Trail Running Calendar Connecticut 2024-2025

The Cheshire Community YMCA's inaugural 5K Harvest Trail Race at Ives Farm offers a scenic running experience through fields and woods in Cheshire, CT. This family-friendly event features three races: a 5K, a Y Cup Relay for teams of three, and a Toddler Trot for children aged 6 and under. Participa..

The Woodbridge Trail Run + Woodland Walk is an exciting outdoor event taking place in Woodbridge, Connecticut, featuring a 4-mile trail run and a 2-mile woodland walk. Set in Alice Newton Street Park, participants will navigate a variety of terrains, including gravel, wood chips, and rocky paths, wh..

"8 Hours at the Farm" is a timed running event hosted by Steep Endurance at Gurski Farm/Williams Park in Brookfield, CT. Participants can choose from an 8-hour, 4-hour, or a 4-mile race, all set on a scenic, approximately 4-mile loop featuring a mix of single track and rolling farm trails. The event..

The Goodwin Trail Challenge is a running and hiking event that takes place on a ~13.5 mile linear trail passing through preserved lands in East Lyme, East Haddam, and Lyme. Participants park at Darrow Pond Park and are shuttled to the trailhead to run or hike back to their cars. In 2024, hikers can ..

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 Storybook Half Marathon, set in the scenic Roosevelt Forest in Stratford, CT, is a unique running event that invites participants of all skill levels, including runners, joggers, hikers, and walkers. This final edition of the race features a trail course with a mix of single and double track pat..

The Hartford Track Club 8K Cross-Country Challenge is a competitive running event taking place at the MDC Reservoir Complex in West Hartford, CT. This USATF-sanctioned race features a diverse course comprising gravel, trails, fields, and minor asphalt, accurately measured to 8 kilometers. Participan..

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 Roxbury Thanksgiving Day Charity Race is a 5K running event held annually in Roxbury, Connecticut. Participants run a 3.1-mile course at the Everett B. Hurlburt Community Park, promoting community spirit and charitable giving during the Thanksgiving holiday.The event encourages runners of all ag..

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 year marks the final edition of the race, which features a limited capacity of 50 participants, including both general and invitation-only entries. Runners are encouraged to embrace the holiday spiri..

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 a challenging running event held in Hamden, Connecticut, featuring 50K and 25K courses that showcase the diverse terrain of Sleeping Giant State Park. With over 30 miles of trails, participants will encounter a mix of smooth carriage roads and technical, rocky single..

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 Jack Bristol Lake Waramaug Ultra Races, taking place on April 27, 2025, marks the 51st anniversary of this historic event, recognized as the oldest ultras in Connecticut and the first 100K in the United States. Participants can choose from three distances: 100K, 50 miles, and 50K, all set on a s..

The Forgotten Forest Ultra Run in Stratford, CT, is a unique 9-hour trail running event held in Roosevelt Forest. Participants can choose to run, jog, hike, or walk on a well-marked loop with an elevation gain of 131 feet per lap. This event is limited to 25 participants, ensuring a personal experie..

The Blue 2 Blue Challenge is a demanding 50K trail race in New Haven, CT, known for its challenging terrain and technical trails. This event features over 6,350 feet of climbing and is designed for experienced runners, requiring participants to have completed a trail 50K within the past year. The co..

The Ansonia Trails 5K is a 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 of approximately 1.55 miles each, making it a fun and engaging experience for runners. With a limit of 100 parti..

The Ansonia Six Hour Trail Run is an exciting endurance event taking place at the Ansonia Nature Center in Ansonia, Connecticut. Participants will tackle approximately 1.9-mile loops of moderately technical singletrack trails, featuring about 170 feet of elevation gain per loop. Scheduled for the se..

The Brooksvale 12-Hour is an exciting running event held in Hamden, CT, featuring a 4.25-mile loop with a total elevation gain of 500 feet. Participants can challenge themselves to run distances ranging from a marathon (six loops) to 50 miles (twelve loops), making it suitable for various skill leve..