Trail Running calendar near Southwick 2026-2027

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.

Fall trail races on rugged single-track at Mt. Tom State Park include a 25k, 2-person 25k relay, 10k and a 5k fun run with significant climbing and proceeds benefiting Kestrel Land Trust.

Experience a unique trail race through the forests and meadows of Muscoot Farm. Enjoy distances for all ages followed by a visit to the local farmers market with your farm buck vouchers.

Tackle a unique mountain course that goes up and down four times over 4.9 miles. The event offers prize money, age group awards, and benefits the Keene Community Kitchen. Early registration includes a t-shirt.

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..

A trail series at Red Wing Recreation Area offering 100k, 50k and 10k on multi-loop courses with notable elevation. The 50k and 100k are UTMB Index races and all finishers receive custom medals.

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 backyard ultra at Kenty's Farm on a 4.1666 mile loop where runners repeat hourly laps until one remains. Timed options of 6, 12 and 24 hours and single-lap entries are also available.

A trail 10k at Ward Pound Ridge Reservation plus a November virtual 100k challenge, with race results, photos, and a custom finisher woodallion for 100k finishers.

Trail races at Tarrywile Park in Danbury offering Marathon, Half Marathon and 10K on technical, hilly single-track with substantial elevation; finisher medals, podium awards and cash bonuses for fast half marathoners.

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.

A 13.1 mile trail race in Roosevelt Forest made up of eight laps of a 1.64 mile wooded loop, featuring on course aid, a book drive with Books4Everyone, costume prizes, participant medallions, and podium awards for top finishers.

Test your endurance at YMCA Camp Sloper with a 400 minute timed challenge or a 4 mile trail race. Explore rolling wooded trails in Southington while supporting local charities and youth running programs.

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.

Trail 5K in Roosevelt Forest, Stratford CT on Dec 19, 2026. Participants can run, jog, hike or walk and may wear holiday costumes; awards go to the three fastest men and women and a portion of proceeds supports local causes.