Trail Running calendar near Stonington 2026-2027

Join the 20th Wayland / HFC Striders Cross Country Festival on October 11, 2026, featuring youth 3K races and open 5K events that support Wayland High School cross country and track. Presented by Middlesex Savings Bank with awards and commu..

Run or walk through the scenic trails of Blydenburgh Park this autumn. Participants enjoy a 5K trail course complete with seasonal treats and commemorative event swag.

The Wine Run offers a scenic 3-mile trail run through Sakonnet Vineyard. After the run, participants enjoy dinner, wine, and live music on-site. The event also includes non-running dinner options for adults and children.

Experience a point to point trail race in Northeast Connecticut with distances including a marathon, half marathon, 10K, and 5 person relay while supporting local students.

This 3.5-mile trail run/walk on the flat Mill Pond Trail happens in Wolcott, CT. The Wolcott Lions Club hosts the event, which includes a race t-shirt and clam chowder. Registration opens online with a lower early-bird rate.

The Grills Trail Run will take place in Westerly on Saturday 24 October 2026. You can run between 10 and 10 miles.

Run a scenic autumn 5k trail through Wrentham conservation land and a working farm. This cup-less race supports local agriculture and includes family Halloween fun. It's the final event of the Farm to Trail 5K Series.

Experience peak autumn foliage at the Mt. Tom Trail Race featuring a 25k solo or relay, a 10k, and a 5k fun run through rugged Massachusetts state park trails with significant elevation.

Rugged 5k trail run, ruck, or walk in Berkley MA on October 25, 2026 with in person and virtual options. Dogs may join on leash with a waiver and proceeds support The Baystate Beagle Club and Give2Those.org.

This fall trail run takes place at Powisset Farm in Dover, MA, featuring four scenic distances through farm and woodland trails. Post-race cider donuts and family activities like pumpkin painting add to the farm atmosphere. It's part of the..

This 8-hour timed trail run takes place on the rolling farm trails at Gurski Farm in Brookfield, CT. Runners complete as many laps as possible on a course featuring single track. It offers a community atmosphere where participants frequentl..

A trail race at Burlingame State Park in Charlestown on November 15, 2026, offering 4-mile and 8-mile courses around Watchaug Pond. It is the first race in the WTAC fall trail series with multi-race registration discounts.

Run a storybook-themed half marathon on the trails of Roosevelt Forest in Connecticut. The course is an eight-loop journey through the woods, and costumes are encouraged. A book drive is also part of the event, supporting local children.

A Thanksgiving morning trail run supporting endometriosis research. Choose a run or walk on the 3.5-mile Mill Pond Trail, followed by complimentary yoga. All participants get a finisher medal and swag bag.

The Tower Tag Challenge is a timed trail run in Connecticut's Sleeping Giant State Park. Runners complete 3.4-mile laps up and down the scenic Tower Trail within an 8-hour or 4-hour window. The event features awards, post-race refreshments,..

Run through Roosevelt Forest on a festive 5k trail course in Stratford. All finishers receive a custom medallion, and top runners earn awards. Holiday costumes are welcome for this charitable event.

Experience a winter trail challenge at Hale Education featuring 15 mile and 30 hour options. Navigate three unique loops through the Massachusetts woods while testing your endurance and self reliance in cold weather conditions.