Trail Running calendar near Highland Lakes 2025-2026

Macedonia Trail Race at Macedonia Brook State Park offers scenic single track and forest trails with climbs and viewpoints. Choose 50K, 25K or 12K for a rewarding day of trail running in Connecticut.

Experience a three day trail running festival at Wawayanda State Park in mid September 2026 with races from a 1 mile kids run to a 100 mile ultra. Free camping and a partnership with Bigger Than The Trail support community and mental health..

Tackle the Hook Mountain Ultra, a rugged multi loop trail outing in Upper Nyack, NY that crowns each circuit with a climb to the Hook Mountain summit. Choose marathon or 50 mile distances and enjoy panoramic Hudson River views and big eleva..

Take on the Cat's Tail Trail Marathon in the Catskills on Sept 26, 2026, a 26 mile trail with nearly 7,000 feet of climbing and rugged, scenic terrain. Aid stations, race swag and proceeds support land conservation.

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.

Iron Hike Fall Double Kuwohi Trail Marathon Plus Relay is a timed 24 hour trail challenge covering more than 28 miles with epic elevation at Mohawk Mountain in Cornwall Connecticut. Choose solo or relay, run, hike or walk and chase a big da..

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.

Test your trail skills at Big Bear SquaTCh South in Harriman State Park on October 18, 2026, with a rugged 13.1 mile loop or a steep 10K. Expect technical single loop routes with rocky climbs, roots and stunning forest scenery while support..

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.

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.

Join 8 Hours at the Farm at Gurski Farm in Brookfield CT. Run repeated 4 mile loops on rolling single track and farm trails in a community driven, spectator friendly trail running experience.

Join the Fall Back at scenic Jacobsburg State Park with 5 Mile, 3H, or 6H on a roughly 5 mile single track and gravel loop run clockwise. Finishers earn a pin and top athletes receive sustainable medals.

Pocantico Hills Races at Rockwood Hall in Tarrytown on November 7, 2026 feature marathon and half marathon loop courses on wide carriage roads. Expect rolling climbs, Hudson River and Palisades views, fields, forests and car free trails.

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.

Take on the Raven Rocks Run 10k through rocky climbs, ridgelines, ravines and hilly meadows at Ward Pound Ridge Reservation. This scenic but challenging trail route finishes by the old fire tower and closes out the Trail Mix series.

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.

Tarrywile Half Marathon on November 16 2025 challenges runners with technical single track, about 3,000 feet of climbing, and sweeping park views. Choose 10K, half or full marathon in scenic Tarrywile Park.

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.