Trail Running calendar near Kingston 2025-2026

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.

Join the ninth annual Frosty Fat Sass at South Mountain Reservation, a fundraiser for the South Mountain Conservancy. Choose a 5K, timed 3 or 6 hour loop or rucking division on a rugged, rocky 5K trail.

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.

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.

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.

Squatchy Onesiefest 5K at Ramapo Valley is a festive trail run with a handcrafted finisher medal and awards for onesie wearers. Limited to 200, the flat gravel loop welcomes road shoes and offers aid and parking.

Fire and Ice Winter Run, Feb 21 2026 at Gilbert Lake State Park, offers 50k, 25k and 10k on scenic looped trails and is snowshoe friendly. Warm aid, a finisher mug, special awards and proceeds benefit The Neighborhood Center.

Run or hike rugged woodland trails at the Mahlon Winter Donut Trail Run and Hike, with 5 and 10 mile options around Saffin's Pond. Trail markers keep you on course and the event runs rain, snow, or shine for a true winter adventure.

Squatchapple puts scenic singletrack and carriage road loops in South Mountain Reservation to the test with distances from 11 miles to 50 miles. Support the South Mountain Conservancy and earn a handcrafted wood medal and race swag.

Tackle rugged singletrack and steep rock scrambles at the Sleeping Giant Trail Runs in Hamden CT on March 29, 2026. Choose a challenging 25K loop or a double 50K and enjoy aid stations, medals and post race food and drinks.

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 technical, rugged trails and steep climbs at Big Bear Squatch North in Bear Mountain NY on April 4, 2026. Choose a challenging 10K or a grueling half marathon, with proceeds supporting the New York New Jersey Trail Conference.

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 John Jay Community Trail Race in Cross River NY on Sunday April 12, 2026 for a family friendly outing with a 5k, 4k Jay Walk and a 200 meter Kids Dash. Race on scenic wooded, hilly school trails and finish at the track.

Tackle wooded trails at the Farm & Forest All Terrain 5K and Hog Wild Kids Fun Run in Stamford, CT on April 12, 2026. Family friendly and community focused, this race raises funds for the Stamford Museum and Nature Center.

Run the Traprock 50 at Penwood State Park in Bloomfield CT on Apr 18, 2026, choosing 50K or 17K looped courses over technical single track and rocky terrain. Chip timing, cupless aid, and proceeds support local conservation.

Join the final Conquer The Trail Race on April 18 in Dobbs Ferry for a scenic 7.5 km on the Croton Aqueduct Trail supporting Mercy University's Mav Market. Mostly flat trail with natural obstacles, raffles and shirts for early registrants.

Run the Brooklyn Cider House Spiked Apple 5k in New Paltz on April 19, 2026 for a chip timed 5K through cider country. Enjoy a homemade cider donut, a pour of cider and a finisher medal that doubles as a bottle opener.

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.

Squatchywaska Mountainfest in Ellenville offers adventurous 25K and 10 Mile trail runs on the Shawangunk Ridge with steep climbs, technical singletrack, and stunning views. Entry is capped at 150 and proceeds help protect Verkeerder Kill Fa..