Trail Running calendar near Highland Lakes 2026-2027

Experience obstacle course racing at the historic home of the 1969 Woodstock festival. Tackle forest trails and rolling hills in upstate New York with race distances ranging from a 5K Sprint to a 10K Super.

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.

A free, timed 5K trail run at Crystal Lake Park on June 6, 2026, with a technical course of about 300 feet of elevation gain and a 40-runner field limit. Awards and a midway water station are provided.

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 mountain running event in Roxbury, NY on June 7, 2026 featuring a 6.5 mile race with 3,500 feet elevation and a 5k with steep early gain and a downhill finish. Awards go to the top three men and women in each race.

The Run for Woods 5K will take place in Langhorne Manor on Sunday 7 June 2026.

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 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 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.

Experience a unique endurance test at the Wildlands Conservancy South Mountain Preserve featuring a last person standing backyard ultra a nighttime trail lap and a non alcoholic beer mile.

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.

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..

Four Tuesday evenings of cross country racing at Grove 4 in Donaldson Park offering 5k, 2.5k and youth distances. Series and single race entries have tiered fees with member and youth discounts plus post race food and awards.

Manitou's Revenge is a 53 mile ultramarathon in the Catskills with 15,000 feet of gain, technical trails and long self-sufficient sections. The route runs from Windham along the Black Dome Trail and the Long Path to downtown Phoenicia.

Experience fast and flowy singletrack running at the XTERRA Transcend Trail Run in New Jersey. Choose from 5k, 10k, or half marathon distances featuring lakeside views and a world championship qualifying opportunity.

Test your endurance at Elka Park with this 14.5 mile weighted event. Participants navigate over 5,000 feet of elevation gain while carrying a 20 pound pack through the New York landscape.