Trail Running calendar near Sterling 2026-2027

A memorial 5K run and walk at Owen Bell Park in Dayville CT that raises funds for a scholarship for Killingly Ag-Ed seniors. The day includes a 5K, a walk, and a kids fun run on off-road paths with possible trip hazards.

A 12 hour loop race in Lawrence Woods, Middlesex Fells Reservation on July 18, 2026. Runners follow a 4.24 mile technical loop with about 410 ft gain per lap and use a Bring Your Own Everything support approach with minimal aid.

A 1 mile out and back on the Farmington Canal Heritage Trail with a crushed gravel surface and hand timing. Held July 19, 2026 in East Granby in two waves with limited parking; proceeds benefit charities.

A 5.5 mile mountain trail race at Soapstone Mountain in Somers CT organized by Shenipsit Striders. The course features six ascents, steep rocky sections, a field capped at 50 runners, and required online registration.

Muddy Dash Boston is a family-friendly 5K mud run at 508 INTL Adventure Sports Center on August 1, 2026, with obstacles, mud pits and slides, plus a pre-party and an after-party with music and food.

A 7-mile USATF sanctioned trail race in Barkhamsted, CT on 08/01/2026. Registration runs 05/03/2026 to 07/31/2026 with a $20 fee and no race day registration; results posted online by Greystone Electronics.

A community cross country meet at Stonington High School offering a 5K and a children's 1/2 mile. The course mixes track, quiet campus streets, trails, grass, and finishes back on the track.

A community fundraising day in Groton, MA on August 5, 2026 featuring an 8.4 mile three-person relay, kids single-loop race and Little Lambs mini runs, followed by barbecue and activities, with proceeds to six local charities.

A four mile beach run at low tide on Nantasket Beach in Hull, Massachusetts. The out and back course starts near the Mary Jeanette Murray Bath House and raises funds for Hull Boosters and The Emma Ryan Memorial Fund.

A seaside set of timed ultra-marathon events at Colt State Park in Bristol, Rhode Island, offering 6 hour, 12 hour, and 24 hour formats with separate entry periods and fees.

A trail event at Noon Hill Reservation in Medfield offering a 10 mile loop plus 50K and 40 mile ultra options, mostly singletrack with roots, rocks, and a scenic Noon Hill vista; proceeds benefit The Trustees of Reservations.

A scenic 2.5 mile trail run and walk at Wildwood State Park on August 8, 2026 with online registration, personalized bibs if requested three weeks ahead, and proceeds benefiting the Friends of Wildwood State Park.

A multi day timed trail event on a Winchendon farm using a roughly two mile loop. Runners choose from six hour day or night, 12 hour, 24 hour, or 48 hour formats under the Sturgeon Moon.

A free eight hour trail event in Tolland on August 15, 2026 where runners complete as many 3 mile loops as they wish. The event includes on-site food, a potluck, and a GPX course map.

A 5K off-road trail run, walk, and hike at White Barn Farm through Wrentham conservation land. The event is part of the Farm to Trail 5K Series and raises funds to support local agriculture and food pantry donations.

Experience a community trail run through Elm Ridge Park benefiting the Rocky Hill Fire Department and Library. This event features a two loop trail course for adults and a fun medal race for kids.

A chip-timed 5K run/walk at Brimfield Winery on a two-lap grass course with hills, race swag, a wine pour, and age group awards; a one-lap 1.5 mile division is available.

A 5K cross country race at Waters Farm in Sutton Massachusetts that opens the USATF New England XC Grand Prix series. Separate men's and women's open races, on site registration, and a post race awards ceremony.

Ocean State Ultra in West Greenwich, Rhode Island (August 29–30, 2026) offers a 100 mile race with a 34 hour limit plus 12 and 6 hour loop events; registration runs March 30 to August 17, 2026.

An inclusive trail festival at Northfield Mountain on August 29, 2026 that centers queer and trans runners and allies. It offers a 20k prediction race, an untimed 5k fun run or hike, and a Kid's Run with community-focused prizes.