Trail Running calendar near Milton 2025-2026

Celebrate New Year’s Eve with a scenic, untimed run or walk along the Burlington bike path with 1 mile, 5K, or 5 mile out and back options. Gather by the ECHO Leahy Center, then enjoy live music, the burning of Champ and fireworks.

Join Cock a Doodle Shoe on January 18, 2026 at New Land Trust in Saranac NY for a snowy day of fun and fundraising on snowshoes. Tackle a 5K or 10K or bring kids to the free 1/2 mile scramble.

Run through Montreal's famous underground city with a timed indoor 5 km, plus a 5 km walk and 1 km option. Wave starts, on course stairs, and a lively finish at Complexe Desjardins make for a unique winter race experience.

Take on winter trails at Défi des Collines Enneigé in Sainte-Catherine-de-Hatley on Saturday 21 February, with distances from 5.5 km to 30 km perfect for spring marathon prep. Finish to a medal, post race meal and a friendly community atmos..

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 multi day endurance event in Ripton, Vermont from May 21 to 30, 2026, with races from 9 miles to 551 miles for novice to elite ultra runners. Held at Silver Towers near Green Mountain National Forest, camping and dorm lodging..

Join BougeBouge Frederic Back on 24 May 2026 at Parc Frédéric Back in Montréal for certified trail races from 1 km to 21.1 km, perfect for beginners and seasoned trail runners. Enjoy timing, aid stations and a festive finish with medals.

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.

Tackle the scenic Catamount Ultra at Trapp Family Lodge in Stowe, VT with a 25k route or a two lap 50k that winds through highland pastures and hardwood forest by Mount Mansfield. Expect big climbs, sweeping views, helpful aid stations, and..

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 4th at the Whiteface Mountain Races with options from a steep Vertical K to 10k and 20k mountain loops, plus a kids ascent. Finish at the summit and ride the gondola down for unforgettable views and bragging rights.

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.

Run through the Moosalamoo National Recreation Area at the Goshen Gallop, a friendly trail event offering 10K and 5K routes across ski trails and gravel roads. Support local trail stewardship while enjoying a scenic Vermont race.

Join the community at BougeBouge Beaconsfield in Centennial Park for a fun multisport run along a scenic mostly grass 1 km loop offering 1, 2 and 5 km options. Enjoy waterfront views, prizes, medals and refreshments.

Join UltraTrax Gore Mountain on July 19 for a 7 mile loop or multiple loops through shaded Adirondack woods, creeks and ski trail views. Timed trek with weighted options, finisher swag and proceeds supporting Conservation Lands Foundation.

Run single track up to Mount Moosalamoo with lake views at the Moosalamoo Ultra in Goshen Vermont on August 1, 2026. Choose 14 miles with 2400 feet climb or 36 miles with 5000 plus feet for a rugged Green Mountain challenge.

XTERRA Bromont returns Aug 22 to 23 2026 with off road triathlons, gravel races, duathlons and trail runs at Lake Bromont and the Olympic Equestrian Park. Challenging courses, youth events and 28 qualifying slots for XTERRA Worlds make it a..

Trek Cannon Mountain in Franconia New Hampshire and choose 7, 14, 21 or 28 mile routes with ten hours to finish. Rugged trails, sweeping White Mountain views, camaraderie and a post trek gathering with proceeds benefiting conservation.

Take on Kilkenny Ridge in the White Mountain National Forest with 50 mile, 25 mile or 25K options across remote summits and serious climbs. The course is largely unmarked so you must navigate by GPS and carry required safety gear.

Run five Northeast Kingdom peaks in the Westmore Mountain Challenge, a mountain marathon through peak fall foliage on scenic trails. All proceeds benefit NorthWoods Stewardship Center and local trail conservation.