Trail Running calendar near Milton 2026-2027

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.

Join a scenic 6K snowshoe at Natural Stone Bridge and Caves on Jan 24, 2026, with rugged forest trails, caves and mountain views. Part of the DION WMAC series with timing, prizes and limited loaner snowshoes plus a warming bonfire.

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..

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 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.

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.

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 4th at Whiteface Mountain Resort in Wilmington NY with a summit finish atop alpine slopes and serious elevation gain. Race a 10k, a two loop SkyRace, or the Vertical K, then join informal Sunday group runs.

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..

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.

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..

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.

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..

A timed walking and trekking event on Cannon Mountain in Franconia, NH with 7, 14, 21, and 28 mile loop options across forest, rocky scrambles, and ridgelines. Optional weighted vests are allowed and finishers within 10 hours earn patches o..

Run the rugged Kilkenny Ridge in the White Mountain National Forest with 50 mile, 25 mile or 25K options over remote, scenic summits and huge climbs. The unmarked course requires GPS, mandatory gear and carries limited aid.