Trail Running calendar near Pittsfield 2026-2027

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.

A running event in Granville on May 30, 2026: a relatively flat 5k along the rail trail finishing on the footbridge over the Mettowee, plus a kids 1k. Registration opens March 26; 5k fee $25, kids run free.

A forest trail 5K in Montpelier, VT on May 30, 2026 featuring mostly single track, technical roots and rocks, and about 500 feet of elevation gain. The marked course runs through North Branch trails and is part of the local race series.

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 weekly Thursday evening trail run and mountain bike race series at Mt Van Hoevenberg, held June through August, with age divisions, set distances, weekly raffles and series awards.

A 23 km lollipop trail race in the White Mountain National Forest with about 4,500 feet of gain and a 3,478 foot summit on technical, rocky trails. Mandatory mountain gear is required and participants should have prior hilly trail experienc..

A 12-hour trail event in early June 2026 at Overlook Trailhead near Moreau beach featuring a 3.8-mile loop with a steep staircase climb. Participants can run solo, form relay teams, or enter a Fun Run of one to three laps.

A trail event on Wright's Mountain in Bradford, Vermont offering a 5K with an 850 foot climb and a 1.5 mile youth fun run. Proceeds support the Friends of Wrights Mountain Fund for forest maintenance.

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.

A two-lap mountain race at Mount Sunapee Resort on June 7, 2026, covering about 9.3 miles and 3,300 feet of climbing. The event hosts the 2026 USATF Mountain Running Championships and the Collegiate Mountain Running Nationals with cash priz..

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.

A 6.9 miles mountain trail race at Cannon Mountain, New Hampshire with 3,080 ft of elevation gain and a summit at 4,031 feet. The route features a 2 mile Kinsman Ridge section on steep technical trails and a strict 2 hour summit cutoff.

A five mile fun run along the Cheshire Rail Trail from Fitzwilliam Depot to the restored Troy Depot on June 13, 2026. The day features food and festivities, a children's loop, return transport on request, and benefits local historical socie..

A trail race in the Newport town forest with 6- and 3-mile options on rocky, rooty, hilly singletrack. Starts and finishes at Newport High School; proceeds support local recreation and town forest trails.

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.

A weekly trail running series at Catamount Outdoor Family Center in Williston offering 5 km and 2.5 km options, rain or shine, with published per-night fees, a thunder delay policy, weekly bibs, and on-site water refill.

Catamount Ultra at Trapp Family Lodge near Stowe, VT offers 25k and 50k trail loops around Mount Mansfield with aid stations, a cup-free policy, substantial elevation, and a 9 hour limit for the 50k.

Trail races at Dublin School Outdoor Center on June 20, 2026 feature a 10K and a half marathon with significant elevation gain, technical trail sections, and views of Mount Monadnock.

Mansfield Uphill is a 1.7-mile uphill race at Stowe Mountain Resort on June 21 and October 18, 2026, with proceeds supporting the Mansfield Nordic Pro Team. The field is limited, prizes are awarded at Midway Lodge, and a team Q&A follows.

Five Monday evening 5K trail races at Town of Wilton Camp Saratoga across June to August 2026. Entries available per race or as a series package; proceeds benefit the Wilton Wildlife Preserve & Park.