Trail Running calendar near Simsbury 2026-2027

A backyard ultra at Kenty's Farm on a 4.1666 mile loop where runners repeat hourly laps until one remains. Timed options of 6, 12 and 24 hours and single-lap entries are also available.

A trail 10k at Ward Pound Ridge Reservation plus a November virtual 100k challenge, with race results, photos, and a custom finisher woodallion for 100k finishers.

Trail race at Tarrywile Park in Danbury, CT, offering Marathon, Half Marathon and 10K on technical, hilly single-track trails with finisher medals, podium awards and a $600 half-marathon time bonus.

A trail race at Burlingame State Park in Charlestown on November 15, 2026, offering 4-mile and 8-mile courses around Watchaug Pond. It is the first race in the WTAC fall trail series with multi-race registration discounts.

A trail half marathon in Roosevelt Forest using eight 1.64 mile loops to total 13.1 miles. The event includes pavilion aid each loop, a book drive with Books4Everyone, costume prizes, podium awards, and participant swag.

Trail races at YMCA Camp Sloper in Southington CT feature a timed 400 minute loop event and a 4 mile two lap race on a roughly two mile wooded course. The event includes an aid station, chip timing, and finisher medals.

A Thanksgiving morning trail run supporting endometriosis research. Choose a run or walk on the 3.5-mile Mill Pond Trail, followed by complimentary yoga. All participants get a finisher medal and swag bag.

An annual Roxbury Road Runners charity race held on Thanksgiving Day, with proceeds supporting the Roxbury Scholarship Foundation and the Roxbury Ambulance Association. Results for the race are published as part of the club series.

Experience a 5K trail race through the scenic Stillwell Woods Preserve in Woodbury. This event honors the memory of Rob Lauterborn and supports the Center for Developmental Disabilities.

A trail running event at Sleeping Giant State Park on December 5, 2026, using the park's varied trails and scenic viewpoints. Organized by Steep Endurance with entry fees listed between 50 and 80 USD.

A 5K trail event through Roosevelt Forest in Stratford, CT on Dec 19, 2026, open to runners, joggers and walkers. Holiday costumes are allowed, awards recognize the fastest three men and women, and proceeds benefit local organizations.

Trail races at Sleeping Giant Park in Hamden, CT offering a 25K loop with 3K+ vertical and a 50K two loop option. The course features technical singletrack, steep rock scrambles, aid stations, and finisher medals.