Trail Running Calendar Connecticut 2026-2027

A classic 16-mile trail run on Connecticut's Nipmuck Trail, known for its technical terrain and old-school vibe. Organized by the Shenipsit Striders, the event supports local trail stewardship. Registration is capped and no race day signups..

Course and Distances The Sleeping Giant Trail Runs take place at Sleeping Giant State Park in Hamden, Connecticut. The event offers two distances: 25 km: A single loop with over 3,000 feet of vertical gain. 50 km: Two loops of the 25 km co..

Course and Distance The Run Across CT 123 is a point-to-point ultramarathon that travels coast-to-coast across Connecticut, covering approximately 123 miles (200K). The route passes through 25 towns, starting in East Thompson and finishing..

The Bimbler's Bash is a popular annual 10K trail run through the technical, rocky paths of Guilford's Westwoods. This entirely off-road event supports local land conservation and is known as a major single-distance race in Connecticut.

Run a unique quarter marathon distance on the paved trails of West Hartford Reservoir. This chip timed 6.55 mile race features a two loop course with post race treats and age group awards.

A 5K race winds through Heckscher Farm and forest trails at the Stamford Museum and Nature Center. Children can join a short fun run past friendly farm animals. The event offers a unique running experience surrounded by nature.

The Traprock 50 features a rugged 50K and a 17K trail race on the rocky, rolling loops of Penwood State Park. It's a cupless event with chip timing, organized by volunteers to benefit local conservation groups. Runners should be prepared fo..

The Lake Mohegan Women's Trail Race is a women's-only trail event in Fairfield, CT. Runners can choose from a 5K, 10K, or a 4-hour challenge on the runnable trails around the lake. The event aims to welcome both newcomers and experienced tr..

This 50k trail run connects Connecticut's technical Regicides and Quinnipiac Trails. The challenging out-and-back course features significant climbing and a strict 10-hour cutoff. The event does not allow pacers or crews and enforces interm..

Trail races in Lyme, Connecticut offering a 9.2 mile loop and a 3 mile sprint on Mount Archer trails. Chip timed and rain or shine, with 100% of proceeds donated to local emergency services.

A dual-event day featuring a Family Color Run and a 5K Trail Run on May 9, 2026, in Hamden, CT. The first 100 to pre-register get a special giveaway, with water stations available for all participants.

Experience the Spring Fling 600 trail event featuring a 6 mile race and the 600 distance. This competition serves as a qualifying race for the Anchor Down Ultra and takes place on beautiful woodland trails.

Two trail races, a new half marathon and a 6k sampler, weave through the scenic Shenipsit State Forest past the Soapstone Mountain tower. The event supports local trail stewardship. A cupless race, it's organized by the nonprofit Shenipsit..

Run a 3.5-mile trail race in Wolcott, CT. The event supports the local cross country teams. Your entry includes access to the CT Food Truck Battles Festival afterward.

Test yourself on a challenging and scenic Connecticut half marathon. The course winds past farms and over historic bridges, finishing at a local distillery. Enjoy a post race celebration with food, drinks, and music.

Experience a timed 5K trail race through the scenic meadows and woods of Coogan Farm in Mystic. Enjoy post race festivities with animal ambassadors and support local environmental conservation at this inaugural event.

Event Overview The IronHike Endurance Series - Spring is a multi-day trail endurance event taking place from June 4 to 7, 2026 at Mohawk Mountain Ski Area in Cornwall, Connecticut. It features a FlexRelay format where participants can tackl..

A community 5K trail run, walk and hike in Eisenhower Park Milford on June 7, 2026 supporting the Milford Rotary and the Beth El Center. The course uses a high school cross country route with mostly flat sections and some rolling hills.

Explore the trails of Mansfield Hollow State Park at the Nipmuck South Trail Race. Choose between a scenic 15 mile out and back route or a new, challenging 5K course. Proceeds support local trail stewardship organizations in Connecticut.

Celebrate the longest day of the year with a trail run in Hebron, Connecticut. This event on June 20, 2026, features three distance options on the trails. Choose from a 3 mile, 5 mile, or 8 mile course.