Trail Running calendar near Middlebury 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..

Snowshoe races at Moreau Lake State Park on February 28, 2026, with 15K and 4.7 mile single loops plus a kids 1 mile out and back. Snowshoes are mandatory and limited rentals are available on a first come first serve basis.

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.

Run or walk the Ledge Rock Hill Wine Run 5k at Ledge Rock Hill Winery in Lake George on Sunday May 17 2026, a scenic vineyard course welcoming all paces. Enjoy a T shirt, collapsible wine glass and finisher medal while supporting Nik's Wish..

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.

A two lap mountain race at Mount Sunapee of about 9.2 miles and roughly 3,250 feet of gain, hosting the 2026 USATF Classic Mountain and Collegiate National Championships with a $30,000 prize purse.

Race the Cirque Series at Cannon Mountain on June 13, 2026, a rugged 6.9 mile climb to the 4,031 foot summit with 3,080 feet of gain. Expect rocky, steep trails and sweeping views on this demanding mountain course.

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.

Mountain races at Whiteface Mountain Ski Resort on July 4, 2026 featuring one- and two-loop alpine courses, a steep Vertical K, and a short Kids Klymber, all on utility roads and alpine slopes with on-course aid stations.

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..

A mountain trail race ascending roughly 6.03 miles to the North Peak summit in Lincoln, New Hampshire. The course gains significant elevation, includes steep ski-slope sections such as Upper Walking Boss, and features two aid stations and p..

A Richmond-area trail running event offering 50K, 26K and a two person relay on mixed road and rugged trails with substantial elevation gain. Proceeds support Cochran's Ski Area youth programs.

UltraTrax Gore Mountain is a forest to summit timed trek in North Creek, NY on July 19, 2026 offering looped distances of 7, 14, 21, and 28 miles. Participants can add a weighted vest, follow well marked mountain trails, and have ten hours..

Celebrate the 10th anniversary Ragged 75 around Lake Sunapee, a three stage trail challenge of about 75 miles with 15,500 ft of climbing, or tackle the one day 50k of roughly 33 miles. Camp by the lake, race rugged trails and push your limi..

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.

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.

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..