Trail Running calendar near Chester 2025-2026

The Cross-Connecticut Run for Mental Health Awareness is a unique 56-mile group running event held annually in Connecticut, traversing the state north to south along the scenic and flat Farmington Canal Heritage Trail. Starting in West Suffield and ending at New Haven Harbor, the course passes throu..

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

The Macedonia Trail Race, held in Macedonia Brook State Park in Kent, Connecticut, offers trail runners a unique experience with its lush forest trails, challenging climbs and descents, and stunning viewpoints including Cobble Mountain, where runners can see the Catskill Mountains on clear days. Now..

The Wahaneeta Trail Run is a 5K trail race taking place in Westerly, Rhode Island, as part of the WTAC Fall Race Series. This event emphasizes a "no frills" approach, foregoing modern amenities like t-shirts and extensive awards to keep costs low and logistics simple. Participants can enjoy a classi..

The Pawling 24 Hour Trail Running Festival, held in Pawling, NY at Lakeside Park, offers runners a challenging and festive endurance experience. Participants can choose from 3, 6, 12 (including a night start), or 24-hour timed races on a 1.68-mile loop course featuring pavement, grass, and single-tr..

Run for the Hills is an annual 5K trail run and walk held at the Oswegatchie Hills Nature Preserve in Niantic, Connecticut. The event offers participants a scenic course around Clark Pond and along the preserve's perimeter, showcasing over 450 acres of coastal forest. Designed as a fundraiser, proce..

The Storybook Half Marathon is a friendly trail running event held in Roosevelt Forest, Stratford, Connecticut. The course consists of 1.64-mile loops repeated eight times, totaling the half marathon distance of 13.1 miles. Runners, joggers, hikers, and walkers are all welcome, with a four-hour time..

The Wine Run at Westport Rivers Vineyard & Winery is a scenic running event scheduled for September 14, 2025, in Westport, MA. Participants can enjoy a beautiful trail run through the vineyard, covering approximately 3 miles amidst picturesque farms and vines. After the race, attendees can indulge i..

The Charlie Stavros Memorial Beach Run is a free, end-of-summer 3-mile running event held at Westerly Town Beach, Rhode Island. Organized by the Westerly Track Club and the Stavros family, the race features a scenic route that includes a 1.5-mile out-and-back course along the beach at low tide. This..

The Cockaponsett Trails to a Cure is a running event taking place in Chester, Connecticut, featuring two trail races: a 4-mile and a 9-mile course through the scenic Cockaponsett State Forest. The course includes challenging terrain with roots, rocks, and hills, and is designed to accommodate runner..

The Angevine Farm Trail Festival, held annually in Warren, Connecticut, offers a scenic and challenging trail running experience in the Northwest corner of the state. The event features multiple distances including a half marathon, a new 8-hour race on a 1.25-mile farm loop, and 5K races including a..

The IronHike Endurance Series is a unique multi-day event taking place at Mohawk Mountain in Cornwall, CT, from October 2 to October 5, 2025. Participants can choose from various challenges, including individual and team formats, with distances ranging from 15 to over 152 miles, featuring significan..

The Run for the Pumpkins Trail Run is part of the WTAC Fall Race Series, taking place at Bradford Preserve in Westerly, Rhode Island. Scheduled for October 4, 2025, the event features a 10K, a 5K, and a children's 1K run for participants aged 10 and under. The courses showcase the natural beauty of..

The Run the Vineyards - Pindar Fall 8K is a scenic running event set in the picturesque Pindar Vineyards in Peconic, NY. Participants can choose between an 8K and a 5K race, both featuring flat courses primarily on hard-packed dirt trails and grass, making them walker-friendly. The event includes ch..

The NipMuck Trail Marathon, held in Ashford, Connecticut, is a challenging 26.4-mile trail race along the scenic Nipmuck Trail. The course features diverse terrain including rocks, roots, mud, and wood bridges, with a route that heads south 6.2 miles to Route 44 and back, then north 7 miles to Bosto..

The Tesla Hertz Run, held in Rocky Point, NY, is a multi-distance ultramarathon event featuring races from 10 miles up to 150 miles. The course is a scenic 10.48-mile loop through the pine barrens of Long Island, offering a remote trail experience with minimal outside interaction. Runners benefit fr..

The Forbidden Forest 30 Hour Ultra Run is an epic endurance event held in Stratford, Connecticut, offering runners up to 30 hours to complete distances ranging from a marathon (26.2 miles) to 100 miles or more. The course features a challenging 2.23-mile loop with roots, rocky terrain, and a notable..

The Mohawk Mountain Race, held at Mohawk Mountain Ski Area in Cornwall, Connecticut, offers a challenging trail running experience with 5K, 10K, Half Marathon, and Marathon distances. The course features steep ascents and descents on ski mountain trails, including the Wildwood, Timber, Pine, Laurel,..

The Paine to Pain Trail Half-Marathon is a distinctive trail race held in Westchester County, New York, starting at the historic Thomas Paine Cottage in New Rochelle and finishing at New Rochelle High School. This 13.1-mile single-loop course traverses the woods and trails of five different parks, o..

The 2025 Never Stop Running Foundation Great Pumpkin Dash Trail 5K is a scenic trail run/walk held at Blydenburgh County Park in Smithtown, NY. The course features shaded trails with a mix of dirt roads and hard-packed surfaces, suitable for first-time trail runners, though strollers and wagons are..