Trail Running calendar near Waterbury 2026-2027

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 six hour loop ultra at Jug End State Reservation in Egremont, MA on August 22, 2026. Runners complete as many 4.2 mile laps as they wish; a 0.75 mile mini loop is available in the final hour for distance milestones.

Run the Old Goat Track Club XC Classic at Waters Farm in Sutton, a spike friendly 5K cross country loop and USATF New England Grand Prix stop. Perfect for teams and individual racers, with finish line snacks and a nearby after party.

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.

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 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.

Join the Charlie Stavros Memorial Beach Run on September 15, 2026 in Westerly, Rhode Island, a free 3 mile beach run honoring a beloved local runner. Enjoy a scenic low tide out and back along Westerly Town Beach with friends and family.

Wild Goose Trail Festival at Wawayanda State Park offers a weekend of trails, films and family fun in mid September 2026. Races range from a kids mile to 100 miles, with camping, panels and fundraising for mental health through Bigger Than..

Charge up the Palisades at the Hook Mountain Ultra in Upper Nyack, NY, with 50 mile and 27 mile trail options featuring big climbs and Hudson River views. Challenging technical terrain and well stocked aid stations keep you moving.

Hit the Hemlock Hills trails in Ridgefield Connecticut on September 20, 2026 for Where the Pavement Ends. Choose a 4.25 mile single loop or an 8 mile double loop over technical, rocky terrain for a true trail challenge.

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..

Run the newly restored Moosup Valley State Park Trail in Moosup CT with 5K, 10K and a kids fun run on Sunday September 27, 2026. Postrace medallions or tee shirts, food and drink, leashed dogs welcome, and proceeds benefit the Rotary Club o..

A multi-day ultratrail series at Mohawk Mountain Ski Area in Cornwall CT from October 1 to October 4, 2026 featuring events of roughly 152, 100 and 61 miles with large cumulative elevation gains and individual and relay formats.

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..

Run for the Pumpkins Trail Run takes place October 3, 2026 in Westerly, Rhode Island, with 10K, 5K and a free 1K kids run at Bradford Preserve. Celebrate fall on scenic preserved trails through Woody Hill and save with fall series bundle di..

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.

Take on the NipMuck Trail Marathon in Ashford CT on October 4, 2026, a rugged 26.4 miles out and back across rocks, roots, mud and scenic wood bridges. Organized by the Shenipsit Striders, the race supports Connecticut trail stewardship.

A series of trail races in Rocky Point NY using a 10.48 mile loop repeated for distances from 10 mile to 150 mile. Two aid stations provide Hylē Hydration and food, and some distances include night race options.

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 single-loop half marathon through five parks in lower Westchester County, New York, starting at the Thomas Paine Cottage and finishing at New Rochelle High School. Mostly shaded dirt trails with varied wildlife and published race results.