Trail Running calendar near Pittsfield 2025-2026

Amy’s Adventure Race for the Lake, hosted by the Lake George Land Conservancy, takes place at Amy’s Park in Bolton Landing, NY. The event offers two trail options: a 4.5-mile race and a 10-mile loop, featuring rugged single-track through fo..

Michael J. Pitney Farm Run takes place at Pitney Meadows Community Farm in Saratoga Springs, NY. The event features a 5K community run and a Youth Fun Run (.5 miles).The course is a mixed-surface, grass and stone-dust trail that is primaril..

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, in..

Keene Family YMCA Fall Foliage Trail Races in Keene, New Hampshire offer 5K and 10K trail runs starting and finishing at the Keene YMCA (200 Summit Road). The 5K provides a fast, beginner-friendly taste of trail running, while the 10K adds..

Blackhawk Blaze is a trail running event held in Plainfield, New Hampshire (Meriden area), at 92 Bonner Road, near Plainfield School. This sixth annual Plainfield tradition offers two races: a 5K Trail Race on the famed French's Ledges trai..

Event overview Devil's Den Ultra takes place October 11-12, 2025 in Bradford, Vermont, at 1250 Chase Hollow Rd. The event offers these race options: 30-Hour 12 Hour 6 Miler The event is capped at 100 runners. Registration closes on Octobe..

Enjoy vibrant New Hampshire foliage at the Fall Foliage Foot Races in Waterville Valley on Oct 12, 2025. Choose a flat 5K, a scenic 10 mile trail with a climb and downhill finish, or a 1 mile kids run. Limited spots remain for the 10 mile.

The North Face Race to the Summit is a mountain-top running event held at Stratton Mountain in Stratton, Vermont. The course covers about 2.18 miles with a 2,003-foot vertical climb, delivering a steep uphill challenge amid alpine terrain...

Run scenic mountain trails at Trapp Family Lodge in Stowe on October 18, 2025, with full and half marathon options that climb to Round Top for views of Mount Mansfield. Expect rugged single track, big climbs, friendly post race food and awa..

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 ston..

Event overview The Mansfield Uphill run is hosted by the Mansfield Nordic Pro Team at Stowe Mountain Resort on October 19, 2025. Proceeds will go directly to supporting the Pro Team athletes and program. The team is fundraising to help offs..

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 fest..

Join The Hamsterwheel in New Boston NH for a friendly 4 mile loop ultrarun with 6, 12, 24 and 30 hour solo and relay options. Scenic rail trail, night running, team camaraderie and quirky buckles make it a fun intro or a bold challenge.

Event information The Moreau Half takes place on Saturday, November 1, 2025, at Moreau Lake State Park in Gansevoort, NY (605 Old Saratoga Road). Start and finish are at the park beach. There is no fee to enter the park and parking is avail..

Event RutFest is the fifth annual Richmond Ultra Trail Festival held November 1-2, 2025 at Catamount Outdoor Family Center in Williston, VT. The event is community-focused and not for competition. It is organized as a 36-hour event over a w..

CircumBurke on Nov 1 at Victory Hill is an 18 mile singletrack, road and cart trail loop with short steep rocky sections that reward mountain running skills. Proceeds fund trail maintenance and the day offers aid stations, tacos and a beer.

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 a..

Mount Ascutney Vertical Backyard : Nov 22, 2025, Brownsville, VT The event is a "Last Person Standing" format held at Mount Ascutney in Brownsville, VT (449 Ski Tow Rd). Participants complete repeated laps; each hour they must asc..

Event details The Jeff RUN sonville Turkey Trot is scheduled for Thursday, November 27, 2025, in Jeffersonville, VT 05464. The event is organized by the Jeff RUN sonville Run Club and is described as the inaugural running of this town turke..