Trail Running calendar near Pittsfield 2026-2027

A 50K ultramarathon at Saskadena Six in South Pomfret, VT, featuring about 27 miles of dirt roads, 3,726 feet of climb, variable footing and weather, two main aid stations, a water stop, and an 8-hour cutoff.

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.

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 trail race on Winant Park Trails near downtown Concord with windy singletrack, switchbacks, and nordic type paths. Two distances are offered and proceeds benefit the Ralph Waldo Emerson School for Preschoolers; day of event entry is avail..

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.

The Free Spirit 50K is a scenic ultra on the dirt roads of Leyden, Massachusetts. The route passes historic farms, forests, and a vintage covered bridge, offering a classic New England countryside experience.

The Canterbury Shaker Village XC 5k will take place in Canterbury on Saturday 16 May 2026. You can run 5 kilometers.

Event Overview The Ledge Rock Hill Wine Run 5K takes place at the Ledge Rock Hill Winery in Lake George, New York. The event features a 5K distance, which is open to participants aged 1 to 99. It is a timed race, with professional timing an..

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.

A trail race in Keene NH on May 23, 2026 using a 12.5k loop system with options up to 50K. The unpaved course features technical single track, jeep roads, cupless aid stations, drop bags, and parking at Fuller Elementary.

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.

Test your endurance at the Ascutney Mountain Run in Vermont. This 3.7 mile uphill race climbs 2,300 vertical feet along a paved auto road to a scenic mountain summit finish.

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 23K mountain trail race in Tamworth, New Hampshire, with about 4,800 feet of climbing and a loop over the 3,478 foot summit of Mount Chocorua. The event requires mandatory safety gear and is cupless.

A looped trail event in Moreau, New York in June 2026 built around a steep staircase climb. Runners can race solo, form relay teams with flexible lap order, or join a Fun Run covering one to three laps.

Trail event in Bradford, VT with a 5K that gains 850 ft to Wrights Mountain and a 1.5 mile fun run for youths. Proceeds support the Friends of Wrights Mountain Fund.

Sunapee Scramble on June 7, 2026 is an up and down mountain race at Mount Sunapee that serves as the 2026 USATF National Classic Mountain Championship and features a $30,000 prize purse. The course is about 9.2 miles with 3,250 feet of vert..