Trail Running calendar near Billings 2025-2026

Tackle scenic ski area trails at Belleayre Mountain in Climb It For Climate, a community trail race offering challenging 25K and shorter 8K options. Proceeds support The Catskill Center and registration includes a zero carbon travel offset.

Run the Jug End Loop Ultra on August 22, 2026 at Jug End State Reservation in Egremont MA, a six hour timed event on a scenic, hilly 4.2 mile loop through woods and an apple orchard. Rack up laps, earn a handmade mug and support local chari..

Tackle the Shawangunk Ridge Trail near Rosendale NY for sweeping Hudson Valley views across cliffs, sky lakes and rocky ridgelines. Choose 70 Miler, 30 Miler or half marathon for a rugged, self supported navigation challenge.

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..

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.

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.

The 8 Hours At The Farm will take place in Brookfield on Sunday 1 November 2026. You can run 8 hours.

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.

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.