Trail Running calendar near Burlington 2026-2027

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.

Join the Charlie Stavros Memorial Beach Run on September 15, 2026 in Westerly, Rhode Island, a free 3 mile beach run honoring a beloved local runner. Enjoy a scenic low tide out and back along Westerly Town Beach with friends and family.

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 the Cat's Tail Trail Marathon in the Catskills, a rugged 26 mile point to point through Slide Mountain Wilderness with nearly 7,000 feet of climbing and stunning mountain views. Aid stations, postrace food and swag, and proceeds supp..

Run the newly restored Moosup Valley State Park Trail in Moosup CT with 5K, 10K and a kids fun run on Sunday September 27, 2026. Postrace medallions or tee shirts, food and drink, leashed dogs welcome, and proceeds benefit the Rotary Club o..

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..

Run for the Pumpkins Trail Run takes place October 3, 2026 in Westerly, Rhode Island, with 10K, 5K and a free 1K kids run at Bradford Preserve. Celebrate fall on scenic preserved trails through Woody Hill and save with fall series bundle di..

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 NipMuck Trail Marathon in Ashford CT on October 4, 2026, a rugged 26.4 miles out and back across rocks, roots, mud and scenic wood bridges. Organized by the Shenipsit Striders, the race supports Connecticut trail stewardship.

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.

A point to point trail race along the Air Line Trail State Park between Willimantic and Putnam, CT. Events include marathon, marathon relay teams, half marathon, 10K and TackleJR, with proceeds supporting local students.

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.

The Grills Trail Run will take place in Misquamicut on Saturday 24 October 2026. You can run between 10 and 10 miles.

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.