Trail Running Calendar Connecticut 2025-2026

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.

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.

Hit the newly restored Moosup Valley State Park Trail on Sunday, September 27 for scenic 5K, 10K and a kids fun run on all trail terrain. Post race food and gear, leashed dogs welcome, and proceeds support the Rotary Club of Plainfield.

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.

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.

Tackle the rugged NipMuck Trail Marathon in Ashford CT, a 26.4 mile trail test through rocks, roots, mud and wooden bridges. Run solo or as a two person relay and expect a challenging, hilly second half that rewards grit.

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 a scenic 13.1 mile trail half in Roosevelt Forest, eight laps of a 1.64 mile wooded loop with roots, rocks and rolling hills. Costumes are encouraged with prizes, plus a book drive to benefit local kids.

Join a scenic 3.5 mile Thanksgiving trail run or walk around Scoville Reservoir in Wolcott CT on November 26, 2026 to benefit the Endometriosis Foundation of America. Enjoy post race yoga, finisher medals, swag and a dog friendly vibe.