Trail Running calendar near Great Barrington 2025-2026

The Shenipsit Striders Fatass will take place in Tolland on Saturday 15 August 2026. You can run 5 kilometers.

Climb It For Climate at Belleayre Mountain on August 16, 2026 offers 25K and 8K mountain courses or an early start hike. Join community events, enjoy plant based aid, and support The Catskill Center with an eco conscious approach.

The Jug End Loop Ultra will take place in Great Barrington on Saturday 22 August 2026. You can run 4 miles.

Run the Shawangunk Ridge Trail in Rosendale NY on Sep 12, 2026. Choose 70 mile, 30 mile or half marathon routes through rocky ridgelines, waterfalls and cliffs in a self supported backcountry 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.

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

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.

Enjoy a scenic 5 mile trail run through historic Muscoot Farm in Katonah, with fun kids races and farm market perks. Finishers get Farm Bucks to spend at the market, making this a perfect fall family run and local food celebration.

Run 13.1 miles on forest trails at the Storybook Half Marathon in Roosevelt Forest, Stratford CT, completing eight scenic loops of single and doubletrack. Wear a costume, enjoy post race perks, and donate children's books to Books4Everyone.