Trail Running calendar near Cheshire 2024-2025

We have found 54 Trailruns within 80 miles of Cheshire. See below where and when you can find the races.

The Gardiner Dump Run is an exciting running event scheduled for September 21, 2025, in Gardiner, NY. Participants can choose between a 5k trail run or a 10k option, which consists of two laps of the 5k course. The race takes place on scenic single-track trails through wooded hillsides near the Wall..

October 2025

The IronHike Endurance Series, taking place at Mohawk Mountain in Cornwall, CT, is a unique multi-day event designed for hiking and trail running enthusiasts. Scheduled for October 2-5, 2025, participants can choose from various challenges, including individual and team formats, with distances rangi..

The Run for the Pumpkins Trail Run, organized by the Westerly Track & Athletic Club, is part of the WTAC Fall Race Series and will take place at Bradford Preserve in Westerly, Rhode Island. This event features a 10K, a 5K, and a children's 1K run for participants aged 10 and under. The courses showc..

The Nipmuck Trail Marathon, taking place in Ashford, CT, is a challenging 26.4-mile race that showcases the rugged beauty of the Nipmuck Trail. Participants can choose between the full marathon or a relay option, where two runners split the course. The race features a mix of terrain, including rocks..

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 Tesla Hertz Run is an exciting running event taking place in Rocky Point, NY, featuring various race distances including a 150 Miler, 100 Miler, 100K, 50 Miler, 50K, and 10 Miler. Set in a picturesque area of Long Island, the course consists of a 10.48-mile loop that offers a serene trail experi..

The Forbidden Forest 30 Hour Ultra Run is an exciting endurance event set in Stratford, CT, where participants can run, power-hike, or walk for up to 30 hours. This ultra run offers various distance options, including 26.2 miles, 50K, 50 miles, 100K, and 100 miles, allowing athletes to challenge the..

The Paine to Pain Trail Half Marathon is a unique running event set in the scenic woods and trails of five parks in Westchester County, New York. This race features a single-loop course that allows participants to experience diverse terrain, primarily consisting of dirt paths, while enjoying the nat..

The Mt. Tom Trail Race, organized by Beast Coast Trail Running, offers participants a chance to explore the scenic beauty of Mt. Tom during peak foliage.The event features challenging courses, including a solo 25k, a 2-person relay, and a solo 10k, all set within the rugged terrain of Mt. Tom State ..

Big Bear Squatchtoberfest is a trail running event hosted by Sassquad Trail Running in collaboration with the New York-New Jersey Trail Conference. Set in Harriman State Park, Tuxedo, NY, this event features a challenging half marathon and a 10K race, showcasing the park's rugged terrain and stunnin..

The Grills Trail Run, organized by the Westerly Track & Athletic Club, is part of the Fall Race Series and features both 10-mile and 10K races. Set in the scenic Grills Preserve in Westerly, Rhode Island, the event showcases beautiful trails, bridges, and riverfront areas, with a course comprising a..

November 2025

The Pocantico Hills Marathon, taking place in Rockefeller State Park, offers both a marathon and a half marathon. Participants will enjoy scenic, rolling courses with views of the Hudson River, featuring fields, stone walls, lakes, and forests. This event supports local organizations, including the ..

Rob's Trail Run Edition is a running event taking place at Stillwell Woods Preserve in Woodbury, NY. Scheduled for November 30, 2025, the event features two main races: a 5K Adult Trail Run for participants aged 19 and older, and a 5K High School or Youth Trail Run for those aged 18 and under. This ..

December 2025

The Tower Tag Challenge is a trail running event held at Sleeping Giant State Park in Connecticut, featuring a scenic course that ascends over 600 feet to the Observation Tower. Participants can choose between 4-hour and 8-hour options, completing loops on the Tower Trail, which includes a mix of cr..