Trail Running calendar near Roxbury 2025-2026

Join the Sweltering Summer Ultra, an 8 hour track challenge at Clapp Park in Pittsfield where runners and walkers lap a cinder loop and hit a marathon split. Chip timing, live leaderboard, refreshments and awards support the AYJ Fund.

Climb It For Climate invites trail runners to tackle scenic routes at Belleayre Mountain in Highmount, NY on August 16, 2026, with 25K and 8K options and a hike option for the longer course. Registration offsets travel carbon and supports T..

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..

Explore rugged single track through old growth forest at the Salt Springs Trail Races on August 29, 2026 in Montrose PA. Choose 5K, 10K or a demanding 50K five loop course with steep climbs and technical descents while supporting the park.

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.

Tackle technical single track and big climbs at the Macedonia Trail Race in Kent, Connecticut. Choose 12K, 25K, or 50K loops with Cobble Mountain views and rugged trails for a rewarding, scenic challenge.

Run scenic truck and horse trails through the Charles E Baker State Forest with options for 50K, 15K or 5K. Enjoy fresh grilled food, friendly vibes and the chance to chase course record prizes in the 50K and 15K.

The Cat's Tail Marathon will take place in Shandaken on Saturday 26 September 2026. You can run 26 miles.

Join the Live Well Community Wellness 5K on Sunday, Sept 27, 2026 for a scenic forest run along the Greenway Trail in Dolgeville, NY. Proceeds provide free sports equipment to local youth and early registrants receive a free race tee.

Experience the Iron Hike Fall Series, a four day trail festival in Cornwall, CT from October 1 to 4, 2026, featuring epic ultra distances and relays. Run, hike, or walk timed courses that test endurance and celebrate grit.

Take on a 24 hour trail challenge at Mohawk Mountain with a 28 plus mile course and huge elevation gain that rewards grit and strategy. Run, hike, or walk solo or as a relay with veteran owned IronHike Endurance Productions.

Conquer Mohawk Mountain on scenic but rugged trail courses with 5K, 10K, half marathon and marathon options, big climbs and singletrack. Runners earn finisher medals, enjoy aid stations and follow a cupless policy to reduce waste.

Tackle rugged trails at Big Bear SquaTCh South, a half marathon and 10K in Harriman State Park with steep climbs, roots and a short scramble. Small field and proceeds benefit trail maintenance for an intimate, rewarding race.