Trail Running calendar near Rocky Point 2026-2027

A community eight hour loop run at Crandall's Pavilion in Tolland, CT, organized by the Shenipsit Striders. The free event features repeated roughly 5K trail loops, potluck food, and an optional donation jar.

Trail races in Fahnestock State Park near Cold Spring, NY on August 15, 2026, offering 50K, 25K, and 5.5‑mile options with aid stations, a post-race meal, and proceeds supporting park conservation.

Experience a community trail run through Elm Ridge Park benefiting the Rocky Hill Fire Department and Library. This event features a two loop trail course for adults and a fun medal race for kids.

On August 23, 2026 Raptor Ridge stages a 6.5 mile trail race at Westmoreland Sanctuary in Mount Kisco, New York. The event starts and finishes at the Fox Lane High School campus, dogs are not allowed and non perishable food donations are co..

A 50K trail ultramarathon in Forest Park, Queens. The race is 12 laps of a 2.5 mile counterclockwise loop with about 300 ft climb per lap, aid stations after each lap, and an eight hour cutoff.

Experience a scenic 3.3 mile trail run or hike through the Oswegatchie Hills Nature Preserve. Support local land conservation while enjoying a timed course around Clark Pond followed by an awards ceremony with refreshments.

An obstacle based 5K at Short Beach in Stratford CT featuring more than 18 obstacles and a family friendly course. Proceeds support the Sterling Community Center including the food pantry and youth programs.

City Challenge Race returns to Jersey City on September 12, 2026 with a fast 3-mile urban obstacle course featuring 20+ city-style obstacles, new finisher medals, professional chip timing, awards and free race photos.

Experience a diverse trail race at South Mountain Reservation featuring fire roads and single track trails. Choose from multiple distances ranging from a 5K to 50 miles with aid stations every three miles.

A group run along the Farmington Canal Heritage Trail covering about 56 miles from West Suffield to New Haven. It is a fundraiser for Mental Health Connecticut and requires self support with a 14 hour time limit.

Experience the rugged beauty of northwest Connecticut at Macedonia Brook State Park. Featuring single track trails and views of the Catskill Mountains, this event offers 12K, 25K, and 50K distances for trail runners.

The Corporate Fun Run Pier 84 Manhattan will take place in New York on Monday 14 September 2026. You can run 5 kilometers.

A free 3 mile out-and-back beach run at Westerly Town Beach held at low tide. The community event is organized by the Westerly Track Club and the Stavros family as a memorial run.

A timed trail festival at Lakeside Park in Pawling offering 24, 12, 6 and 3 hour events on an approximately 1.68 mile mixed surface loop with aid station items, a cupless policy, and finisher medals.

A weekend trail festival in Ringwood State Park featuring a 100 mile race with a 36 hour cutoff, multiple shorter distances, Friday panels and film screening, free camping, and nonprofit partnerships supporting mental health.

A loop-based trail event in Upper Nyack with 50 mile and 27 mile options, significant elevation, three aid stations, and a 14 hour cutoff. Parking and nearby overnight accommodations are coordinated with a local retreat center.

Trail races in Ridgefield CT offering a single loop of about 4.25 miles or a double loop of about 8 miles through Hemlock Hills and Pine Mountain. The technical, rocky course starts and ends at the Lake Windwing ballfields.

A 5K trail run at Winding Trails in Farmington on the designated course around Walton Pond, with registration from February 20 to September 20 and a $35 fee; overall and age-group awards plus a prize for the first local finishers.

Experience the technical terrain of Cockaponsett State Forest with 4 and 9 mile trail races. Navigate hills and rocky paths in Chester to support PanCAN and the Blue Blazed Trail Race series.

Trail races in Burlington CT organized by the Burlington Land Trust as a fundraiser. Courses on the Tunxis Trail cover mixed terrain and visit landmarks such as the CT State Trout Hatchery, Nassahegan State Forest, and Devil’s Kitchen.