Trail Running calendar near Chester 2025-2026

The Spring on the Trails Endurance Runs is an exciting annual event held in Lagrangeville, NY, featuring timed races of 3, 6, and 12 hours on a scenic 5k trail loop with approximately 250 feet of elevation gain per lap. Participants aim to complete as many loops as possible within their chosen time..

The Enchanted Forest Ultra Run is a captivating 6-hour ultra event taking place in Roosevelt Forest, Stratford, CT. Participants can run or hike a 2.3-mile loop trail, aiming for as many miles as possible within the time limit or striving for the 50K milestone. This event is suitable for both novice..

The Northern Nipmuck Trail Race is a 16-mile trail running event held in Union, Connecticut, organized by the Shenipsit Striders. Revived in 2022 after a hiatus, the race maintains a friendly, low-key atmosphere, attracting runners of all levels. The course traverses the Nipmuck Trail, featuring tec..

The Sleeping Giant Trail Runs, set in the iconic Sleeping Giant State Park in Hamden, CT, promises to be one of the toughest trail races in the Northeast. Participants can choose between a challenging 25K or a grueling 50K course, featuring over 30 miles of diverse terrain, including smooth carriage..

The Mt. Toby Ultra is a trail running event offering three distance options: 13k, 24k, and 50k, each showcasing the scenic beauty of Mt. Toby.The race serves as a fundraiser for Girls on the Run of Western Massachusetts, promoting joy, health, and confidence among girls through running. Participants..

The Run for the Rescue 5K Trail Run/Walk is scheduled for April 5, 2025, at Blydenburgh County Park in Hauppauge, NY. This dog-friendly event encourages participants to bring their leashed pets along for the run. The course features a mix of trails suitable for all experience levels. Registration op..

The Farm & Forest All-Terrain 5K & Kid Fun Run is an exciting outdoor running event scheduled for April 6, 2025, in Stamford, Connecticut. Participants will enjoy a scenic 5K course that begins at the Fedele Family Plaza and winds through Heckscher Farm, featuring various animals and beautiful lands..

The John Jay Community Trail Race is a competitive running event taking place in Cross River, NY, featuring a 5k race, a 4k Jay Walk, and a Kids Jay Dash. The 5k race is set on the newly developed John Jay Community Cross Country Trail, which includes challenging wooded terrain. The 4k Jay Walk offe..

The "4 in the Forest" event is a trail running race taking place in Irvington, NY, featuring a challenging 4-mile course through the scenic Irvington Woods. Participants can look forward to a memorable experience, complete with a custom-designed race patch and medal. The event encourages community i..

The 10th Annual F.O.R 5k Trail Race will take place at the McDonald Nature Preserve in Wilbraham, MA. This family-friendly event encourages participants of all ages to enjoy the outdoors while supporting the Recreation Maintenance Fund for local parks. The race features a scenic course rated easy to..

The Bunny Trail 5K, organized by the Never Stop Running Foundation, is set to take place at Bethpage State Park on April 13, 2025. This annual event invites participants to enjoy a scenic run or walk along beautiful trails, with a free kiddie run also available. The course features mostly flat terra..

The Brookhaven Trail 15K and 4 Mile Trail Run is set to take place at Brookhaven State Park in Wading River, NY. This popular event features a challenging course that includes various trail conditions, from single-track paths to sandy sections, all within the scenic woodlands of Suffolk County. Part..

The Traprock 50 is a challenging trail running event held at Penwood State Park in Bloomfield, CT, featuring two race distances: a 50K and a 17K. The course consists of approximately 10.5-11 miles per loop, with the 50K requiring three loops and the 17K one loop. Runners will navigate a mix of techn..

Shore2Shore is a scenic running event taking place in East Islip, NY, featuring a 50K and a 25K race along the beautiful Suffolk County Long Island Greenbelt Trail. The race starts at Sunken Meadow and concludes at Heckscher State Park, offering participants a picturesque route through towns and tra..

The Lake Mohegan Trail Race is a women's only trail running event held in Fairfield, CT, organized by Steep Endurance. Aimed at promoting trail running among women, the event typically sees 30-40% female participation, with over 125 runners in 2024. The race features three distances: a 5K, a 10K, an..

The Radish Rambler 5k at White Barn Farm is a fun and engaging trail run/walk/hike set in the scenic conservation land of Wrentham, Massachusetts. Scheduled for April 26, 2025, this event welcomes participants of all ages and skill levels, marking the opening day of the farm and an Earth Day celebra..

The Jack Bristol Lake Waramaug Ultra Races, taking place on April 27, 2025, is a celebrated ultra-running event in Connecticut, marking its 51st anniversary. This historic race features three distances: 100K, 50 miles, and 50K, all set around the scenic Lake Waramaug. Participants can expect well-st..

Leatherman's Loop is a popular 10k trail race held annually in Cross River, NY, attracting participants of all ages from 7 to 107. The event is known for its scenic course and community spirit, and entry is determined through a lottery system due to high demand. The registration fee includes the par..

The Conquer The Trail 5k is an annual running event celebrating its 10th year, taking place at Mercy University in Dobbs Ferry, NY. This year, the race will feature a flat and fast out-and-back course along the Old Croton Aqueduct Trail, with a single hill before the finish. Proceeds from the event..

The Forgotten Forest Ultra Run is a unique trail running event held in Roosevelt Forest, Stratford, CT. Scheduled for May 3, 2025, this 9-hour ultra trail race invites participants of all levels, including runners, joggers, hikers, and walkers, to complete as many miles as they can on a well-marked..