Trail Running calendar near Milton 2026-2027

A 50K at Saskadena Six in South Pomfret VT featuring about 27 miles of hilly dirt roads, 3,726 feet of elevation gain, two full aid stations and an 8 hour cutoff; the 2026 race returns after a two year hiatus.

Celebrate spring in the Adirondacks with a scenic half marathon or a family friendly 5k trail race. Support local healthcare while following a historic route from Keene Valley to Elizabethtown.

The Mucker offers a choice of trail adventures in Hubbard Park, from a 5k hike or ruck to a 5k or 5-mile run. It's part of the Montpelier Mudfest weekend. A kids' obstacle course event runs concurrently on the State House lawn.

A memorial trail run at Catamount Outdoor Family Center in Williston, VT on May 2, 2026, with a 3-mile in-person race and a weekend virtual option; the event is free and donations to a memorial fund are encouraged.

This 6-mile mountain race tackles steep trails and muddy terrain at Cochran's Ski Area. After the run, enjoy pancakes and watch the free kids' race. It's the opener for the USATF-New England Mountain Running Series.

Experience the original Spartan Trail Race through the steep climbs and winding trails of the Green Mountain National Forest. Choose from distances between 10 and 200 miles for a true endurance test in Pittsfield Vermont.

A 5K trail run in Hanover New Hampshire held on Mother’s Day, featuring packed trails, open fields and mellow single track. Pre registration is online only and race day registration is available with different fees by age group.

Join this weekly trail running series at the Catamount Outdoor Family Center featuring distances from 5k to 10k. There are special categories for children and water stations available on site for all runners.

Backyard format on May 16, 2026 at Parc régional de l’Île-Lebel: run a collective 6.7 km loop each hour up to 12 laps. Free registration with a suggested donation to the Fondation cancer du sein du Québec.

Join this weekly trail running series at the Catamount Outdoor Family Center featuring distances from 5k to 10k. There are special categories for children and water stations available on site for all runners.

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.

BougeBouge Frederic-Back takes place May 24, 2026 at Parc Frédéric-Back in Montréal, offering trail certified distances from 1 km to 21.1 km. The event features sportstats timing, limited aid stations, restroom facilities, and eco measures.

Join this weekly trail running series at the Catamount Outdoor Family Center featuring distances from 5k to 10k. There are special categories for children and water stations available on site for all runners.

Trail races in Westmore, Vermont on May 30, 2026 include a half marathon, 10 miler and two 5k options over dirt roads and private trails, with a farm to table meal, live music and an evening barn dance.

Join this weekly trail running series at the Catamount Outdoor Family Center featuring distances from 5k to 10k. There are special categories for children and water stations available on site for all runners.

A trail event on Wrights Mountain in Bradford, Vermont on June 6, 2026, with a 5K summit climb and a 1.5 mile fun run for ages 13 and under. Proceeds support the Friends of Wrights Mountain Fund.

Experience trail running at its best in the scenic Parc national du Mont Saint Bruno. Choose from distances ranging from 1 km to 15 km on car free paths surrounded by lakes and forests near Montreal.

The Catamount Weekly Trail Running Race will take place in Williston on Tuesday 9 June 2026. You can run 5 kilometers.

Experience a 6.9 mile mountain race at Cannon Mountain featuring 3,080 feet of elevation gain. Run through technical ski trails and rocky ridges to reach a 4,031 foot summit with views of Franconia Notch State Park.

Ultra Obscura is a six-loop trail event at Mont Sutton that offers multiple distances, technical terrain, and a format focused on strategy and sustainability. Entries are limited to 200 participants.