Trail Running calendar near Sleepy Hollow 2026-2027

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.

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..

Trail races at Red Wing Recreation Area near Lagrangeville NY offering 60K, 30k and 15K on a 15k loop with varied terrain, aid stations, and awards for top finishers and finishers in select distances.

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 point to point 5K in East Hampton that starts at the Connecticut Draft Horse Rescue and finishes at the Old Home Days grounds. Shuttle buses serve the start, pre registration includes a 2026 T shirt and walkers are welcome.

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.

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 midweek evening trail run through the diverse terrain of Bowdoin Park. This 5 mile race features a mix of grass and rocky trails with awards for top finishers and a food drive for the local pantry.

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 unique endurance event at Mount Tammany featuring repetitive loops with significant elevation gain. Participants face escalating weight challenges in a test of physical persistence where only one athlete claims the gold.

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 the wooded trails of the historic Ward Pound Ridge Reservation in New York. This event offers 25K, 50K, and 50 mile distances featuring a mix of technical singletrack and runnable carriage roads.

Honoring September 11 heroes, this arena climb at TD Bank Ballpark features a 2,200 foot track through stadium aisles. Join a timed stair challenge or a flat concourse walk to support the Tunnel to Towers Foundation.

Experience a technical seventeen mile trail run along the Hudson River cliffs with over five thousand feet of elevation change. High endurance is required for this rugged course featuring boulder scrambles and scenic river views.

The Running Wild at Wildwood Trail 2.5 Mile Trail Run/Walk will take place in Wading River on Saturday 8 August 2026. You can run 3 miles.

Experience the technical singletrack trails of Stokes State Forest at this inclusive trail party featuring 5K, 10K, and 17 mile options for runners and hikers of all paces.

A forested 5K on the new trail network at Bridgewater Town Park in Bridgewater, CT on August 9, 2026. The course uses packed dirt and natural paths with gentle hills and views of Lake Lillinonah; participants receive a race-day gift.

Trail races at Fahnestock State Park in Cold Spring NY on August 15, 2026 offer three distances across varied terrain with aid stations, a post race meal, and proceeds supporting land conservation.

Experience the beauty of the Catskill Mountains at this zero carbon event featuring a 25K trail run and an 8K ski slope course. Both distances are open to runners and hikers looking for significant elevation gain and mountain views.

A 6.5 mile trail race at Westmoreland Sanctuary in Mount Kisco on August 23, 2026, with start and finish at the Fox Lane High School campus and a non-perishable food collection for the Mt. Kisco Food Pantry.