Trail Running calendar near Spuyten Duyvil 2025-2026

Join the Darien Depot Overstuffed Turkey Trot at Darien High School on Nov 28 for 5K, 1 mile and kids races on scenic cross country trails, with medals for all finishers. Proceeds support The Depot youth center and post race music and food.

Run a scenic 5K at Bethpage State Park with the Never Stop Running Foundation Leftover Turkey Trot, offering in person and virtual options. Free kiddie dash with ribbons and proceeds support the foundation.

Squatchy Leftovers is a scenic trail festival on November 29, 2025 at South Mountain Reservation in West Orange NJ, with distances from a 50K to a kids mile on a rugged 5K loop. Expect technical singletrack, handcrafted wood medals and a ch..

Join the Never Stop Running Foundation 50/50 Turkey Trot, a scenic trail 5K at Belmont Lake State Park on November 30. Half of net proceeds are raffled to participants with winners present and the rest supports the foundation.

Take on a crisp late November trail at Stillwell Woods Preserve in Woodbury on November 30, 2025. Rob's Trail Run Edition features a scenic 5K with separate adult and high school youth divisions for runners of all levels.

The Santa's Summit 10k is a scenic and challenging trail run held at Bull Run Marina in Clifton, Virginia. The course follows the Bull Run Occoquan Trail, featuring hilly terrain with a mix of out-and-back and one-way sections. Participants..

Join the Winter Wonder Run 6K through the scenic trails of Institute Woods in Princeton on Saturday December 6, 2025. Enjoy a crisp cross country course with limited field size for a cozy, community race.

Join the Tower Tag Challenge at Sleeping Giant State Park for a scenic timed loop to the Observation Tower, with 4 hour and 8 hour options. Run repeated 3.3 mile laps on a smooth carriage road with aid station support and finisher medals.

Run a timed 50 miles or 50 kilometers in Prospect Park on a scenic looped course near Lincoln Road. Community aid with Skratch Labs hydration and a potluck style aid station keeps you fueled across the day.

Tough Cookie 8K at Sunken Meadow State Park offers scenic cliffside views of the Long Island Sound, festive cookie stops and a post race cookie fest. All paces welcome and proceeds support local charities.

Challenge yourself at the Holmdel Classic, a scenic but hilly loop trail race in Holmdel Park with roots, rocks and steep climbs and options from a single 4.65 mile lap to multi loop ultras. Proceeds benefit MissionCleanWater.

Take on SRC Presents: A Backyard Ultra on Dec 13 to 14, 2025 at Blydenburgh Park, where runners do 4.167 mile laps each hour until one remains. A 1 Lapper runs alongside and proceeds benefit the Long Island Greenbelt Trail Conference.

Join the NJ Trail Series SOMO Winter 2 on Saturday December 13 in South Orange for scenic looped trail races through South Mountain Reservation. Choose 5K, 10K or 13.1 mile and enjoy hilly single track, a giveaway and day of registration.

Run the Frosty Forest 5K in Stratford through Roosevelt Forest on an off road trail welcoming runners, joggers and walkers. Holiday costumes encouraged, every finisher gets a commemorative item and proceeds support local charities.

Join the 8th Annual Taco Trials in Rocky Hill: eat a taco then run a 1 mile loop, repeating it ten times for a fun, quirky challenge. Medals for finishers and proceeds benefit the Connecticut Forest and Park Association.

Run the Last Supper 100k in Roxbury NJ on Dec 27, starting at Horseshoe Lake. Choose solo or relay teams up to 10 and tackle scenic trails and lakeside roads for a winter ultramarathon adventure.

Join the West Rock Winter Fat Ass in Hamden CT on Dec 28, 2025 for eight hour loop fun around Lake Wintergreen. Run repeated 1.6 mile laps with aid and snacks in a 50 runner field while supporting Make a Wish and the American Cancer Society..

Join the Frosty Fat Sass on Jan 31 in West Orange for a rugged trail fat ass fundraiser supporting South Mountain Conservancy. Choose a 5K, or timed 3 hour or 6 hour loop challenge with a rucking division and enjoy technical winter trails.

Try snowshoe racing at Mountain Creek on January 31, 2026 with a scenic ridge 5k or a relaxed one mile finish. Ride the lift to the top, bring your own snowshoes, and enjoy a fun winter run for all abilities.

Dress in your best onesie and tackle scenic trails at Squatchy Onesiefest in Ramapo Valley. Choose a fun 1.6 mile loop or a two lap 5K, enjoy trail support and a handcrafted finisher medal while supporting the NY NJ Trail Conference.