Trail Running calendar near Kingston 2026-2027

Join a friendly, informal 5 to 10k run or snowshoe on a roughly 10k course with loaner snowshoes available. Bring a spare pair to share, enjoy light refreshments, and team up for bragging rights and a shared baked treat.

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.

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.

A late-winter trail run at Gilbert Lake State Park offering 50K, 25K, and 10K on a marked 6-mile loop with aid at a lakeside cabin and proceeds supporting The Neighborhood Center.

Run or hike scenic woodland trails at Mahlon Dickerson Reservation in the Mahlon Winter Donut Run and Hike, with 5 or 10 mile options. All weather welcome and finishers receive a long sleeve shirt, medal and donuts.

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.

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.

Join the Morris County Empanada Trail on March 29 in Morris Plains NJ with 5K and 10K runs over scenic mixed terrain. Entry includes a long sleeve shirt, finisher medal and an empanada with proceeds benefiting the Arthritis Foundation.

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.

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.

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.

Run a scenic all terrain 5K through Stamford Museum and Nature Center, looping Bendel Pond and passing farm animals. Bring kids for a fun run with Petunia the Scottish Highland cow and support the museum.

Take on the Traprock 50 at Penwood State Park in Bloomfield, CT on April 18, 2026. Choose a rugged 50K of three rolling, rocky loops or a single 17K loop along technical single track and scenic forest roads. Bring your own cup.

Join the final Conquer The Trail Race on April 18 in Dobbs Ferry at Mercy University for a scenic 7.5k on the Croton Aqueduct Trail. Celebrate Mercy's 75th, snag a commemorative shirt, and support the Mav Market.

Join the Brooklyn Cider House Spiked Apple 5K in New Paltz on April 19, 2026 for a chip timed run or walk. Enjoy a tee, cider pour, donut and a finisher medal that doubles as a bottle opener for a festive post race celebration.

Join the 10K Run for the Osprey at Lacawac Sanctuary on Sunday April 19 2026, with a scenic 10K trail run and a family friendly 5K walk supporting sanctuary conservation. Expect wooded trails, osprey sightings, and awards for top finishers.