Trail Running calendar near Milton 2026-2027

A free trail running event at Catamount Outdoor Family Center with a 3-mile in-person race and a weekend virtual 3-mile option, held in memory of a UVM student and Army ROTC cadet. T-shirt sales support a memorial fund.

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.

Trail event in Pittsfield, Vermont, May 6 to 9, 2026, offering distances from 10 miles to 200 miles through the Green Mountain National Forest. Team entries can secure the same start time and service member discounts are available.

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.

A weekly trail running series at Catamount Outdoor Family Center in Williston, VT offering 2.5 km and 5 km courses plus a Cubbies category for ages 5 and under; races run rain or shine with clear thunder and bib policies.

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.

A weekly trail race series at Catamount Outdoor Family Center in Williston offering 5 km and 2.5 km options, rain or shine, with on-site bib pickup, a thunder delay/cancellation policy, and a water refill station near the bike wash.

Infinitus in Ripton, Vermont runs May 21 to 31, 2026 and offers trail races from a 9 mile option up to 250 mile and multi marathon formats. The course uses two loops and on site camping is available for a small cash fee.

BougeBouge at Parc Frédéric Back on 24 May 2026 offers certified trail distances from 1 km to 21.1 km with limited on site water service and morning bib pick up at the venue.

A weekly trail running series at Catamount Outdoor Family Center in Williston, VT with 5K and Half Lap options, adult and youth categories, weekly bib pickup, rain or shine policy, and on-site water refill and safety check in.

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.

A trail 5K at Montpelier's North Branch Park with rolling singletrack, forested hills, and brooks. The cupless event uses a mass start, has pre registration and day of fees, and awards gift cards to category winners.

Weekly trail races at Catamount Outdoor Family Center in Williston, VT offer 2.5 km, 5 km and 10 km options for adult and youth runners. Events run rain or shine with a clear thunder policy and weekly bib distribution.

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.

An 8 mile uphill road race climbing about 3,500 feet to the summit of Whiteface Mountain, finishing with 360° views of the Adirondacks, New England and Canada. Entry includes a finishers medal and a t-shirt.

Trail event at Parc national du Mont‑Saint‑Bruno offering distances for children and adults, electronic timing, aid stations, participation medal and technical shirt, with bib transfer options and an opportunity to donate to Fondation Charl..

A weekly trail running series at Catamount Outdoor Family Center in Williston VT offering 5K and 2.5 km options, weekly bibs, weather and thunder policies, on site water refill, and check in procedures for safety.

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.

Experience a scenic 14K run over the dirt roads of Jeffersonville and Fletcher. Support local Vermont farmers while enjoying live music, fresh food, and community celebrations following the race.