Trail Running calendar near Middlebury 2026-2027

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.

A trail race in Newport, New Hampshire on June 13, 2026 offering 6 and 3 mile routes through rocky, rooty, hilly forest trails. Proceeds support Newport Recreation and town forest trails and awards are pure New Hampshire maple syrup.

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.

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.

Catamount Ultra in Stowe, Vermont features a 25K loop of wide, hard-packed trail through pastures and hardwood forest and a 50K option covering the loop twice on June 20, 2026.

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 72-hour endurance race in Pittsfield Vermont on June 26-28 2026 combining physical obstacles, navigation, and mental challenges. Tickets for the Death Race require a promo code issued after acceptance by the race director.

A three-stage Hurricane Heat endurance event at Riverside Farm on June 26-27, 2026, offering 4, 12, and 24 hour tiers that together form a full 24-hour challenge; entry is 18+ with 40+ challenges and team registration options.

A 24-hour endurance challenge in Pittsfield, VT, run on repeated *2-mile* loops with 970 feet of elevation gain per loop. Participants compete for most laps or to endure the full day; tickets start at $135.

Experience a mountain run at Killington Resort featuring 3,010 feet of vertical gain over 8.2 miles. Runners summit three peaks and tackle a steep 45 percent grade climb before finishing at the K1 base area.

A fifteenth annual trail run in Webb Forest, Sunapee NH on June 28, 2026, covering about 4.5 miles to benefit the Sunapee Middle High School Track and Field program. The course features scenic single-track trails and a raffle of sponsor pri..

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.

Mountain running at Whiteface Mountain Ski Resort on July 4, 2026. Options include a single loop Mountain Race (~10 km, ~3,900 ft), a two loop SkyRace (~20 km, ~7,800 ft), a Vertical K and a kids climb, finishing at the summit.

A multi-distance July 4 event in Newport, Vermont offering Half Marathon, 10 Mile, 10K, 5K and a 2 Mile trail. Courses run along the waterfront, on the Beebe Spur Bike Path and on Memphremagog Trails with wooded sections.

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.

A run and walk along the Black River in Springfield, VT, offering 7.4K and 4K options to benefit Springfield High School Cross Country. In-person and virtual entries, packet pick-up, refreshments, prizes, and family registration pricing are..

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.

Gather your team for a two day relay through the scenic Vermont countryside. Run flowy single track trails and camp under the stars at the Ascutney Outdoor Center for an unforgettable weekend of adventure.

A trail running event at Blueberry Hill Outdoor Center in Goshen, VT, offering 5 km and 10 km courses on marked trails and gravel roads, with post-race food, a raffle, awards, camping, and proceeds supporting local trail maintenance.

A 5.7 mile loop on mostly dirt roads with a 450 ft climb in the first three miles and a gradual descent, held July 11, 2026 at Rumney Memorial School in Middlesex, VT.