Trail Running calendar near Pittsfield 2025-2026

Trapp Lodge Mountain Marathon is a challenging trail running event held at Trapp Family Lodge in Stowe, Vermont, offering half and full marathon distances. The course blends runnable double-track with rugged single-track, including a scrambling climb to Round Top Mountain for sweeping views of Mount..

Malta 2K, 3K, 5K Trail Race in Malta, New York, is organized by Roundabout Runners Club. The event begins at Luther Forest Athletic Fields near 30 Rocket Way and runs through the well-maintained trails of 100 Acre Woods, featuring wide stone-dust paths and sections of soft ground that immerse runner..

The Hills Are Alive Cross Country Race, now themed as the Ghostly Gallop Trail 5K, is held at Arrowhead Golf Course in Milton, Vermont. The 5K course runs along the scenic Laura’s Tears trail, offering a trail running experience with a festive Halloween atmosphere encouraging participants to wear co..

New Boston, NH hosts The Hamsterwheel, an 11th-year ultrarun along the New Boston Rail Trail by the Piscataquog River. The course is a continuous 4.0-mile loop that is largely flat with one minor speed bump, starting near the Hillsborough County Fairground and turning at Lang’s Station. Runners may..

The Moreau Half is a challenging 14-mile trail race held at Moreau Lake State Park in Gansevoort, NY. Set amidst scenic mountain singletrack, the course features approximately 2,700 feet of elevation gain, making it a demanding run suited for experienced trail runners. The race starts and finishes a..

RutFest (Richmond Ultra Trail Festival) is the Richmond Trail Running Club’s fifth annual weekend trail festival in Williston, Vermont. The 36-hour event at Catamount Outdoor Family Center features two repeatable trail loops of about 3 and 4 miles on the north and south sides of Catamount, offering..

CircumVictory Trail Run takes place at the Victory Hill Trail Club in Victory, Vermont. The featured run is a roughly 17-mile loop on Victory Hill’s famed singletrack, with some road and cart-trail sections and about 1,800 feet of elevation gain. The run shares the course with two MTB races (34 mile..

The Hugs from Vets Trail will take place in Henniker on Sunday 2 November 2025. You can run 10 kilometers.

The Saratoga Stryders Fall Back 5 Mile Trail Race is held annually at Saratoga Spa State Park in Saratoga Springs, NY. This challenging 5-mile course features a mix of hills, ridges, single-track trails, wide paths, paved sections, grassy areas, and even a stair climb near SPAC, offering runners a d..

Mount Ascutney Vertical Backyard, in Brownsville, Vermont, is a Last Person Standing endurance race on Mount Ascutney. Runners ascend and descend the mountain hourly, with two ascent options: a three-lap orange loop up the t-bar path for 403 vertical feet per lap, or a single ascent on the green loo..

Krampuslauf in Lyme, New Hampshire, at the Dartmouth Ski Way, offers 5K, 10K, and a 9‑hour endurance option. Runners begin at the base lodge and tackle Holt’s side for a steep 5K ascent; 10K participants complete Holt’s and then Winslow side before finishing by the lodge. The 9‑hour loop repeats the..

White Lake Ultras takes place at White Lake State Park in Tamworth, New Hampshire. The festival-like endurance weekend offers 6-, 12-, and 24-hour options on a 2-mile single- and double-track loop around forested lakefront trails, with one short section of beach and sidewalk and about 50 feet of ver..

Infinitus 2026 in Ripton, Vermont, organized by The Endurance Society, is a multi-distance endurance festival with races from 9 miles to 551 miles (the 888K). Distances include the 9 Miler, Marathon, 88K, 100 Miler, Deca-Marathon, 250 Mile, Penta-Marathon, and the 888K. The course is documented on A..

The Whiteface Mountain Races, held in Wilmington, NY, offer a challenging mountain running experience with some of the greatest vertical gain and loss per mile in the U.S. The event features multiple race options including a 21K (two loops), 10K (one loop), Vert Junky combo, 4K Ascent, and a 1-mile..

The Goshen Gallop is an annual trail running event held at the Blueberry Hill Outdoor Center in Goshen, Vermont. Celebrating its 48th year in 2026, the race offers 5K and 10K distances over well-marked courses featuring rugged gravel roads and cross-country ski trails within the Moosalamoo National..