Trail Running calendar near Milton 2026-2027

A roughly 3 mile snowshoe race on the Millstone Trails in Websterville, VT, with about 400 ft of elevation. Snowshoes are required; the event includes prizes, raffles, an awards ceremony, cutoffs, and warming fires.

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.

A community race day in Elizabethtown, NY featuring a 13.1 mile half marathon, a new 5K trail race, and a kids 5K for ages 10 and under. Proceeds benefit Elizabethtown Community Hospital and local health programs.

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.

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.

Run the scenic Birdland 5K trail race through Montpelier's North Branch Park. The course features rolling singletrack, forested hills, and babbling brooks. It's a cupless race with category prizes and is part of a local race series.

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.

A mountain trail race at Cannon Mountain on June 13, 2026 covering 6.9 miles and 3,080 feet of ascent. The event offers Sport, Expert and Pro divisions, cash and gear prizes, capped entry and a strict two hour summit cutoff.

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.

A mountain trail race at Killington Resort on June 27, 2026 covering 8.2 miles and 3,010 ft of ascent. Event features Sport Expert and Pro categories, prize awards, two aid stations and a strict summit cutoff.

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.

The Harry Corrow Freedom Run will take place in Newport on Saturday 4 July 2026. You can run between 5 and 13 miles.

The Rochester 5K Trail Run/Walk is a 4th of July event on marked forest trails. It starts and finishes at River Brook Park, following a loop with single-track sections and rolling hills.

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.

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.

A July endurance weekend in the southern Green Mountains offering 100-mile and 100-kilometer races, 17,000 feet of climbing, and a concurrent horse race. Proceeds support Vermont Adaptive Ski & Sport.

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.