Trail Running calendar near New Shoreham 2026-2027

A memorial 5k trail run and walk in Kingston, MA on March 14, 2026 that raises funds for a scholarship established by the participant's family. First fifty entries receive a t-shirt and all proceeds support the scholarship.

Run or walk through 50 acres of beautiful vineyards in Peconic for a chip timed 5K event. Participants receive a finisher medal that doubles as a wine stopper and a celebratory pour of wine at the finish line.

A Trail Animals trail event at Hale Education in Westwood offering a timed six hour option and a 3.5 mile singleloop on mostly singletrack around ponds. One cupless aid station at start/finish and limited parking with possible walking.

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.

The Brookhaven Trail 15K and 4 Mile runs explore the varied paths of Brookhaven State Park. This cupless event is capped at 250 runners and includes awards, refreshments, and supports veterans and local food banks.

Experience three seasons of trail running and walking through scenic conservation land and a working vegetable farm in Wrentham with this unique 5K triple series.

The Radish Rambler 5k is a trail run, walk, or hike through scenic conservation land and White Barn Farm in Wrentham. Held on April 25, 2026, it kicks off the farm's season and the Farm to Trail Series. Proceeds support local agriculture an..

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.

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..

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..

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.