Trail Running Calendar Vermont 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..

Tam Trek is a trail race in Middlebury, Vermont, organized by the Middlebury Area Land Trust to raise funds for the Trail Around Middlebury (TAM). It features a 19-mile loop plus shorter options: 10K, 5K, and a 2-mile family fun run. All distances start and finish at Wright Park.The 19-mile course t..

The Westmore Mountain Challenge is a one-day trail run in Vermont’s Northeast Kingdom, covering five mountains—Moose, Hor, Pisgah, Haystack and Bald—for a total distance of about 26 miles and roughly 6,100 feet of elevation gain. The course traverses public trails on steep terrain, with a shuttle-as..

The Vermont 50 Ultra Run is part of the Vermont 50 endurance weekend held at Ascutney Outdoors in West Windsor, Vermont. It includes a 50‑mile Ultra Run and a 50K Run, plus related relay options and other activities that showcase a challenging yet scenic Vermont landscape. Runners traverse the hills..

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 North Face Race to the Summit is a mountain-top running event held at Stratton Mountain in Stratton, Vermont. The course covers about 2.18 miles with a 2,003-foot vertical climb, delivering a steep uphill challenge amid alpine terrain. The race is timed with live results and leaderboards, with o..

The Trapp Lodge Mountain Marathon takes place at Trapp Family Lodge in Stowe, Vermont on October 18, 2025. The event offers two distances: Full Marathon - 26.2 miles (two 13.1-mile laps) Half Marathon - 13.1-mile loop Entry fees vary by date, with early, regular, and day-of pricing for both dista..

The Hills Are Alive Cross Country Race, now themed as the Ghostly Gallop Trail 5K, is held at Arrowhead Golf Course in Milton, Vermont. The 5K course runs along the scenic Laura’s Tears trail, offering a trail running experience with a festive Halloween atmosphere encouraging participants to wear co..

CircumVictory Trail Run takes place at the Victory Hill Trail Club in Victory, Vermont. The featured run is a roughly 17-mile loop on Victory Hill’s famed singletrack, with some road and cart-trail sections and about 1,800 feet of elevation gain. The run shares the course with two MTB races (34 mile..

RutFest (Richmond Ultra Trail Festival) is the Richmond Trail Running Club’s fifth annual weekend trail festival in Williston, Vermont. The 36-hour event at Catamount Outdoor Family Center features two repeatable trail loops of about 3 and 4 miles on the north and south sides of Catamount, offering..

Mount Ascutney Vertical Backyard, in Brownsville, Vermont, is a Last Person Standing endurance race on Mount Ascutney. Runners ascend and descend the mountain hourly, with two ascent options: a three-lap orange loop up the t-bar path for 403 vertical feet per lap, or a single ascent on the green loo..

The Jeff RUN sonville Turkey Trot is scheduled for Thursday, November 27, 2025, in Jeffersonville, VT 05464. The event is organized by the Jeff RUN sonville Run Club and is described as the inaugural running of this town turkey trot. The race site is listed at 201-37 Cambridge Junction Rd. Distance..

Infinitus 2026 in Ripton, Vermont, organized by The Endurance Society, is a multi-distance endurance festival with races from 9 miles to 551 miles (the 888K). Distances include the 9 Miler, Marathon, 88K, 100 Miler, Deca-Marathon, 250 Mile, Penta-Marathon, and the 888K. The course is documented on A..

The Goshen Gallop is an annual trail running event held at the Blueberry Hill Outdoor Center in Goshen, Vermont. Celebrating its 48th year in 2026, the race offers 5K and 10K distances over well-marked courses featuring rugged gravel roads and cross-country ski trails within the Moosalamoo National..