Trail Running calendar near Chesterfield 2024-2025

The Tarrywile Half Marathon, held in Danbury, CT, is known for its challenging trail course featuring significant elevation gains and technical terrain. Participants can choose from three distances: Half Marathon, Marathon, and 10K. The half marathon course includes rocky and hilly sections, with a ..

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 10K and 5K trail races. This event serves as a food drive for the Hamden Food Bank, encouraging participants to bring canned or boxed food items. The race offers a unique trail running experience, with..

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 benefit Meals on..

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..

The Dreadmill 48 Hour Endurance Challenge is a unique virtual running event where participants aim to complete 100 miles on a treadmill within a 48-hour timeframe. Taking place throughout December, runners can choose any two days to complete their distance, allowing for breaks and flexibility. Parti..

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 a variety of food options, including pizza, soup, grilled cheese, and snacks, with an aid station availabl..

The BURCS Treadmill Marathon & 50K is a unique virtual running event taking place from January 1 to January 31, 2025. Participants can choose to complete a marathon, a 50K, or both within a 24-hour period on a treadmill. The event encourages runners to log their distances while providing proof throu..

Satan's Sidewalk is a unique virtual running event designed to challenge participants during the cold winter months in New England. Runners can choose between a 66.6-hour treadmill odyssey or a fixed distance of 66.66K. The event encourages participants to log their miles while adhering to specific ..

The Ladybug 50k is a virtual running event held in March 2025, honoring the memory of Cathy Troisi, a dedicated runner and philanthropist. Participants can complete the 50 km distance at their convenience, whether on a treadmill, track, trail, or road, within a 24-hour period. Registration is open u..

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 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..

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 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..

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

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..