Trail Running calendar near Yorktown Heights 2025-2026

Run or walk this Thanksgiving on a scenic 5k trail around Scoville Reservoir in Wolcott with medals, swag and timed results. Enjoy pre race stretching and free post race yoga, family and dog friendly, with proceeds supporting EndoFound.

Join the Inwood Hill Turkey Trot, a festive Thanksgiving 5k through scenic Inwood Hill Park in northern Manhattan. Enjoy a family friendly run while supporting the Inwood Food Pantry and celebrating community spirit.

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.

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..

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.

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.

Run or walk the Never Stop Running Foundation Turkey Trot, a scenic trail 5K at Belmont Lake State Park on November 30, 2025, supporting a great cause. Enjoy post race refreshments and a 50 50 raffle with proceeds benefiting the foundation.

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.

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.

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.

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.

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.

Run until only one remains at SRC Presents: A Backyard Ultra in Blydenburgh County Park on December 13 and 14, 2025, looping a rugged 4.167 mile trail. Day and night loops, limited crew access, and proceeds support the Long Island Greenbelt..

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.

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.

Hit the trails at NJ Trail Series SOMO Winter 3 in South Orange with 5K, 10K or a half marathon on looped trails through South Mountain Reservation. Enjoy rolling hills, single track and fire roads, friendly aid stations and a giveaway at t..

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.