Trail Running calendar near Avon 2026-2027

Ridge Reaper Trail Runs returns Aug 1, 2026 at Ward Pound Ridge Reservation near NYC, offering multiple distances from runnable loops to epic 50 mile challenges. Expect wooded technical trails, ridge views, finisher medals and podium awards..

Run the Stonington Cross Country 5K in Pawcatuck at Stonington High School on Wednesday August 5. The scenic course starts and finishes on the track and winds through quiet streets, trails and grassy crossings for a community run.

Join the 14th Annual Sweltering Summer Ultra, an 8 hour track challenge at Clapp Park in Pittsfield on August 8, supporting the AYJ Fund for children with cancer. Chip timing, a lively aid station and pizza and ice pops keep energy up.

Run loops on a roughly 5K trail course during an eight hour celebration with the Shenipsit Striders in Tolland. Bring food, enjoy the grill, earn raffle tickets and a 50th anniversary gift while supporting local trail stewardship.

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.

Take on the Jug End Loop Ultra at Jug End State Reservation on August 22, 2026. Run or walk a rolling 4.2 mile loop as many times as you can in six hours through woods, fields, and an apple orchard while supporting local charities.

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.

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.

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..

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..

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.

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..

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..