Trail Running calendar near Stonington 2026-2027

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.

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.

Experience a winter trail challenge at Hale Education featuring 15 mile and 30 hour options. Navigate three unique loops through the Massachusetts woods while testing your endurance and self reliance in cold weather conditions.

A 123 mile point to point ultramarathon across Connecticut featuring about 57 miles of trail, a 36 hour cutoff, solo and relay options, and belt buckles for 200K finishers.

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.