Trail Running calendar near Pittsfield 2025-2026

Amy’s Adventure Race for the Lake is an annual trail running event held at Amy's Park in Bolton Landing, New York, within the Adirondacks. The race offers two challenging courses: a 4.5-mile trail and a 10-mile loop, featuring rugged terrain with 700 feet of elevation gain through forests, ponds, an..

The Buck 50 is a challenging 50-kilometer ultramarathon held in Kattskill Bay, New York, along the scenic southern Adirondacks near Lake George. The course features rugged, remote trails that traverse four of Lake George's tallest peaks, including Buck Mountain, Sleeping Beauty, Black Mountain, and..

Devil's Den Ultra is a challenging trail running event held in Bradford, Vermont, featuring a rugged 10K loop on Wright's Mountain. The course offers a mix of terrain, including steep climbs, rocky and rooty sections, and a scenic downhill through the woods. Runners can choose from three race option..

The Trapp Lodge Mountain Marathon is a challenging trail running event held at the scenic Trapp Family Lodge in Stowe, Vermont, nestled in the Green Mountains. Offering both half and full marathon distances, the race features a 13.1-mile loop with approximately 1,900 feet of elevation gain and loss..

The Malta Trail Race in Malta, NY, hosted by the Roundabout Runners Club, offers 2k, 3k, and 5k trail running events set in the scenic 100 Acre Woods. The course starts at the Luther Forest Athletic Fields and features well-maintained trails, mostly covered in stone dust and about six feet wide, wit..

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..

The Hamsterwheel in New Boston, NH, is a unique ultrarunning event featuring 6, 12, 24, and 30-hour races, including relay options. The course is a scenic, largely flat 4-mile loop starting near the Hillsborough County Fairground, running along the New Boston Rail Trail by the Piscataquog River to L..

The Moreau Half is a challenging 14-mile trail race held at Moreau Lake State Park in Gansevoort, NY. Taking place on November 1, 2025, the course features approximately 2,700 feet of elevation gain over technical, winding singletrack trails, making it a demanding event suited for experienced trail..

RutFest is an annual 36-hour running and hiking festival held at the Catamount Outdoor Family Center in Williston, Vermont. The event features two scenic trail loops of 3 and 4 miles, offering stunning views of Camel's Hump and Mt. Mansfield.Participants can run or walk these loops repeatedly at the..

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..

The Mount Ascutney Vertical Backyard is a challenging "Last Person Standing" endurance event held in Brownsville, Vermont. Participants repeatedly ascend and descend 1,209 vertical feet each hour, choosing between three laps on a shorter 403-foot t-bar path or one lap on a longer, more demanding 1,2..

The Krampuslauf is a unique running event held in Lyme, New Hampshire, featuring 5K, 10K, and a challenging 9-hour race. Set on the Dartmouth Ski Way, the course includes two distinct 5K loops on Holt’s and Winslow sides of the mountain, starting and finishing near a scenic ski lodge. The 9-hour rac..

Infinitus is a unique endurance event held in Ripton, Vermont, set amidst the scenic Green Mountain National Forest. The race offers a wide range of distances, from 9 miles up to an extreme 888 kilometers (551 miles), including marathons, ultra-marathons, and multi-day challenges like the Deca-Marat..