Trail Running calendar near North Fork 2026-2027

ENDURE is a Last Man Standing running event where participants complete a fixed loop every hour. The last runner standing wins, with a central hub for recovery and community. It's designed for all levels, from seasoned endurance athletes to..

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.

The IronHike Spring Endurance Series is a multi day mountain challenge in Connecticut. Choose from six timed events, from a 12 hour hike to an 84 hour ultra, all with massive elevation gain. Participants can go solo or team up in the unique..

Overview The Connecticut Ultra Traverse (CUT) is a point-to-point trail running event with two distances. The CUT112 is a 112 mile run following the Blue Blazes of the New England Trail (NET) from the Massachusetts-Connecticut border to the..

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.

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.

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.

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.

Explore the trails of Mansfield Hollow State Park at the Nipmuck South Trail Race. Choose between a scenic 15 mile out and back route or a new, challenging 5K course. Proceeds support local trail stewardship organizations in Connecticut.

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.

Celebrate the switch to summer with a trail race through the landscape of Hebron Connecticut. Choose between three different distances for a run through the woods during the solstice.

Experience a 5k race through the grassy steep hills of Belmont Plateau in New York. This charitable event includes a race T shirt with registration and supports local causes through every entry.

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.

Test your endurance on a 4.25-mile loop in Hamden, CT. Set a goal from a marathon to 50 miles within the 12-hour window. Your registration supports local trail maintenance and comes with unique swag.

Experience a unique trail race through the Westmoreland Sanctuary where you choose your own path at the fork. Start and finish at Fox Lane High School for a memorable 5k adventure in Bedford.

The Red Wing Trail Challenge offers 60K, 30K, and 15K distances on a rugged 15K loop in Lagrangeville, NY. The course features mixed terrain and significant elevation gain on each lap. Post-race food and unique finisher awards are provided.

Experience a unique four mile trail race through the historic Forest Park in Queens. Run along naturally carved glacial terrain and pine groves with your dog to support a local animal rescue organization.

Join a community trail run or walk at Owen Bell Park to support the Ryan French Memorial Scholarship Fund. This family friendly event features a 5K trail, a walk, and a free kids fun run.