Trail Running calendar near Cumberland 2025-2026

The Anchor Down Ultra will take place in Bristol on Friday 8 August 2025. You can run between 6 and 24 kilometers.

The Stonington Cross Country 5K is a free running event held at Stonington High School in Pawcatuck, Connecticut. The course begins with a loop on the school track, followed by a half-mile run on quiet, dead-end streets within the campus. Runners then transition to a mix of single- and double-track..

The Tarc Summer Classic is a trail running event held at Noon Hill Reservation in Medfield, Massachusetts, featuring multiple race distances including 10 miles, 50K, and 40 miles. The course is a scenic, mostly forested loop with undulating terrain, roots, rocks, and a notable viewpoint at Noon Hill..

The Shenipsit Striders 50th Fatass is a celebratory running event held at Crandall's Park Pavilion in Tolland, Connecticut. Marking the club's 50th anniversary, the event features an 8-hour window where participants run multiple 5K loops on a trail course starting and finishing at the pavilion. Runn..

The Midstate Massive Course Preview is a pre-race recon run held in Spencer, Massachusetts, offering runners a chance to explore a 13.1-mile section of the Midstate Trail used in both the 50-mile and 100-mile races. The run covers the trail segment between Aid Stations 6 and 8, providing participant..

The GTA Challenge is a 10K trail race held in Greenfield, New Hampshire, organized by the Greenfield Trail Association to support local trail maintenance. The course features a mix of class 6 roads, double track, and single track trails with natural obstacles like rocks and roots, offering a challen..

The Watermelon Wobbler 5k is a fun, off-road trail run held at White Barn Farm in Wrentham, Massachusetts. This 5K race takes participants through scenic conservation land and farm property, featuring dirt and gravel paths with natural obstacles like rocks, roots, and elevation changes. Open to all..

Greenbelt's Vineyard Hill Trail Run is an annual trail running event held in South Hamilton, Massachusetts, located on the scenic town line of Hamilton and Topsfield. The race offers 5K and 10K distances that traverse Vineyard Hill, sections of Bradley Palmer State Park, the Bay Circuit Trail, and G..

The Old Goat Track Club XC Classic is a 5K cross-country race held at Water's Farm in Sutton, Massachusetts. Scheduled for August 24, 2025, it features separate Women's and Men's Open 5K races. The event serves as the first race in the USATF New England XC Grand Prix series and is part of the USATF..

The Foot It for Felix 5K is a scenic running and walking event held at Felix Neck Wildlife Sanctuary in Edgartown, Massachusetts. Participants traverse beautiful nature trails featuring pine needle-covered paths, fields of goldenrod, and stunning views of Sengekontacket Pond and State Beach. The cou..

The TARC Fall Classic is a popular trail running event held at Great Brook Farm State Park in Carlisle, Massachusetts, offering a range of distances including 10K, half marathon, 20 mile, 50K, and 50 mile races, plus a Yeti Mischief Mile and a free youth fun run. The courses wind through scenic New..

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..

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

Run for the Hills is an annual 5K trail run and walk held at the Oswegatchie Hills Nature Preserve in Niantic, Connecticut. The event features a scenic course that runs by Clark Pond and around the perimeter of the preserve, offering participants beautiful coastal forest views across more than 450 a..

The Wahaneeta Trail Run is a 5K trail race held in Westerly, Rhode Island, located on Moorhouse Road. Scheduled for September 13, 2025, it is the first event in the WTAC Fall Trail Race Series, which includes four races with a discount for registering in multiple events. This race embraces an "old s..

The PCS Harvest Hustle 5K & Kids Run is a community-focused event held at Pomfret Rec Park in Pomfret Center, Connecticut. It features a 5K trail run and a kids' fun run of half a mile, supporting the Pomfret Community School Parent Teacher Organization. The PTO uses funds raised to enhance educatio..

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 The Wine Run at Westport Rivers Vineyard & Winery will take place in Westport on Sunday 14 September 2025. You can run 3 miles.

The Charlie Stavros Memorial Beach Run will take place in Misquamicut on Friday 19 September 2025. You can run 3 miles.

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..