Trail Running calendar near Pawcatuck 2026-2027

Explore the trails at the scenic Frances A. Crane Wildlife Management Area. Choose your challenge with 10K, 20K, or 30K looped courses. This event supports local conservation and community wellness initiatives.

The Watuppa Trail Races offer a fast and flowy course through the scenic Watuppa Reservation. Choose from three distances: a 10K, 30K, or 50K. The event is known for its community feel and welcoming finish line.

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 varied landscapes of Block Island with a 10K course featuring coastal tracks and rolling pastures. Running through diverse terrain this spring event includes a steep double tiered climb and views of the Atlantic.

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.

Run a unique 4K trail race on Cathleen Stone Island in Boston Harbor, accessed by a short ferry ride. The two-day event supports free science education for local youth and features a post-race party. Choose to run individually or with a cor..

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.

This spring trail run on May 25, 2026, takes you through the scenic paths of Powisset Farm and Noanet Woodlands in Dover, MA. Choose from four distances, from 1.5 to 8.6 miles, in this cupless race. It's part of a farm-based series with awa..

Overview The Connecticut Ultra Traverse (CUT) is a point-to-point trail running event with two distances. The CUT112 is a 112 mile run following the Blue Blazes of the New England Trail (NET) from the Massachusetts-Connecticut border to the..

Run a flat, out-and-back course on the scenic Holliston Rail Trail. This event offers a 5K and a 10K for adults, plus a fun run for kids with distances based on age. The community gathering point is Blair Square in Holliston.

Run a scenic 3-mile trail through vineyards and farms at Westport Rivers Winery. After the race, enjoy a dinner with wine and live music. All runners receive a souvenir wine glass.

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.

Test your endurance on a 4.25-mile loop in Hamden, CT. Set a goal from a marathon to 50 miles within the 12-hour window. Your registration supports local trail maintenance and comes with unique swag.

The TARC Blue Hills Skyline Trail Run will take place in Canton on Saturday 11 July 2026. You can run 12 kilometers.

A unique trail race at Soapstone Mountain featuring six ascents. Runners circle the base and climb each upward trail they find, finishing with the infamous Killer Hill. The challenging course includes rocky and steep terrain.

An evening cross-country event at Stonington High School on August 5, 2026, featuring a 5K and a Children's 1/2 Mile for ages 10 and under. The course starts and finishes on the track and includes campus streets, trails, grass, and a bridge..

The Tarc Summer Classic will take place in Medfield on Saturday 8 August 2026. You can run between 10 and 40 miles.