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.

Infinitus is a multiday endurance festival May 21 to 30 in Ripton, Vermont, with distances from 9 miles to 551 miles. Tackle a marathon or join an epic ultrarunning challenge amid scenic Green Mountain forests.

Run scenic loops around Trapp Family Lodge on June 20 in Stowe Vermont with 25K and 50K options. Wide hard packed trails wind through pastures and hardwood forest with well stocked aid stations for a scenic, challenging race.

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.

Tackle scenic trail and gravel road courses through the Moosalamoo area of Green Mountain National Forest with sweeping views from Hogback. Choose 5K or 10K and support the Blueberry Hill Outdoor Center while enjoying a friendly community r..

Run rugged singletrack to Mount Moosalamoo in Goshen Vermont with Lake Dunmore views, choosing 14 mile or 36 mile distances that test your climbing legs. Entry includes a shirt, postrace meal, finishers award and primitive camping.

Run the Triple Dam 10K in Perkinsville VT on a scenic loop of grassy trails, dirt roads and a shallow river crossing. Open to runners and walkers, this fundraiser for Springfield XC finishes by a swimming hole with post race treats.

The Tam Trek will take place in Middlebury on Sunday 20 September 2026. You can run between 5 and 19 miles.

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 is a classic late September mountain bike and ultra run at Mount Ascutney offering 50 mile and 50K options, plus family fun and kids activities on Saturday. Proceeds support Vermont Adaptive Ski and Sports.

Devil's Den Ultra near Bradford VT challenges runners with a rugged 10K loop offering 30 hour, 12 hour and 10K options on rocky, rooty mountain trails. Entries are capped at 100 and registration opens Jan 1 2026.

Join the von Trapp Mountain Marathon in Stowe Vermont with full and half marathon options on a rugged 13.1 mile loop. Steep climbs, a scramble to Round Top and sweeping views of Mount Mansfield create a rewarding mountain trail.

Run the Ghostly Gallop Trail 5K in Milton VT on October 25. This Halloween themed, costume friendly trail race on Laura's Tears at Arrowhead Golf Course offers prizes, post race refreshments, and family friendly fun for ages 12 and up.

UltraTrax Burke Mountain is a timed trekking challenge on scenic trails across Burke Mountain. Choose 7, 14, 21 or 28 miles and finish within 10 hours to earn a shirt, patch and longer distance medals, plus post trek food and activities.