Trail Running calendar near Southwick 2026-2027

Run a 3.5-mile trail race in Wolcott, CT. The event supports the local cross country teams. Your entry includes access to the CT Food Truck Battles Festival afterward.

Join this adventure based event in Barrington featuring a 1.5 mile neighborhood loop and an accessible adaptive course. This family focused run includes electronic timing and performance shirts for the first 1,000 participants.

A trail race in Keene NH on May 23, 2026 using a 12.5k loop system with options up to 50K. The unpaved course features technical single track, jeep roads, cupless aid stations, drop bags, and parking at Fuller Elementary.

Mine Hill Half Marathon is a 13.1 mile road race in Roxbury, Connecticut, with start and finish at Mine Hill Distillery. The course passes farms, fields and scenic vistas and includes a post-race gathering at the distillery.

Experience a scenic trail race through the historic Powisset Farm and Noanet Woodlands. Choose from four distances featuring grassy farm paths and forested trails including a climb up Noanet Peak.

Operation Mohawk Tactical 2 unites the Mohawks Medevac and Honor & Remember 5 Miler events. It takes place at F Gilbert State Forest in Foxboro, supporting veteran and first responder suicide prevention. Participants can run, ruck, walk, or..

Experience a 5K cross country run or walk through the mowed trails of Peach Hill Park. Reach the highest point in Poughkeepsie for panoramic views and enjoy post race snacks and awards.

Experience a timed 5K trail race through the scenic meadows and woods of Coogan Farm in Mystic. Enjoy post race festivities with animal ambassadors and support local environmental conservation at this inaugural event.

Test your skill and grit at a permanent outdoor obstacle facility in Wallkill. Explore a variety of competitive sprints and non-competitive endurance courses for both adults and children over a two-day weekend.

Test your limits at this multi day vertical endurance series at Mohawk Mountain. Choose from seven elevation based challenges ranging from 12 to 84 hours as an individual or part of a flexible relay team.

A point-to-point trail event on the New England Trail offering 112-mile and 50-mile options. Entrants must donate to the Connecticut Forest and Parks Association and provide proof; runners must self-navigate and arrange crew support.

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.

Run a flat, out-and-back course on the scenic Holliston Rail Trail. This event offers a 5K and a 10K for adults, plus a fun run for kids with distances based on age. The community gathering point is Blair Square in Holliston.

Experience an empowering 5k obstacle mud run designed for women at Dorothy P. Flint 4-H Camp. Support sisterhood and breast cancer awareness while navigating a fun and muddy course in Riverhead.

A five mile fun run along the Cheshire Rail Trail from the Fitzwilliam Railroad Depot to the restored Troy Depot, with a short children's loop and food and festivities at both depots. The event raises funds for local historical societies.

Experience a 5K trail and obstacle run featuring 24 challenges across a 400 acre campus in Wallingford. This inclusive community event supports adaptive sports programs through a mix of wooded trails and open fields.

Experience a scenic New England trail event in Dunstable with a 5 mile loop or a 6 hour timed challenge. Support the Humane Society while running through historic quarries and former ski hills.

Explore the hill towns of western Massachusetts on a mix of trails and dirt roads. Choose from a 50k, 30k, or 10k distance, with all proceeds supporting the Franklin Land Trust's conservation efforts at the scenic Edge Hill Conservation Are..

Trail races at Mansfield Hollow State Park: a ~15.7-mile out-and-back on the Nipmuck Trail and a new 5K inside the park, with proceeds supporting Connecticut trail stewardship and organized by the Shenipsit Striders.

A community 5K trail run, walk and hike in Eisenhower Park Milford on June 7, 2026 supporting the Milford Rotary and the Beth El Center. The course uses a high school cross country route with mostly flat sections and some rolling hills.