Trail Running calendar near Westerly 2026-2027

A community run at Ives Farm hosted by Cheshire Community YMCA and Cheshire Land Trust. Features a trail 5K, a youth Y Cup relay with elementary teams, a free Pumpkin Dash for young children and family fall activities.

A backyard ultramarathon and festival at Waters Farm in Sutton MA where runners complete a 4.167 mile loop each hour on the bell until one remains. The weekend features live music, hay rides, a kids fun run, farm tours, and local food.

A fall trail 5k in Berkley MA combining running, rucking, and walking to honor military, first responders, and K9s. Dogs are allowed on leash with a waiver and proceeds support local canine and service organizations.

A fall trail run at Powisset Farm in Dover, MA with four distances on meadow and woodland trails, a cupless aid station, post race cider donuts and family activities including a barnyard and pumpkin painting.

A fall trail event in Harvard on October 25, 2026 featuring a 5K through orchard and woods plus a 1 mile kids fun run, with age divisions, awards, shirts, and proceeds benefiting the Harvard Conservation Trust.

A 5K Run / Walk and Kids Fun Run at Hallock State Park on October 25, 2026, with a virtual 5K option. Proceeds support the Long Island Greenway and include a post-race wine crawl with vendor specials for participants 21 and over.

A stair climb at Gillette Stadium on October 25, 2026 where participants walk, jog or climb around the lower bowl to music and stadium highlights; net proceeds support Homes for Our Troops building homes for severely injured veterans.

A 10K trail race at Penwood State Park in Bloomfield, CT on November 1, 2026. The rolling loop follows mostly technical single track on the Metacomet, Orange and Yellow trails, has no on course aid station and a three hour cutoff.

A two day obstacle event at Fenway Park in Boston featuring a Stadion 5K with 20 obstacles, a kids race, and spectator access. The course uses stadium features including the Green Monster, clubhouse, and home plate.

Looped trail event at White Barn Farm featuring a clearly marked 3.1 mile loop and a fully stocked aid station. Participants stack laps to reach distances from 5K up to 50K, with each completed loop recorded.

A 5k chip-timed run/walk at Stonington Vineyards on November 8, 2026 featuring a two-lap cross country route through the vines. Registration includes a shirt, collapsible wine glass, finisher medal and a pour of wine.

A trail event in Upton State Forest offering a technical 10.5K loop and a two-lap half marathon, with aid stations, post-race food, and custom trophies for overall winners.

A family friendly run and walk at West Thompson Dam on November 8, 2026 featuring a timed 5K trail run, a 3K untimed walk and a free kids 1/4 mile run; proceeds support local trails, parks and a food pantry.

A November trail race at Burlingame State Park offering 4 mile and 8 mile courses on dirt trails and roads, a required orange garment mandate, post-race food, and age group awards for both distances.

Experience a magical 13.1 mile trail race through the rolling hills of Roosevelt Forest. Complete eight loops of a wooded course while supporting a children's book drive in this unique costume friendly event.

Trail races at YMCA Camp Sloper on a roughly two-mile loop: a 400 minute time-limit event with loop counting and a four mile two-lap race, chip timing, a single aid station, cupless policy, and proceeds to local organizations.

A community Thanksgiving trail event on 11/26/2026 at Mill Pond Way Trail with a 3.5 mile run or walk, chip timing, post race yoga for participants, free water and snacks, and proceeds benefiting endometriosis research.

A ninth annual charity 5K in Roxbury, Connecticut on November 26, 2026, with a 3.1 mile out-and-back course near Everett B. Hurlburt Community Park. Proceeds support local ambulance and scholarship funds and a food pantry collection.

Challenge yourself on the historic Tower Trail at Sleeping Giant State Park. Choose between 4 or 8 hours to complete as many 3.3 mile loops as possible on this scenic gravel path to the Observation Tower.

Experience an exclusive trail run through the scenic Roosevelt Forest in Stratford. This 5K event features a natural off-road course limited to a small group of participants and includes custom finisher medallions.