Trail Running calendar near Wading River 2026-2027

Hit the trails at South Mountain Reservation on January 10, 2026 for NJ Trail Series SOMO Winter 3, with 5K, 10K and 13.1 mile looped courses over hills and single track. Aid stations, on site registration and a giveaway add winter race day..

Take on rugged singletrack and carriage roads at the Frosty Fat Sass, a winter trail running and hiking event in West Orange's South Mountain Reservation. Choose a 5K loop or timed 3 hour and 6 hour options while supporting the South Mounta..

Join the Frozen Heart 900, a free grassroots winter loop in Rockfall CT where runners take on a 15 hour challenge around a 2.2 mile trail loop. Self supported format with a heated meeting room for warming, so bring headlamps and carpool.

Join the Squatchy Onesiefest 5K on Feb 14 in Mahwah NJ for a playful, flat 5K around Scarlet Oak Pond or a shorter fun run. Costume lovers earn awards for top finishers in onesies, with on trail aid and a cozy race village.

Run the Febapple Frozen in South Mountain Reservation, South Orange NJ, where four trail distances loop around a scenic 10 mile course in late February. Expect winter trails, aid stations, swag and timing for a hearty challenge.

Squatchapple is a scenic trail race at South Mountain Reservation in West Orange, NJ, with distances from 11 to 50 miles across three challenging loops. All finishers get a handcrafted wood medal and one shop item.

Enjoy a 34 mile point to point run along the scenic Lenape Trail, riding the train to the eastern start and finishing back at your car. Self supported with varied surfaces and skyline views, the route winds through parks, neighborhoods and..

Run the 4 Leaf Clover 5K at Bethpage State Park on March 8, 2026. Enjoy scenic soft trails, a free kiddie Clover run and a one week virtual 5K, plus a themed shirt while supporting the Never Stop Running Foundation.

Run a chip timed 5k through Osprey's Dominion vineyards on a scenic two lap loop suitable for runners and walkers. Includes a tee, shatterproof wine glass, a finisher medal that doubles as a wine stopper and a pour of wine.

Tackle roughly 16 miles on the scenic, technical Nipmuck Trail in Union, Connecticut, running an out and back through Yale Myers Forest to Boston Hollow. Field capped at 100 with limited aid and no race day registration; proceeds support lo..

Run the 34 mile Lenape Trail from Branch Brook Park to South Mountain Reservation, passing parks and varied terrain, while supporting clean water projects. Solo runners get full crew support or join a 3 to 6 person relay.

Run Sleeping Giant State Park on scenic, challenging trails with 25K and 50K options. Tackle runnable miles, rocky singletrack and a steep scramble to sweeping views, while supporting the park through registration proceeds.

Explore rugged North Jersey wilderness in The Fools Adventure, a 10 hour foot ROGAINE with over 100 checkpoints across scenic, rocky terrain. Test your map and compass skills as you navigate for the best route and enjoy big views.

Tackle a rugged, technical 10k through Van Cortlandt Park in the Bronx on March 29, 2026, and grab a commemorative souvenir. A portion of entry fees supports the Van Cortlandt Park Alliance for trail upkeep and youth programs.

Run rugged, technical trails at Bear Mountain with 10K or half marathon options and stunning Hudson Valley and NYC skyline views. Proceeds support the New York New Jersey Trail Conference; race day is Apr 4.

Join the Spring SOMO Timed Trail Races on April 4, 2026 in South Orange, NJ for looped trail fun at South Mountain Reservation. Pick a one or two loop race or challenge yourself in one, three, or six hour timed events on a 1.88 mile loop.

Enjoy the Bunny Trail 5K at Bethpage State Park, starting on a polo field and winding along soft, flat trails. Family friendly with a kiddie run, virtual option, refreshments, and proceeds benefiting the Never Stop Running Foundation.

Run a scenic quarter marathon at West Hartford Reservoir on April 11, 2026, as the Hartford Track Club hosts a small, timed field limited to 150 runners. Enjoy chip timing, post race treats and a friendly, looped trail course.

Join the Run for the Rescue 5K trail run or walk on April 11, 2026 at Blydenburgh County Park in Smithtown, NY, and support Last Chance Animal Rescue. Enjoy scenic trails, dog friendly fun, and optional virtual participation rain or shine.

Run or walk the John Jay Community Trail Race in Cross River through scenic wooded trails and rolling hills, with 5k, 4k walk and a Kids Jay Dash on the track. A family friendly community event that finishes on the John Jay Contest Field.