k, both featuring rugged trails and road sections across Huntington, St..

The Jug End Loop Ultra, held at Jug End State Reservation in Egremont, Massachusetts, is a challenging 6-hour ultra running event featuring a 4.2-mile loop course through woods, fields, and an apple orchard. Each lap includes approximately 830 feet of elevation change, with equal uphill and downhill..

The Thacher Park Trail Running Festival, established in 2014, takes place at Thacher State Park in Voorheesville, NY. This scenic event offers participants a choice of four race distances: 10K, 13.1M, 26.2M, and 50K, allowing runners to experience the park's beautiful trails. The festival promotes a..

The Triple Dam 10K is a scenic running and walking event held at the Power Dam Recreation Area in Perkinsville, Vermont. The course is a beautiful loop featuring gently rolling terrain on a mix of grassy trails, dirt roads, and single track, primarily on the west side of the Black River and North Sp..

The Mountain Goat Cabin Trail Run will take place in Rupert on Saturday 13 September 2025. You can run 7 miles.

Wilcox Wild is a challenging 50K trail ultra held in the Adirondack Park Wilderness, New York, starting and finishing at Harrisburg Lake. The rugged course features a lollipop route passing through scenic areas including East Stony Creek Trail, Murphy Trail, Willis Lake, and Wilcox Lake, with an ele..

The Pisgah Mountain Trail Races, held in Pisgah State Park, Chesterfield, New Hampshire, feature two trail running distances: 50K and 23K. Organized by the Red Clover Rovers, this event serves as a fundraiser for the New Hampshire Special Olympics, with all profits supporting their mission. The race..

The Paine Mountain Anchor Challenge Trail Race, held in Northfield, Vermont, is a scenic and challenging 6K trail race that starts and finishes at the Norwich Shaw Outdoor Center. The course features a mix of gravel roads, single-track switchback trails, and steep descents, leading runners to the su..

The TAM Trek is an annual trail race and fun run organized by the Middlebury Area Land Trust to support the Trail Around Middlebury (TAM). This scenic 19-mile loop encircles Middlebury, connecting various local landmarks and conserved properties. Participants can choose from multiple race options, i..

The Vermont 50 Ultra Run is an annual endurance event held at Ascutney Outdoors in West Windsor, Vermont, typically on the last weekend of September. Established in 1993, it features a challenging and scenic course through Vermont's landscape. The event offers multiple race options including a 50-mi..

The Flutters and Foliage Endurance Run, held in Cohoes, NY, is an annual fundraising event supporting Flutters of Hope, a nonprofit aiding individuals and families affected by eating disorders. The race features multiple endurance challenges, including 1-hour, 3-hour, and 6-hour runs, with options f..

Amy’s Adventure Race for the Lake is an annual trail running event held in Bolton Landing, New York, organized by the Lake George Land Conservancy. The race features two challenging courses: a 4.5-mile and a 10-mile route, both winding through scenic forests and rugged single-track trails with rewar..

The Buck 50 is a challenging 50-kilometer ultramarathon held in Kattskill Bay, NY, along the scenic southern Adirondacks near Lake George. The course features rugged, remote trails that traverse four of Lake George's tallest peaks, including Buck Mountain, Sleeping Beauty, Black Mountain, and Erebus..

Devil's Den Ultra is a challenging trail running event held in Bradford, Vermont, featuring a rugged 10K loop on Wright's Mountain. The course offers a mix of terrain, from runnable sections to steep, rocky, and root-filled trails, including a climb to the mountain peak and a wooded downhill. Runner..

The Midstate Massive Ultra Trail is a challenging point-to-point ultra running event held in New Ipswich, New Hampshire, traversing the Appalachian Midstate Trail through central Massachusetts and crossing into New Hampshire, Rhode Island, and Connecticut. Scheduled for October 11-12, 2025, the race..

The Mt. Tom Trail Race is an exciting running event set against the stunning backdrop of Mt. Tom, featuring challenging terrain and breathtaking views, particularly during peak foliage.Participants can choose from a solo 25k, a 2-person 25k relay, or a solo 10k. The race supports the Kestrel Land Tr..