Trail Running calendar near Winchendon 2025-2026

Winding Trails TRAIL RUNNING Series #2 takes place in Farmington, Connecticut, at Winding Trails. The five-evening series runs Tuesdays from August 26 through September 23, 2025. Runners can choose either a 5K or 10K distance, each built on a 3-mile loop through the trail system.Check-in and the rol..

The Springfield Dam Run, held in Springfield, Vermont, offers a family-friendly running event featuring three races: a Kids 1/2 Mile Fun Run for children 12 and under, a new Maniac Mile one-mile sprint for ages 10 and up, and the traditional 3.1-mile Springfield Dam Run. The main race takes place on..

The Cross-Connecticut Run for Mental Health Awareness is a unique 56-mile group running event held annually in Connecticut, following the scenic and flat Farmington Canal Heritage Trail from West Suffield to New Haven. This non-competitive challenge supports Mental Health Connecticut through fundrai..

Set in the Great Brook Farm State Park in Carlisle, Massachusetts, with start/finish at Hart Barn Ski Center, the TARC Fall Classic offers distances of 50 miles, 50K, 20 miles, half marathon, 10K, plus a free youth fun run and the Yeti Mischief Mile. The looped course weaves through woods and fields..

Granite Gorge Yo-Yo Run is a mountain race held in Keene, New Hampshire. The course is run mostly on ski trails with some single-track, totaling about 4.9 miles with roughly 1,650 feet of ascent and descent. The race earns its name from the steep up-and-down sections that feel like a Yo-Yo as you cl..

The Wicked Mudder will take place in Southwick on Sunday 7 September 2025. You can run between 5 and 5 kilometers.

Run to Fall 5K is a community cross-country event held at Coe-Brown Northwood Academy on the 1st New Hampshire Turnpike in Northwood, New Hampshire. The program features a 5k cross-country race on the CBNA course, a 2.5-mile trail walk, and youth races on the NH Youth State Meet Course, plus a kids’..

Winding Trails TRAIL RUNNING Series #3 is a Tuesday-night trail race series held at Winding Trails in Farmington, Connecticut. The 2025 edition runs five races from late August through late September, with participants choosing either a 5K or a 10K distance. Runners cover a roughly 3-mile loop on tr..

The Mountain Goat Cabin Trail Run takes place at the Merck Forest and Farmland Center in Rupert, Vermont. The main event features a challenging 7-mile loop with approximately 1,500 feet of elevation gain, winding through scenic trails and forest roads. Runners experience two historic cabins, Ned's P..

The Lucy Mac 5K9 is a trail running event held at Ascutney Outdoors in Brownsville, Vermont. Scheduled for September 13, 2025, it features a timed 5K race and a 1-mile race option, welcoming runners, walkers, and dogs. The course offers a scenic Vermont adventure with handcrafted trails at the weste..

PCS Harvest Hustle 5K & Kids Run is a fundraising event at Pomfret Rec Park in Pomfret Center, CT, benefiting the Pomfret Community School PTO. It offers a Kids Fun Run and a trail 5K. The 5K winds through the Pomfret Forest on a technical, single-track wooded trail—rocky with roots and ups and down..

The Veterans Count Nashua 5k Fun Run & Walk will take place in Nashua on Sunday 14 September 2025. You can run between 5 and 5 kilometers.

The Pisgah Mountain Trail Races, held in Pisgah State Park, Chesterfield, New Hampshire, feature two challenging trail distances: a 50K and a 23K. Organized by the Red Clover Rovers, this event serves as a fundraiser for the New Hampshire Special Olympics, with all profits supporting their mission...

The Gunstock 5K and Canicross 5K take place at Gunstock Mountain Resort in Gilford, NH, as part of the annual Food Truck Festival. The event features a 5K trail run and a Canicross 5K where participants run with their dogs, followed by a 100m fun run for children under five. The course is a loop aro..

Winding Trails TRAIL RUNNING Series #4 is a five-race Tuesday-night trail series in Farmington, CT. Race #4 runs from Aug 26 to Sep 23, 2025, offering 5K or 10K options on a roughly 3-mile loop. Check-in and a rolling start take place at Winding Trails, 50 Winding Trails Drive.Registration is availa..

The Hooksett Kiwanis 5K Trail Race, held in Hooksett, New Hampshire, is a scenic trail run starting at Heads Pond trail and finishing at the Hooksett Public Library. The course features a hard-packed stone dust surface and wooded conservation trails, offering a natural and enjoyable running experien..

All of the Above Trail Fest is held at Northfield Mountain Recreation Area in Northfield, Massachusetts. A collaboration between Beast Coast Trail Running and The Venture Out Project, the festival centers on inclusivity for queer and transgender runners and their allies, celebrating people over boxe..

Bear Brook Trail Races take place at Bear Brook State Park in Allenstown, New Hampshire. The event offers three trail races: Marathon, Half Marathon, and 10K (the 10K follows Mindy’s Loop). The Marathon doubles the Half Marathon route.Runners encounter diverse terrain—from beautiful single-track thr..

The Mt. A Trail Challenge is an annual running event held at the summit of Mount Agamenticus in York, Maine. The 9th edition features two courses: a 5K and a 1 Mile trail run, hike, or stroll.The race is uniquely timed with stopwatches by the local York High School Cross Country Team, emphasizing a..

The BLS Wolfpack 5K Cross Country Run or Walk is a 5K event in Boston’s Franklin Park, using the historic Franklin Park cross-country course. It brings together the Boston Latin School community—students, staff, families and alumni—for a morning of running or walking, with the pep band adding energy..