Trail Running Calendar Connecticut 2025-2026

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)..

Run 30 haunting hours beneath a canopy of autumn leaves in Stratford CT on a rugged 2.23 mile loop with roots, rocks and one memorable climb. Limited to 50 runners, chase miles and earn a stunning 100 mile buckle.

Mohawk Mountain Race : Cornwall, CT The Mohawk Mountain Race takes place at Mohawk Mountain Ski Area in Cornwall, CT (46 Great Hollow Road). The event offers four distance options: Marathon Half Marathon 10K 5K Registration closes on Octo..

Goodwin Trail Challenge (October 12, 2025) The Goodwin Trail Challenge is a registered mountain bike event held on October 12, 2025. Registration is required through BikeReg and includes a donation to East Haddam Land Trust that provides a..

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 ben..

Take on the rugged Bimblers Bluff 50K in Guilford Connecticut on October 19, 2025. Enjoy a challenging off road course through scenic woodlands and rocky single track while supporting local land conservation.

Cheshire Community YMCA 5K Harvest Trail Run in Cheshire, CT, is a race around Ives Farm. The all-ages event winds through fields and trails on the farm, starting and finishing at the remodeled barn. Proceeds support the YMCA’s Cheshire com..

Run through the vines at Stonington Vineyards in this chip timed 5k that finishes with a wine pour, unique finisher medal, and a shatterproof wine glass. Two laps through scenic vineyard trails make it perfect for runners and walkers.

Overview 8 Hours at the Farm is a timed trail running event presented by Steep Endurance on November 2 in Brookfield, Connecticut. The event is held at Gurski Farm / Williams Park with race headquarters and the start/finish located in the b..

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,..

Event details The Tarrywile Half Marathon is a trail running event held on November 16 at Tarrywile Park, 70 Southern Blvd., Danbury, Connecticut. The event offers three distances: Marathon Half Marathon 10K Registration tiers vary by dat..

Event details Fall Fling 400 is organized by the CT Trailmixers at YMCA Camp Sloper in Southington, Connecticut on November 22, 2025. The event offers two main entry options: 400-minute run on a roughly two-mile loop 4 Mile (two laps of th..

Brooksvale Trails Turkey Trot : November 23, 2025 The Brooksvale Trails Turkey Trot takes place in Hamden, CT, at Brooksvale Park (524 Brooksvale Avenue). The event is organized by Live Loud Running and the Town of Hamden and is the third a..

Join the Roxbury Thanksgiving Day Charity Race for a festive 5K through Everett B. Hurlburt Community Park. Support local causes and burn off holiday calories with friends and neighbors this Thanksgiving morning.

Test your endurance at the Tower Tag Challenge in Sleeping Giant State Park with 4 hour and 8 hour timed options on repeated 3.3 mile loops to the Observation Tower. Bring your own cup, enjoy finisher swag, and support the park.

Event overview The Frosty Forest 5K takes place in Roosevelt Forest in the Town of Stratford, Connecticut on Saturday, December 13, 2025. The event is a trail run over a 5K distance. Participants may wear holiday costumes during the event...

Event overview The West Rock Winter Fat Ass Extravaganza is scheduled for December 28, 2025 in Hamden, CT near Lake Wintergreen. The event is an eight-hour looped run using a 1.6-mile loop around Lake Wintergreen with about 65 feet of eleva..

Event overview The Enchanted Forest Ultra Run is a trail ultramarathon held at Roosevelt Forest, 700 Peters Lane, Stratford, CT. The event is offered as a 6-hour format and as a 50K distance. Field size is limited to 50 participants. Regist..

Run 16 miles of rugged single track through Bigelow Hollow and Yale Myers Forest to Boston Hollow in this intimate, capped trail race near Union, CT. Limited to 100 runners, the event supports local trail organizations.