Trail Running calendar near Woodbury 2025-2026

Tackle an Everesting relay across 61+ miles and 29,029 feet of climbing at Mohawk Mountain in Cornwall CT, with a 72 hour window to run, hike or walk. Team up and test endurance on this epic fall challenge.

Take on a 24 hour trail challenge at Mohawk Mountain with a 28 plus mile course and huge elevation gain that rewards grit and strategy. Run, hike, or walk solo or as a relay with veteran owned IronHike Endurance Productions.

Tackle a scenic 5K or 8K through Pindar Vineyards on flat packed trails while supporting the NY Cancer Foundation. Finish with live music, food trucks and a complimentary glass of Pindar wine for a festive fall celebration.

Conquer Mohawk Mountain on scenic but rugged trail courses with 5K, 10K, half marathon and marathon options, big climbs and singletrack. Runners earn finisher medals, enjoy aid stations and follow a cupless policy to reduce waste.

Paine to Pain Trail Half Marathon offers a scenic single loop through five Westchester parks, with 90 percent on dirt trails, roots and rocks under tree cover. Expect abundant wildlife, quiet forest passages and a true trail running challen..

Join the Suffolk County Marathon weekend in Bay Shore NY on Oct 17 and 18, 2026, with races from a kids 1K to the full marathon plus a virtual challenge you can complete anytime. Fun for families and serious runners alike.

Tackle rugged trails at Big Bear SquaTCh South, a half marathon and 10K in Harriman State Park with steep climbs, roots and a short scramble. Small field and proceeds benefit trail maintenance for an intimate, rewarding race.

Join the Clinton Road Zombie Run on Oct 18 in West Milford NJ, from a spooky Zombie Crawl to a 10k through foggy woods with volunteer zombies and haunted aid stations. Finish with music, costumes, survivor medals and prizes.

Run through colorful fall fields at Muscoot Farm on Oct 25 with a scenic 5 mile trail and kids races for the whole family. Finishers get Farm Bucks to spend at the farmers market for a community focused autumn outing.

Fall Back into the Trails is a weekend trail running festival at Red Wing Recreation Area in Lagrangeville NY with 100k, 50k and 10k options. Enjoy full aid, custom finisher medals and awards, and UTMB Index status for the 50k and 100k.

Run the Vineyards Unionville offers scenic 5K and 8K trail runs through vineyards with chip timing. Enjoy live music, food trucks, a souvenir stemless wine glass and a post race pour for a festive finish.

Run or walk the family friendly Never Stop Running Foundation Long Island Turkey Trail Trot, a scenic 5K through Bethpage State Park on November 14, 2026. Enjoy post race refreshments and a festive community atmosphere.

Tackle a scenic 13.1 mile trail half in Roosevelt Forest, eight laps of a 1.64 mile wooded loop with roots, rocks and rolling hills. Costumes are encouraged with prizes, plus a book drive to benefit local kids.

Join FEAR Trail Fest 2026 for a scenic, technical 5 mile loop at Lewis Morris Park in Morristown, NJ with rocks, roots and about 600 feet of climbing. Registration opens May 31 2026 and is limited to 120 runners, hikers welcome.

Join a scenic 3.5 mile Thanksgiving trail run or walk around Scoville Reservoir in Wolcott CT on November 26, 2026 to benefit the Endometriosis Foundation of America. Enjoy post race yoga, finisher medals, swag and a dog friendly vibe.

Join the Inwood Hill Turkey Trot, a festive 5K through scenic Inwood Hill Park on Thanksgiving Day. Run or walk to support the Inwood Food Pantry while enjoying community spirit, free finish photos, and live results.

The NSRF Leftover Turkey Trot 5K will take place in Bethpage on Saturday 28 November 2026. You can run 5 kilometers.

The NSRF 50/50 Turkey Trot 5K will take place in West Babylon on Sunday 29 November 2026. You can run 5 kilometers.