Trail Running calendar near Chesterfield 2024-2025

The Fall Fling 400 is an annual trail running event organized by the CT Trailmixers, taking place at YMCA Camp Sloper in Southington, Connecticut. Participants can choose between two race options: a 400-minute race, where runners complete as many loops of a two-mile course as possible, and a 4-mile ..

The Brooksvale Trails Turkey Trot, taking place on November 24, 2024, in Hamden, CT, features both a 10K and a 5K trail race. This event serves as a food drive for the Hamden Food Bank, encouraging participants to bring non-perishable food items. The race offers a unique trail running experience, wi..

The Toonerville Trail Turkey Trot 5K is a festive running event taking place in Springfield, VT, on November 28, 2024. The course is a mostly flat out-and-back route along the scenic Black River, starting and finishing at the Toonerville Trail trailhead. Proceeds from the event will support local fo..

The Roxbury Thanksgiving Day Charity Race is a 5K running event held annually in Roxbury, Connecticut, aimed at promoting community spirit and supporting local charities. Participants run a 3.1-mile course at the Everett B. Hurlburt Community Park.The event encourages runners of all ages and abiliti..

Gorge après Gorge is an annual 5k trail run and free family fun walk held in the Hilltowns, featuring a scenic course along the Wild and Scenic Westfield River. Participants receive cookie medals, and unique knitted hats are awarded to top finishers. The event includes a community potluck with baked..

The Tower Tag Challenge is an exciting running event taking place at Sleeping Giant State Park in Hamden, CT. Participants can choose between 8-hour and 4-hour options, racing up and down the scenic Tower Trail, which leads to an Observation Tower. Each loop covers approximately 3.4 miles, allowing ..

Seth's Fat Ass 50K is an exciting running event taking place in Springfield, MA, at Forest Park. Participants can choose to complete one, two, or all ten loops of the 50K course, with a total time limit of seven hours to finish. The event promises to provide custom schwag for all participants, inclu..

The West Rock Winter Fat Ass Extravaganza is an exciting running event held in Hamden, CT, featuring 1.6-mile loops around Lake Wintergreen for a duration of eight hours. Participants can enjoy an aid station with various refreshments, including pizza, soup, and snacks. The event encourages self-sup..

The Frigus Snowshoe Festival, hosted at Moreau Lake State Park in Gansevoort, NY, offers a variety of snowshoe races including a 60K ultramarathon, 30K, 15K, 4.7-mile, and a kids' 1-miler. The 2025 event features new courses that explore the park's perimeter and scenic overlooks. Participants can ex..

The Northern Nipmuck Trail Race is a 16-mile trail running event held at Bigelow Hollow State Park in Union, CT. Revived in 2022 after being discontinued in 2012, the race maintains a low-key atmosphere and a friendly community spirit. The course follows the Nipmuck Trail, featuring technical terrai..

Spring on the Trails Endurance Runs is an exciting annual event held in Lagrangeville, NY, featuring timed races of 3 hours, 6 hours, 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 chos..

The Sleeping Giant Trail Runs is an exciting and challenging trail running event held in Hamden, Connecticut, featuring 50K and 25K race options. Set in the iconic Sleeping Giant Park, the course offers a mix of smooth carriage roads and technical, rocky singletrack trails, with over 3,000 feet of e..

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

The TARC Spring Classic, organized by the Trail Animals Running Club, takes place at the Jericho Town Forest in Weston, Massachusetts. This event offers multiple distance options, including 10K, Half Marathon, Marathon, and 50K, catering to runners of all levels. The course features a relatively fla..

The Jack Bristol Lake Waramaug Ultra Races, celebrating its 51st anniversary on April 27, 2025, is a prestigious ultra-running event held in Kent, Connecticut. It features three distances: 100K, 50 miles, and 50K, making it the oldest 100K race in the United States. The course consists of scenic, pr..

The Dandelion Dash and Mushroom Mile is a community running event taking place in Hadley, MA, featuring a 5K trail run/walk and a 1-mile fun run. Scheduled for May 4, 2025, the event aims to engage participants of all ages, promoting outdoor activity and family involvement. Proceeds from the event s..

The Blue 2 Blue Challenge is a demanding 50K trail race held in New Haven, Connecticut, known for its challenging terrain and technical trails. Participants will navigate some of the toughest trails in the state, including the Regicides and Quinnipiac Trails, with a total elevation gain of approxima..

The Ansonia Trails 5K is a vibrant running event taking place in Ansonia, CT, designed for participants of the 169 Society. This second annual race features a unique course consisting of two laps around a 1.55-mile loop, making it a fun challenge for runners. Limited to 50 participants, the event pr..

The TARC Wapack and Back is a challenging trail running event organized by the Trail Animals Running Club, taking place along the scenic Wapack Trail in Ashburnham, Massachusetts. Participants can choose from three distances: 21.5 miles, 43 miles, and 50 miles, with the course featuring rocky ledges..

The Sunapee Scramble is an exciting mountain racing event taking place on June 1, 2025, in Sunapee, NH. Participants will tackle a challenging course that begins at the base of Mount Sunapee, ascending via a service road to the summit, followed by a rapid two-mile descent back to the Base Lodge. The..