Trail Running calendar near Danbury 2026-2027

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.

The Rockwood Ramble 10K offers a scenic run on carriage roads through the woods of Rockefeller State Park Preserve. The event features a standard 10K and a separate kids' run, with all proceeds supporting trail maintenance.

Obstacle course races at Bethel Woods Center for the Arts combine rolling trails, forests, and multiple obstacles across Sprint, Super, and kids formats, with workshops, camping, volunteer options, and spectator access during the weekend.

The Levee Loop Trail Race 10K - Islip will take place in Islip on Saturday 6 June 2026. You can run between 5 and 10 kilometers.

Paired 5K paved loop and 10K mountain trail at Rockland Lake State Park in Valley Cottage, NY. The 5K is a flat, fully accessible lake loop; the 10K climbs about 1,300 ft on rocky, steep terrain and includes one aid station.

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 trail 5K in Shirley Chisholm State Park, Brooklyn on June 7, 2026, organized by Black Men Run NYC. Registration is free with an optional $25 singlet; registration opens March 31 and closes June 4.

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 weekly cross country series offering thirteen 5K races on Tuesday nights from April to July. The event takes place at Central Park in Parsippany and is open to all ages and abilities. Participants can register for the full series or pay f..

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 evening run on a flat paved loop around Rockland Lake. This chip timed half marathon features sunset views, frequent aid stations, and custom finisher medals only 45 minutes north of NYC.

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.

Turf Wars 2026 is a Tone House multi-zone athletic challenge at Chelsea Waterside Park in New York on June 13, 2026. Competitors face three timed zones and a Wild Card in Individual, Doubles, or Team divisions, with medals, prizes, and an a..

A 5K at Van Cortlandt Park with in-person and virtual options, fundraising for new iBE FiT apparel and programs supporting Goodnews To Scholars and the RCCG Tabernacle of Restoration.

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.

A weekly cross country series offering thirteen 5K races on Tuesday nights from April to July. The event takes place at Central Park in Parsippany and is open to all ages and abilities. Participants can register for the full series or pay f..