Trail Running calendar near Middlebury 2025-2026

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 Royal (multi) Mile Hill Run is a challenging 5K race held during the NH Highland Games & Festival in Lincoln, New Hampshire. Scheduled for September 21, 2025, the event features a course with an elevation gain of 800 feet, traversing dirt trails, service roads, and ski trails. Participants recei..

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, offering a 50-mile ultra run and a 50K race. The event i..

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, New York, 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..

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, including steep climbs, rocky and rooty sections, and a scenic downhill through the woods. Runners can choose from three race option..

The Trapp Lodge Mountain Marathon is a challenging trail running event held at the scenic Trapp Family Lodge in Stowe, Vermont, nestled in the Green Mountains. Offering both half and full marathon distances, the race features a 13.1-mile loop with approximately 2/3 double track and dirt roads and 1/..

The Hills Are Alive Cross Country Race is set to take place at Arrowhead Golf Course in Milton, Vermont. This event features a 5K race on the scenic Laura’s Tears trail, welcoming runners aged 12 and older. Participants can pre-register online, with a fee of $15, and GMAA members receive a discount...

The Moreau Half is a challenging 14-mile trail race held at Moreau Lake State Park in Gansevoort, NY. Taking place on November 1, 2025, the course features approximately 2,700 feet of elevation gain over technical, winding singletrack trails, making it a demanding event suited for experienced trail..

RutFest, held in Williston, Vermont, is an inclusive 36-hour ultra trail running and hiking event hosted at the Catamount Outdoor Family Center. Participants run or walk two scenic trail loops, approximately 3 and 4 miles each, featuring beautiful views of Camel's Hump and Mt. Mansfield.The event en..

The Saratoga Stryders Fall Back 5 Mile Trail Race is an exciting running event set in the scenic Saratoga Spa State Park. Participants can enjoy a challenging course that features a mix of hills, ridges, and single-track trails, showcasing the park's natural beauty. The race encourages runners to em..

The Mount Ascutney Vertical Backyard is a challenging "Last Person Standing" endurance event held in Brownsville, Vermont. Participants repeatedly ascend and descend 1,209 vertical feet each hour, choosing between three laps on a shorter 403-foot t-bar path or one lap on a longer, more demanding 1,2..

The Krampuslauf is a unique running event held in Lyme, New Hampshire, featuring 5K, 10K, and a challenging 9-hour race. Set on the Dartmouth Ski Way, the course includes two distinct 5K loops on Holt’s and Winslow sides of the mountain, starting and finishing near a scenic ski lodge. The 9-hour rac..

Infinitus is a unique endurance event held in Ripton, Vermont, offering a range of race distances from 9 miles up to an extreme 551-mile challenge known as the 888k. Set within the scenic Green Mountain National Forest, the course provides a demanding and adventurous experience for participants. The..