Trail Running Calendar Connecticut 2025-2026

Stonington Vineyards hosts the Wine Run Turkey Trot 5k at Stonington Vineyards in Stonington, CT. This timed 5k offers a run or walk on a two-lap cross-country course that begins and ends at the winery, weaving through vineyard lanes with occasional uneven footing. The atmosphere blends fitness with..

The Centerville Bank Thompson Turkey Trot is an annual event held at the West Thompson Dam Overlook Shelter in Thompson, Connecticut. It features a 5K timed trail run, a 3K untimed walk called the "Wobble" where dogs on leashes are welcome, and a free kids' fun run for children 12 and under. The eve..

Set in Tarrywile Park, Danbury, Connecticut, the Tarrywile Half Marathon offers three distances—10K, Half Marathon, and Marathon—through rugged park trails. The course is renowned for substantial elevation and technical Northeast single-track sections, delivering views of Danbury and the park’s tran..

Fall Fling 400, the CT Trailmixers’ ninth annual trail race, takes place at YMCA Camp Sloper in Southington, CT. The event offers two options: Fall Fling 400, where runners complete as many roughly two-mile loops as possible within a 400-minute limit (roughly 28 miles minimum), and the Spring Fling..

The Roxbury Thanksgiving Day Charity Race is a 5K event held annually in Roxbury, Connecticut. Scheduled for Thanksgiving Day, November 27, 2025, the race takes place at the Everett B. Hurlburt Community Park located at 18 Apple Lane.Participants run a 3.1-mile course, offering a community-focused a..

Tower Tag Challenge is a trail-running event at Sleeping Giant State Park in Hamden, Connecticut. Runners tackle the Tower Trail, a mostly smooth crushed-gravel carriage road that climbs about 600+ feet in 1.5 miles to the park’s Observation Tower, offering views of the surrounding landscape and, on..

The Frosty Forest 5K is a trail running event held in Roosevelt Forest, Stratford, Connecticut. This 5-kilometer race offers participants a chance to escape the roads and enjoy a scenic course through nature. Runners, joggers, hikers, and walkers are all welcome, with a requirement of some trail exp..

Located in Union, Connecticut, the Northern Nipmuck Trail Race is a 16-mile ultramarathon staged just outside Bigelow Hollow State Park. The course runs south on the Nipmuck Trail through the Yale-Myers Forest, crosses Barlow Mill Rd at mile 4, then reaches a turnaround at Boston Hollow before retra..

Sleeping Giant Trail Runs, hosted by Steep Endurance at Sleeping Giant State Park in Hamden, CT, offers challenging 25K and 50K trail races through Connecticut’s iconic park. The 25K loop features more than 3,000 feet of vertical gain across rocky and rolling singletrack via Yellow, Chestnut, White,..

Run Across CT is a coast-to-coast ultramarathon across Connecticut, starting in East Thompson and finishing at the Wakeman Boys & Girls Club in Southport. The course covers 123 miles and is offered as Solo 100k or Solo/Relay 200k (3–6 person teams). Runners traverse 25 towns, with about 57 miles on..

Jack Bristol Lake Waramaug Ultra Races run around Lake Waramaug in Kent, Connecticut, offering 100K, 50M, and 50K. One of the oldest ultras in the United States, it marks its 52nd anniversary in 2026 as part of the Mount to Coast 100K Series. The rolling, mostly flat course uses paved roads around t..

The Nipmuck South Trail Race is a 15.7-mile out-and-back trail run held in Mansfield, Connecticut, starting at Mansfield Hollow State Park. The course follows the scenic Nipmuck Trail alongside the Fenton River, featuring varied terrain including small bridge crossings, a climb to a 50-foot cliff, f..