Trail Running calendar near Winchendon 2025-2026

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..

Mt. A Trail Challenge is an annual event held at Mount Agamenticus in York, Maine. Runners and walkers choose between a 5K or a 1-mile course.The race is timed in a traditional way by the York High School Cross Country Team, creating a friendly, community atmosphere. The 5K course climbs around the..

Codfish Bowl is the 57th annual cross-country meet held at Franklin Park, Boston, MA, and is part of the USATF New England XC Grand Prix. The event features a women's 5K and a men's 8K on modified courses (3 laps for the 5K, 4 laps for the 8K) because traditional courses are unavailable due to stadi..

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..

Winding Trails TRAIL RUNNING Series #5 is a Tuesday night event at Winding Trails in Farmington, Connecticut. The 2025 edition runs five races from August 26 through September 23, with a choice of 5K or 10K on an approximately 3-mile loop. Check-in and rolling start occur in the early evening at 50..

The Tunxis Trail Ultramarathon, held in Burlington, Connecticut, features challenging and technical trail races on the Tunxis Trail system, part of the Blue Blazed hiking trails. The event offers shorter distances this year, including an 8K (5 miles) and a 5K (3.1 miles), with staggered start times...

The Survival of the F.I.T.test - 30+ Hour Trail Ultra is a challenging endurance event held in Cumberland, Rhode Island. Participants can choose between two course options: a flat, fast 2.1-mile loop or a more rugged 4.2-mile trail loop used in previous years. The event offers multiple race formats..

Homecoming Chargers 5k Run/Walk is a community event in Blackstone, Massachusetts, scheduled for Saturday, September 27, 2025, at 175 Lincoln Street. The 5k Run/Walk uses Blackstone-Millville Regional's home cross-country course, offering a mix of grass and pavement with a finish on the track. The e..

Ocean State XC Invitational features the Ocean State 5K Trail Run, held at Goddard Park in Warwick, Rhode Island (1095 Ives Road). The 5K course winds through bay-side trails and grasslands, described as a fast, flat off-road route with the start and finish near the clubhouse for the public golf cou..

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 Moosup Valley 5K and 10K All Trail Race takes place in Moosup, Connecticut, on the newly restored Moosup Valley State Park Trail. This event features a 5K, a 10K, and a Kids Fun Run, all held on a 100% trail course that crosses only one dead-end road. The race starts and finishes at the Griswold..

Run for Nature in Lowell, Massachusetts returns to Shedd Park at 453 Rogers Street as a fundraiser hosted by the Lowell Parks and Conservation Trust. The event offers a 5K Run/Walk, a 10K Trail Run (no walk option), and a Kids 1-Mile Fun Run/Walk, a course through park trails and riverfront scenery...

Race for the Refuge takes place at Assabet River National Wildlife Refuge in Sudbury, starting at the Visitor Center. The event includes a 1-mile Walk, a 10K (one loop), a 30K (three loops), plus 3- and 6-hour timed races. The course uses double-track trails with ~2.5 miles of pavement per loop and..

CT Donut Run is a 31.5-mile charity group run in Connecticut, presented as a long, donut-filled endurance experience rather than a traditional race. The route centers in West Hartford and visits several donut stops, including locations in Newington, Berlin, Wallingford, and North Haven, finishing in..

The Houghton's Pond Trail Races take place in the scenic DCR Blue Hills Reservation in Milton, Massachusetts, just south of Boston. This event offers two trail race distances: 7 miles and 3.7 miles, both starting and finishing near the Houghton's Pond Visitor Center. The courses feature rolling terr..

NipMuck Trail Marathon, in Ashford, CT, features two options: the original NipMuck Trail Marathon (26.4 miles) and a two-person NipMuck Relay. The race uses a 13-mile middle segment of the Nipmuck Trail, running south to Route 44, back to the start, then north to Boston Hollow before finishing at Pe..

Groton Town Forest Trail Races, held at 163 West Main Street, Groton, MA, offer two trail distances: 9.5 miles and 3.4 miles. The courses are well-marked and feature a scenic loop through Groton Town Forest with no road crossings, combining narrow dirt roads and single-track trails over roots, rocks..