Trail Running calendar near Babylon 2026-2027

Run for The Hills is a 4th annual trail 5K on September 12, 2026 at Oswegatchie Hills Nature Preserve, winding around Clark Pond. Expect exposed rocks and roots on scenic trails while helping support preserve maintenance.

FallApple invites runners to scenic trail and road courses through South Mountain Reservation in South Orange on September 12, 2026. Choose distances from 5K to 50 miles and enjoy runnable September trails with aid stations.

Tackle rugged singletrack and sweeping views at Macedonia Trail Race in Kent CT on September 13, 2026, with 12K, 25K and 50K options. Expect steep climbs up Cobble Mountain, fast descents and a festive finish with post race food and medals.

Wild Goose Trail Festival at Wawayanda State Park offers a weekend of trails, films and family fun in mid September 2026. Races range from a kids mile to 100 miles, with camping, panels and fundraising for mental health through Bigger Than..

Charge up the Palisades at the Hook Mountain Ultra in Upper Nyack, NY, with 50 mile and 27 mile trail options featuring big climbs and Hudson River views. Challenging technical terrain and well stocked aid stations keep you moving.

Hit the Hemlock Hills trails in Ridgefield Connecticut on September 20, 2026 for Where the Pavement Ends. Choose a 4.25 mile single loop or an 8 mile double loop over technical, rocky terrain for a true trail challenge.

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..

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.

Take on the Mohawk Mountain Race at Mohawk Mountain Ski Resort with marathon, half marathon, 10K and 5K on challenging ski mountain trails featuring sweeping fall foliage and plenty of climbs and descents. Finishers earn medals and enjoy po..

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 October 17 and 18, 2026, with races from a 1K kids run to the full marathon. Enjoy combined weekend challenges, youth events, and a virtual option to race your way.

Big Bear SquaTCh South is a technical single loop trail race in Harriman State Park on October 18, 2026, with steep climbs, rocky descents and a short scramble. Pick the half marathon or the 10K; spots are capped at 175 and fill fast.

Run Clinton Road with volunteer zombies and themed aid stations for a spooky, fun challenge this October. Choose a Zombie Crawl, 5k or 10k and celebrate at the finish line festival with music, a costume contest and a Survivor Medal for all..

Join FALL Run The Farm on October 25, 2026 at Muscoot Farm in Katonah for a scenic 5 mile trail race plus kids races for ages 2 to 12. Finish with farm market treats and a festive family friendly fall vibe.

Late autumn weekend at Red Wing Recreation Area with looped 100k, 50k and 10k races over rugged, hilly trails. Expect big elevation, full aid, camping for 50k runners and finisher awards, with UTMB Index status for longer distances.

Run a scenic loop of single track and rolling farm trails at Gurski Farm in Brookfield, where the 4 mile course brings you past fellow competitors again and again. Choose 8 hour, 4 hour, 5K or 5K Canicross with medals and food.

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.

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.

Tackle scenic but rugged trails at Tarrywile Park in Danbury with 10K, half and marathon options offering sweeping views of the park and lakes. Expect technical single track, steep climbs, finisher medals and hearty post race snacks.