Trail Running calendar near Simsbury 2024-2025

The Storybook Half Marathon, taking place in Roosevelt Forest, Stratford, CT, is a friendly and inclusive running event that invites racers, joggers, hikers, and walkers to participate. This will be the final edition of the race, featuring a scenic trail course with a mix of single and double track ..

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 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..

Rob's Trail Run Edition is a running event taking place at Stillwell Woods Preserve in Woodbury, NY, on December 1, 2024. The event features two main races: a 5K Adult Trail Run and a 5K High School or Youth Trail Run, catering to participants of different age groups. This event aims to honor the me..

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 ..

The Frosty Forest 5K is a unique running event taking place in Roosevelt Forest, Stratford, CT. This will be the final edition of the race, inviting participants to enjoy a scenic trail run while embracing the holiday spirit. Runners can choose to run, jog, hike, or walk the 5K course, with the opti..

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 Dar Snowshoe Scramble is a fun and low-key running event that offers participants the option to snowshoe or trail run, depending on snow conditions. The course is approximately 3.8 miles, with potential variations between 5k and 10k. The event emphasizes enjoyment over competition, with no forma..

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..

Big Bear Squatch North is an exciting running event held in Bear Mountain, NY, featuring a half marathon and various distances ranging from 5K to 50K. The course has undergone multiple reroutes in recent years due to storm damage, particularly from July 2023, which has affected trail accessibility. ..

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 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..

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 scheduled for April 27, 2025, and features a lottery system for entry due to its high demand. The registration fee includes the park's entry fee, streamlin..

The Bear Mountain Trail Challenge is an exciting running event held at Bear Mountain State Park, located just an hour from New York City. Participants can choose from three race distances: a 50K, a half marathon (21K), and a 10K. The course features a diverse range of terrain, including short climbs..

The Forgotten Forest Ultra Run is a unique 9-hour trail running event held in Roosevelt Forest, Stratford, CT. Celebrating its 10th and final edition, participants can choose to run, jog, hike, or walk on a well-marked loop with an elevation gain of 131 feet per loop. The event is limited to 25 part..