Trail Running calendar near Roxbury 2026-2027

Manitou’s Revenge in Windham, NY on June 20, 2026 is a 53 mile ultramarathon across the Catskills with about 15,000 feet of climbing and rugged, technical trails. Expect long self supported stretches and routes that get harsher after dark.

Run the Red Wing Trail Challenge in Lagrangeville, NY on July 5 with 15K, 30K, and 60K options on a runnable 15K loop with varied terrain and serious climbing. Aid stations, lap base for 60K, and post race food make this a true trail day.

Notchview Ultra in Windsor MA, July 10 to 13, 2026 features a scenic 1.9 mile loop with timed options from 6 hours to 100.7 miles. Full aid station, camping and merch plus a lap based charity challenge led by mascot Wally.

Take on rugged ravine trails in Binghamton with 5K, 15K or a timed 12 Hour endurance challenge. Expect steep climbs, creek crossings and technical terrain, plus an option to race with a weighted pack for added grit.

Join the 14th Annual Sweltering Summer Ultra, an 8 hour track challenge at Clapp Park in Pittsfield on August 8, supporting the AYJ Fund for children with cancer. Chip timing, a lively aid station and pizza and ice pops keep energy up.

Test your limits on scenic technical trails in Fahnestock State Park with 50K, 25K and 5.5 mile options on August 15, 2026. Enjoy full aid stations, post race food, swag and proceeds supporting park conservation.

A mountain trail event at Belleayre in the Catskills with a 25K and an 8K open to hikers. The 25K includes about 5000 feet of climbing and the event runs as zero carbon while raising funds for The Catskill Center.

Take on the Jug End Loop Ultra at Jug End State Reservation on August 22, 2026. Run or walk a rolling 4.2 mile loop as many times as you can in six hours through woods, fields, and an apple orchard while supporting local charities.

Run technical trails through old growth forest, waterfalls and steep climbs at the Salt Springs Field, Forest & Falls Trail Races. Choose 5K, 10K or a grueling 50K five loop challenge while supporting park trail conservation.

Run the rugged Shawangunk Ridge Trail near Rosendale NY for epic cliff top views across five states. Pick 70 mile, 30 mile or half marathon courses over rocky, technical terrain in this unsupported, self reliant challenge.

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.

Run scenic truck and horse trails in Charles E. Baker State Forest near Brookfield, NY with 5K, 15K and a rugged 50K option. Fresh grilled food on site and donations support Brookfield Central School seniors.

Join the Connor's Way Scenic Memorial 5 Mile in Hinckley on a wooded five mile course through Adirondack foothills, with in person or virtual options. Proceeds support a memorial and scholarships for students serving underserved areas.

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..

Join the 5th annual Live Well Community Wellness 5K on the scenic Greenway Trail in Dolgeville on September 27, 2026 for a refreshing forest run. Enjoy free refreshments and vendor goodies while supporting local youth with donated sports ge..

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..

Take on Flutters and Foliage Endurance Race in Cohoes NY on Oct 3 2026 with 6 hour, 3 hour and 1 hour solo options plus relays and vendors. Family and dog friendly, proceeds support Flutters of Hope and eating disorder services.

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..

A technical trail half marathon and 10K in Harriman State Park near Tuxedo, NY on October 18, 2026, featuring steep climbs, rocky singletrack, marked routes, aid stations, and a five hour finish cutoff.