Trail Running calendar near Vernon 2026-2027

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.

A lap based ultratrail at Chesterfield Gorge with flexible distance options on a rolling dirt road beside the river. Aid includes a water only midway station and a fully stocked turn around station; event supports Hilltown Land Trust.

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.

Point to point trail ultramarathon along the New England Trail with 112 mile and 50 mile options through Connecticut. Entrants must donate to the Connecticut Forest and Park Association and arrange their own crew and navigation 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.

Enjoy a 3 mile trail run through the scenic Westport Rivers Vineyard & Winery followed by a vineyard celebration with dinner, wine, and live music.

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.

On June 7, 2026, Ward Pound Ridge Reservation hosts a half marathon (13.1 miles) and a 10k, both passing the summit where the historic fire tower is being reconstructed. Fundraising supports the Friends of the Fire Tower and accessibility a..

A community event at Stanley Park on June 7, 2026 featuring a 5K trail run or a one mile accessible route. Proceeds support renal medullary carcinoma awareness and related programs.

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 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.

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.

A six hour timed trail run at Ansonia Nature Center in Connecticut, raced on repeated 1.9 mile counterclockwise singletrack loops with about 170 feet of climb per loop. Entry is limited to 69 runners and refunds are not offered.

Trail race options of 50k, 30k and 10k around Edge Hill Conservation Area in Ashfield Massachusetts, run on single track and dirt roads. The event partners with Franklin Land Trust and supports habitat restoration and land conservation.

An elimination-style loop race near Big River Management Area in West Greenwich, RI. Runners must finish each loop in under 60 minutes to continue; laps repeat until one athlete completes one more loop than the next finisher.

Trail races at Mansfield Hollow State Park include a roughly 15.7 mile out and back on the Nipmuck Trail and a new 5K single track loop; proceeds benefit Connecticut trail stewardship and the event is 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.