Trail Running calendar near Charlestown 2026-2027

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 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.

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.

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 20 mile single-loop hike through Wompatuck State Park near Boston on June 6, 2026, with aid stations roughly every 5 to 7 miles, finisher medals and certificates. The event is currently sold out.

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 Long Island on June 7, 2026, held at Dorothy P. Flint 4-H Camp. The course features more than 18 obstacles and welcomes participants aged seven and older in a non competitive, team focused setting.

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 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.

A loop based endurance race near Big River Management Area in West Greenwich, RI where runners must complete each circuit within 60 minutes to continue; laps repeat at one hour intervals until only one runner remains.

Trail races in Mansfield Hollow State Park offering a 15.7 mile out-and-back on the Nipmuck Trail and a new in-park 5K, with varied terrain, marked courses, and proceeds benefiting Connecticut trail stewardship groups.

A community 5K trail run, walk, and hike at Eisenhower Park in Milford on June 14, 2026, on a high school cross country course. The event supports the Milford Rotary and Beth El Center and includes music, water, snacks, awards, and T shirts..

A community run on a three-loop course at the Natick Community Organic Farm, mixing trail, field, and road surfaces. Participants receive a commemorative chicken medal and top finishers are tracked in adult and kid categories.

A morning trail run at Gay City State Park on June 20, 2026, offering 8 mile, 5 mile and 3 mile races. The 8 mile joins regional trail series and includes team competition with prize money.

Three summer trail races at West Hill Dam in Uxbridge, MA, with well-marked wooded single and double-track courses, limited fields, age-group prizes, and a portion of fees donated to local food pantries.

Test your endurance at Roosevelt Forest on a 2.1 mile loop featuring classic New England terrain. Complete as many laps as you wish over 33 hours or aim for the 100 mile buckle in this intimate 50 runner event.