Trail Running calendar near Burlington 2025-2026

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.

Take on a scenic 5 mile trail run through Muscoot Farm in Katonah on Oct 25 with kids races for young runners. Cross the finish to collect Farm Bucks to spend at the Muscoot Farmer's Market and enjoy a festive community atmosphere.

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 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 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.

Join a scenic trail 5K at Bethpage State Park on November 29, rain or shine, with a free kiddie dash. Proceeds benefit the Never Stop Running Foundation and finishers enjoy shirts, refreshments, and live results.

Join a scenic 5K trail run at Belmont Lake State Park with refreshing postrace snacks and a 50/50 raffle offering cash prizes to winners who are present. Proceeds support the Never Stop Running Foundation.