Trail Running Calendar Vermont 2026-2027

Join the Millstone Madness Snowshoe Race on Feb 7 in Websterville VT for a scenic 3 mile loop around old granite quarries on single and double track trails. Snowshoes are required; enjoy friendly competition, prizes, warming fire and raffle..

Runamuck 50K is a rugged trail ultramarathon around South Pomfret, Vermont, weaving hilly dirt roads and scenic backcountry. Expect changeable weather and a true test of endurance on this challenging 50K course.

A spring trail race at Cochran's Ski Area in Richmond, VT on May 3, 2026, featuring a *7mi* steep course, timing, pancakes with Running Saps maple syrup, awards and raffle, with proceeds benefiting youth and a local nonprofit.

A series of rugged trail races in Ripton, Vermont from May 21 to 31, 2026 offering distances from 9 miles to 250 miles plus multi‑marathon and ultra challenges. Camping is available for a one time fee; the event is cup free and no refunds.

A summit trail run on Wrights Mountain in Bradford VT features an 850 foot ascent and views from the town's highest point. A 1.5 mile fun run for ages 13 and under follows lower forest trails with a prize for each child finisher.

Trail races of 25K and 50K loop the Trapp Family Lodge trail system near Mount Mansfield in Stowe, VT, with substantial elevation, three aid stations, and a cup free race policy.

Tackle 8.2 miles and 3,010 ft of climbing at the Cirque Series Killington on June 27, 2026, a steep, technical loop that visits three resort peaks and finishes at the K1 Lodge. Expect rocky, grassy trails and a brutal Needle's Eye climb.

Celebrate July Fourth with the Freedom Run in Newport and Derby, a run or walk along gravel paths and wooded trails. Pick a distance up to a half marathon, enjoy post run ice cream and watermelon, and support NAMI Vermont.

Trail race in Goshen, Vermont offering marked 5 km and 10 km courses on trails and gravel roads. The event is cup free, proceeds support the Blueberry Hill Outdoor Center, and camping is available for a fee.

Volunteer-run charity trail race in Richmond VT offering 50k, 26k and a two person relay on rugged mixed terrain with significant climbing. Proceeds support affordable skiing and snowboarding lessons through Cochran's Ski Area non-profit.

Trail race in Goshen, Vermont beginning and ending at Blueberry Hill Inn. It offers 14 and 36 mile mountain single track routes with significant elevation gain, summit views, aid stations and primitive camping.

A trail run and fundraiser in Poultney, Vermont featuring an 8K, a half marathon, and a kids fun run on wooded singletrack and double-track trails, cup-free aid stations, finisher awards, and post-race snacks and a raffle.

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..

A biannual mountain trail race on Mount Mansfield near Stowe, Vermont, covering about 11 miles and 5,000 feet of climbing over technical and exposed trails. Entry is capped at 70 and requires a recent qualifying time.

A scenic *10 km* loop at the Power Dam Recreation Area in Perkinsville, VT, with grassy trails, dirt roads and a calf-deep river crossing secured by a rope and lifeguard. The event benefits Springfield High School Cross Country and finishes..

A community trail race on September 20, 2026 offering a 19 mile course, 10K and youth 10K, a 5K, and a 2 mile fun run around Wright Park in Middlebury, Vermont.

Tackle five Vermont peaks at the Westmore Mountain Challenge on September 26, 2026, a community focused mountain marathon that benefits NorthWoods Stewardship Center. Choose the full marathon or 20 mile trail course and savor rugged single..

The Vermont 50 offers rugged 50 mile mountain bike and ultrarun courses around Mount Ascutney in West Windsor, Vermont. Held each September, it raises funds for Vermont Adaptive Ski and Sports and includes relays, a 50K and kids activities.

Trail event on a 10K loop near Bradford Vermont offering 30 hour, 12 hour and 10K race formats, a 100-runner cap, pre registration the night before, and tarot-themed finish awards.

A trail marathon and half marathon at Trapp Family Lodge in Stowe, Vermont featuring single track, a climb to Round Top Mountain, multiple aid stations, and significant elevation change.