Trail Running calendar near Rupert 2025-2026

The TAM Trek is a trail race and fun run that raises funds for the Trail Around Middlebury (TAM). The 2025 edition is the 22nd annual event and takes place on September 21, 2025, in Middlebury, Vermont. All distances start and finish at Wright Park. The Trail Around Middlebury was begun in 1989 and..

The Vermont 50 Ultra Run is part of the Vermont 50 endurance weekend held at Ascutney Outdoors in West Windsor, Vermont. It includes a 50‑mile Ultra Run and a 50K Run, plus related relay options and other activities that showcase a challenging yet scenic Vermont landscape. Runners traverse the hills..

The Flutters and Foliage Endurance Run, held in Cohoes, NY, is a unique ultra running event supporting Flutters of Hope, a nonprofit aiding individuals and families affected by eating disorders. Now in its third year, the race features multiple endurance challenges including 1-hour, 3-hour, and 6-ho..

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 forests, ponds and marshes with about 700 feet of elevation ga..

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 primarily flat with a few gentle rollers, and has no road crossings...

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..

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 more challenging rolling singletrack and elevation. Runners..

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 trail and a 1 Mile Fun Run. The course showcases rugged terrain..

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 Midstate Massive Ultra Trail is a multi-distance, point-to-point trail race organized by New England Race Events in New Ipswich, New Hampshire, with routes extending into nearby Massachusetts and Rhode Island. It offers 100-mile, 50-mile, and 50-kilometer options, tracing the historic Midstate T..

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. The race is timed with live results and leaderboards, with o..

The Mt. Tom Trail Race takes place on October 18, 2025, with the start/finish and parking at Bray Lake in Mt. Tom State Park. The event is a nonprofit fundraiser that supports the Kestrel Land Trust. Registration fees are non-refundable and non-transferable. Check-in is held one hour before each ra..

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 Veeder Tree Farm 5K is a running event held in Earlton, New York, at 1235 High Hill Rd. Scheduled for October 19, 2025, the race offers multiple categories including a 5K, 5K Trail Run, and combinations thereof, with options for students as well. The course features a mix of trail and traditiona..

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..

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..

Race for DFL is a last-runner-standing backyard ultra held at Kenty’s Farm in Winchendon, Massachusetts. The event uses a single lap of about 4.17 miles, with a course mixture of grassy field, forest trail, crushed gravel bike path, and a dirt road, totaling around 150 feet of elevation gain per lap..

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..