Trail Running calendar near Waterbury 2026-2027

A *3.5 mile* trail run/walk at Woodtick Recreation Area in Wolcott, CT on May 17, 2026. Proceeds support the Wolcott Cross Country Teams and participants receive a free entry to the CT Food Truck Battles Festival.

Run or walk the Never Stop Running Foundation Long Island Lemonade Trail 5K on May 23, 2026 at Blydenburgh County Park, with an in person or virtual option. Free Kiddie Dash and proceeds benefit the foundation.

Join the Mine Hill Half Marathon on May 24, 2026, starting and finishing at Mine Hill Distillery in Roxbury, CT. Tackle a scenic hilly road course and celebrate afterward with food, live music and distillery samples.

Join the Forest Park Runners Classic, a scenic 4 mile road and trail out and back in Forest Park, Queens, on Sunday May 24, 2026, featuring chip timing and an overhead finish clock. Pre register for a tech shirt and enjoy post race snacks a..

A multi day endurance series at Mohawk Mountain in Connecticut offering solo and team trail events from 15 to 152+ miles with timed formats up to 84 hours. Tenting, support stations, and personalized bibs and medals are provided.

A scenic 10 km run starting and finishing at historic Rockwood Hall in Rockefeller State Park Preserve. The event includes a separate kids race for ages 12 and under and directs proceeds to carriage road maintenance.

A community 5K trail run, walk and hike in Eisenhower Park Milford on June 7, 2026 supporting the Milford Rotary and the Beth El Center. The course uses a high school cross country route with mostly flat sections and some rolling hills.

The Norbrook Farm Brewery Trail Festival will take place in Colebrook on Saturday 13 June 2026. You can run between 5 and 4 hours.

Trail action at Mansfield Hollow State Park with a scenic yet challenging 15 Miler along the Nipmuck Trail and a new technical 5K inside the park. Expect river views, woods, bridges and climbs while supporting Connecticut trail stewardship..

Manitou’s Revenge in Windham, NY on June 20, 2026 is a 53 mile ultramarathon across the Catskills with about 15,000 feet of climbing and rugged, technical trails. Expect long self supported stretches and routes that get harsher after dark.

Early morning trail run in Gay City State Park offering 3, 5 and 8 mile races. The 8 mile is part of the Blue Blazed and USATF CT MUT series and includes teams of three competing for prize money.

Run the Red Wing Trail Challenge in Lagrangeville, NY on July 5 with 15K, 30K, and 60K options on a runnable 15K loop with varied terrain and serious climbing. Aid stations, lap base for 60K, and post race food make this a true trail day.

Notchview Ultra in Windsor MA, July 10 to 13, 2026 features a scenic 1.9 mile loop with timed options from 6 hours to 100.7 miles. Full aid station, camping and merch plus a lap based charity challenge led by mascot Wally.

Pinky's Rock n Rolla is a lively 4 mile trail race through Forest Park's scenic trails celebrating Pinky the Pacer. Finishers get medals, top three men and women earn prizes, dogs welcome, and proceeds benefit Puppy Kitty NYCity.

A 5.5 mile trail race at Soapstone Mountain featuring six ascents and about 1500 feet of climbing. The route circles the mountain with multiple steep rocky sections, limited aid access, and a field limited to 50 runners due to parking.

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.

Interstate 17 is a challenging 17 mile trail run on August 8, 2026 in Closter NJ that traces Hudson River viewpoints. Expect rugged technical singletrack, steep climbs and boulder scrambles across four loops with fully stocked aid stations.

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.