Trail Running calendar near Ashford 2026-2027

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.

A recurring, in-person group trail run for women and nonbinary people around the North Reservoir in Winchester, MA, covering a conversational 3 mile loop at about 11 to 12 minutes per mile. Sessions are led by local run leaders and cancel f..

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 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 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 second annual trail event in Dunstable, Massachusetts offering a 5 mile loop or a six hour race of repeated 5 mile loops. The course follows an old railroad bed, an arched stone bridge, woods, peaks, and single track trails.

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 low key trail event in Ashfield, MA on June 13, 2026 that showcases local trails and preserved lands. It offers 50 km, 30 km and 10 km distances and raises funds for the Franklin Land Trust.

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.

A trail 5K and 10K at Pleasant Valley Wildlife Sanctuary on June 13, 2026, with routes on single track trails and carriage roads. Proceeds support Mass Audubon conservation; water stations, finish area refreshments, and limited parking.

A mixed-surface 5 km race and one-mile fun run at Hampshire Regional High School in Westhampton on June 13, 2026. The 5 km combines paved roads and wooded trails; awards, refreshments, restrooms and parking are provided.