Trail Running calendar near Hebron 2026-2027

A weekly 5K trail series at DCR Robinson State Park in Agawam, MA, running Tuesdays from May 26 to August 25, 2026. The course uses rolling double wide and single track trails; onsite registration and a small weekly fee apply.

Operation Mohawk Tactical 2 in Foxboro, MA offers 4, 5, and 9 mile running and rucking options. The event honors fallen service members and supports veteran and first responder suicide prevention under the mission of 22Mohawks.

A timed 5K trail race at Coogan Farm in Mystic, running through meadows, woods, and fields, with limited entry, tiered fees, an awards ceremony, and opportunities to meet Nature Center animal ambassadors.

A choose your own adventure ultra and trail event at Chesterfield Gorge with multiple distances, lap based 50k to 100mi options, a 30 hour window for ultras, and timed 33k and 11k races the following day.

A weekly Tuesday evening cross country series at Waveny Park with varied distances and formats, including predicted time races, relays, handicaps, a luminaria finish, and age-graded awards.

A weekly 5K cross-country trail series at Worthington Winery in Somers, Connecticut, held Wednesdays from June 3 to July 1, 2026. The course runs through backwoods and vineyard areas with views of ponds and a covered bridge.

A multi-day elevation endurance series at Mohawk Mountain in Cornwall Connecticut from June 4 to 7 2026. Events range from a 12 hour 15 mile challenge to 84 hour ultras with solo and team FlexRelay formats.

Point-to-point trail events of 112 miles and 50 miles along the New England Trail in Connecticut. Self-navigation is required, crew support expected, and donations to the Connecticut Forest and Park Association are required for entry.

Experience a timed 5K trail run or walk through the scenic woods and fields of the Van Vleck Farm and Nature Sanctuary. Enjoy live music and food trucks at this annual community event in Woodbury.

A community running event on June 6, 2026 in Holliston with 5K, 10K, and a Kids Fun Run on the flat Holliston Rail Trail. Registration opens March 1; fees are $30 for the 5K and 10K and $5 for the kids run.

A group run on the Ocean State Ultra 10 mile loop in West Greenwich, RI. The route allows runners to turn back early and participants must wear orange because it is hunting season.

A trail run at Westport Rivers Vineyard & Winery on June 7, 2026, covering about 3 miles of mixed trails and finishing among the vines. The event includes dinner, wine, music and a souvenir wine glass, with BBQ only options available.

A women-only 5K obstacle mud run in Riverhead, NY on June 7, 2026, featuring 18+ obstacles and open to females aged seven and older; participants may run, jog, or walk the course.

Trail races at Ward Pound Ridge Reservation on June 7, 2026 include a 13.1 mile half marathon and a 10K, both passing the summit where the historic fire tower is being reconstructed. The event also raises funds for the Friends of the Fire T..

Run for RMC on June 7, 2026 at Stanley Park in Westfield MA offers a 5K trail run and a 1 mile accessible route to raise awareness of renal medullary carcinoma and support related programs.

A free community trail event in Farmington offering shoe demos and short runs on local trails. Options include about 5 km, 1.7 mile, and 1 mile routes, with snacks and drinks afterwards.

A five mile fun run along the Cheshire Rail Trail from Fitzwilliam Depot to the restored Troy Depot on June 13, 2026. The day features food and festivities, a children's loop, return transport on request, and benefits local historical socie..

Experience a day of trail running and mountain biking at the Norbrook Farm Brewery Trail Festival. Enjoy multiple race distances, local food trucks, and rewards at this scenic Connecticut brewery.

A 5K trail and obstacle run on the 400 acre campus of Gaylord Specialty Healthcare in Wallingford CT, featuring 24 obstacles and a festival area with vendors, live music, and food trucks, supporting the Gaylord Sports Association.

A six hour looped trail run at Ansonia Nature Center on roughly 1.9 mile counterclockwise singletrack loops with about 170 feet of gain per loop. Field capped at 69 runners; no crews or pacers; early signup includes a shirt and swag.