Trail Running calendar near Islip 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.

Rise of the Obstacles in Wallkill, NY on May 30-31, 2026 features adult and kids obstacle races from a 100 meter sprint to a 2 km multi-lap course, plus a Teddy Bear Crawl nonprofit and a 3D printing fundraiser for youth programs.

Trail race at Tatum Park in Middletown Township, NJ on a repeatable 4.75 mile loop. Distances include 1 lap, 30 km and 50 km and proceeds support MissionCleanWater clean water 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..

Multi-day elevation based endurance events at Mohawk Mountain in Connecticut, June 4 to 7, 2026. Solo, Trail Buddy and Trail Family formats cover timed events from a 12-hour 15-mile option up to 84-hour 152+ miles with large elevation gain.

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 non competitive group run along the D&R Canal Towpath with paced "trains" and multiple distances. The event benefits the Rutgers Cancer Institute with a $0.50 donation per mile and offers bus starts and a picnic option.

A road and trail event at Rockwood Hall in Rockefeller State Park Preserve featuring a 10K and a 1K kids race. The course follows wide carriage roads with Hudson River views and wooded sections, and proceeds support carriage road maintenanc..

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.

A women-only 5K obstacle mud run in Riverhead, NY on June 7, 2026, featuring 18+ obstacles and open to females aged seven and older; participants may run, jog, or walk the course.

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

Trail races at Ward Pound Ridge Reservation on June 7, 2026 include a 13.1 mile half marathon and a 10K, both passing the summit where the historic fire tower is being reconstructed. The event also raises funds for the Friends of the Fire T..

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..

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.

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.

Six hours of looped trail running at Ansonia Nature Center on Saturday June 13, 2026. The course uses roughly 1.9 mile singletrack laps with about 170 feet of elevation gain per lap and is limited to 69 runners.

Turf Wars is Tone House’s multi zone athletic competition at Chelsea Waterside Park in New York where individuals, doubles, and teams complete ten conditioning events across timed zones with a final Wild Card finisher.

The 5th Annual iBE-FiT 5K Invitational at Van Cortlandt Park offers an in-person 5K and a virtual 5K option, a two-loop course with flats and hills, medals for all finishers, and proceeds supporting local community programs.

A community event at Camp Edey on June 13, 2026 featuring a 5K run/walk and a 1 mile family walk, Family Day activities, race amenities, and age-group awards to benefit Girl Scouts of Suffolk County.