Trail Running calendar near Kent 2026-2027

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..

Hit the trails at the YETI OR NOT Snowshoe Invasion at Mountain Creek on January 31, 2026. Ride the lift to the top for a scenic 5k or untimed last mile welcoming runners, walkers and first time snowshoers. Bring your own snowshoes.

The Frozen Heart 900 will take place in Rockfall on Saturday 7 February 2026. You can run 50 miles.

A themed trail event at Ramapo Valley County Reservation with a flat, scenic 1.6 mile lollipop course. Options include a full 5K or a one-loop Fun Run and finishers receive handcrafted medals and aid station support.

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.

Join the Never Stop Running Foundation 4 Leaf Clover 5K at Bethpage State Park, a scenic trail run starting on a grassy polo field. Family friendly with a kiddie fun run, virtual 5K and post race refreshments supporting the foundation.

The Ospreys Dominion Wine Run 5K will take place in North Fork on Saturday 21 March 2026. You can run 5 kilometers.

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 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.

A trail race in Van Cortlandt Park on March 29, 2026, featuring a two-loop 10k and a kids fun run. Prizes include Lloyds Carrot Cake and part of the fees support the Van Cortlandt Park Alliance.

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.

Run the Bunny Trail 5K at Bethpage State Park for a scenic start on the polo field and winding soft trails with a cross country feel. Family friendly with free kiddie run and virtual option, 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 Last Chance's Run for the Rescue, a scenic 5K at Blydenburgh Park on April 11 with virtual entry through Apr 19. Bring leashed dogs, enjoy trails and refreshments, and support Last Chance Animal Rescue.

A USATF certified point to point half marathon in Albany County on April 11, 2026, mostly on paved rail trail with a net downhill and a 500 foot elevation drop to a Hudson River finish. The event offers live tracking, bus to the start, post..

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.

A spring event at the Stamford Museum and Nature Center on April 12 2026 featuring a scenic 5K through farm and woodland and a 0.3 mile kids run past farm animals. Proceeds support the museum and nature center.