Trail Running calendar near Pittsfield 2026-2027

A 50K trail ultramarathon in the Wilcox Lake Wild Forest near Stony Creek, NY, run as a lollipop loop from Harrisburg Lake through East Stony Creek Trail and Wilcox Lake. It includes two aid stations, water filter opportunities, and a post-..

Experience a historic celebration of Scottish heritage at Loon Mountain Resort featuring heavy athletics, stone lifting, and traditional music amidst New Hampshire's scenic fall foliage.

Test your limits at the birthplace of Spartan Race in the Green Mountains of Vermont. Choose from distances ranging from 5km to 50km featuring steep climbs and rugged off trail descents at the iconic Killington Ski Resort.

Experience the scenic Trail Around Middlebury with distances ranging from a 2 mile fun run to a full 19 mile loop. Enjoy single track trails and mountain views in this community event supporting Vermont footpaths.

A mountain trail event near East Charleston, Vermont, crossing five named peaks with timed full marathon and a 20 mile trail-only option. Proceeds support the NorthWoods Stewardship Center and local trail stewardship.

Experience an endurance tradition at Mt. Ascutney featuring 50 mile and 50 km ultra runs, mountain bike races, and team relays. This scenic event supports Vermont Adaptive and includes fun races for kids.

Hit the Trail 2026 offers a timed 5K run/walk or bicycle rides on Vermont's scenic Lamoille Valley Rail Trail. The event raises funds for healthy aging services in Central Vermont. Join the community in Morrisville on September 27 for a day..

Experience a rugged trail race through the Adirondack forests and wetlands of Amy’s Park. Enjoy scenic views and a community after party at a local brewery while supporting land conservation for Lake George.

The Buck 50 is a 50 km ultra that tackles four of Lake George's tallest peaks in the southern Adirondacks. With 9000 ft of climbing on rugged trails, it's a demanding point-to-point loop starting and finishing at Camp Chingachgook. The even..

Experience the seasonal scenery of New Hampshire at the Keene Family YMCA Fall Foliage Trail Race. Choose between a fast 5K or a 10K with elevation gain to support local community programs.

The Mile for Mentoring will take place in Gilford on Sunday 4 October 2026.

An October 10 to 11, 2026 event in Bradford Vermont with 30 hour, 12 hour and 10K formats on a 10 km loop on Wrights Mountain. The race features assigned pit areas, pre race check in, themed Tarot finish tokens and milestone awards.

Trail marathon and half marathon at Trapp Family Lodge in Stowe, VT, run on a 13.1 mile loop with mixed double-track and rugged single-track that reaches Round Top Mountain. The full distance is two loops.

Explore the scenic trails of 100 Acre Woods in Malta, New York. This community event on October 18, 2026 features 2k, 3k, and 5k trail runs. All proceeds support local trail maintenance.

This Halloween-themed 5K trail run takes place on the Laura’s Tears trail at Arrowhead Golf Course. Awards are given to the top finishers, and costumes are encouraged. Refreshments and facilities are available.

Experience a timed mountain trek across the rugged ridges of Vermonts Northeast Kingdom. Choose from multiple loop distances and the option to carry weighted gear for an added challenge on the scenic trails of Burke Mountain.

Tackle a unique mountain course that goes up and down four times over 4.9 miles. The event offers prize money, age group awards, and benefits the Keene Community Kitchen. Early registration includes a t-shirt.

A trail half marathon at Moreau Lake State Park featuring roughly 14 miles and 2700 feet of climbing on technical singletrack, a marked course with one aid station, and park parking near the beach.

A Last Person Standing mountain event in Brownsville, VT where runners repeat hourly climbs totaling large elevation gains. Options include a higher turnaround of about 1,209 feet or repeated t bar repeats; aid and indoor facilities are pro..

Race Mozey brings the Central European Krampus Run tradition to New England. Choose from a 5K, 10K, or a 9-hour challenge to complete laps at the Dartmouth Skiway. Finishers get medals, and the event supports Vermont Adaptive Ski and Sports..