Trail Running Calendar Connecticut 2025-2026

Forbidden Forest 30 Hour Ultra Run takes place in Roosevelt Forest, Stratford, Connecticut, October 11-12, 2025. Runners choose a personal challenge on a 2.23-mile loop that weaves through roots, rocky terrain, and a standout hill dubbed "OMG." Competitors can tackle 26.2M, 50K, 50M, 100K, 100 Miles..

Gemstone Sparkle Sprint 5k is a community trail run in Wilton, Connecticut, on Gemstone Farm (144 Huckleberry Hill Rd). The second annual event offers a scenic 5k trail course suitable for all abilities (strollers not allowed on the course) with a festive sparkly theme inviting participants to dress..

Mohawk Mountain Race, held at Mohawk Mountain Ski Area in Cornwall, CT, is a Steep Endurance trail event offering 5K, 10K, Half Marathon, and Marathon distances. The course climbs the mountain on Wildwood and Timber Trails, then traverses Pine, Laurel and Deer Run Trails, before a summit return via..

The Tackle the Trail - Pomfret, CT will take place in Pomfret on Saturday 18 October 2025. You can run between 10 and 42 kilometers.

Tom Centinaro Memorial "Dam" Race is a 3.5-mile trail run/walk hosted by the Wolcott Lions Club in Wolcott, Connecticut. The race unfolds on the scenic, flat Mill Pond Trail at Woodtick Recreation, 201 Nichols Road. This community event benefits local charities and the Tom Centinaro Lions scholarshi..

Bimblers Bluff 50K is an off-road ultramarathon in southern Connecticut, starting at Guilford Lakes School in Guilford. The 50-kilometer course weaves through interconnected woodland preserves, using rolling forest roads and rocky single-track. The route is notable for not requiring repeated loops,..

8 Hours at the Farm, held in Brookfield, CT, is a Steep Endurance trail running event on a rolling country course at Gurski Farm/Williams Park. The race features an approximately 4-mile loop with single-track and farm trails, plus options for 8-hour, 4-hour, and 4-mile races. The event emphasizes a..

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 Marathon, Half Marathon, and 10K trail distances. The course is renowned for its toughness, with close to 3,000 feet of elevation and substantial Northeast single-track, featuring rocky, rooty, and hilly terrain. The rou..

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 held at Sleeping Giant State Park in Hamden, Connecticut. The course follows the Tower Trail, a crushed-gravel carriage road that climbs about 600 feet in 1.5 miles to the Observation Tower, offering sweeping park views and, on clear days, Long Island Sound. Each Tower Tag att..

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..