Trail Running calendar near Cheshire 2026-2027

A community potluck and trail run in Tolland, CT on August 15, 2026. Participants run 5K loops during an eight hour period, earn raffle tickets per loop, and receive a 50th anniversary gift after completing a loop.

Trail races in Fahnestock State Park near Cold Spring, NY on August 15, 2026, offering 50K, 25K and a 5.5-mile option across mixed dirt roads and single track. On-course aid and post-race meal included; proceeds support park conservation.

A timed 5K at Brimfield Winery on August 15, 2026, run on a mostly grass cross country style course. Registration options include a standard 5K with a postrace wine pour and a volunteer plus run option.

A timed six hour ultramarathon on a 4.2 mile loop at Jug End State Reservation in Egremont, MA. The wooded course includes fields and an apple orchard and benefits the Louison House.

A 5K cross-country race at Waters Farm in Sutton, MA, marking the fourth running of the Old Goat Track Club XC Classic with on-site parking, finish-line water and fruit, portable toilets, and awards for individual and team results.

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 multi event ultramarathon in West Greenwich, Rhode Island featuring a repeated 10 mile loop with desert, pavement and trail sections. Chip timed events include aid stations, a finisher sweatshirt and a buckle for 100 mile finishers.

A 50K in Forest Park Queens run as 12 laps of a 2.5 mile Orange Trail loop, each lap adding about 300 feet of climb and with aid stations after every circuit. The event combines a grassroots race atmosphere with an 8 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.

A family friendly beach 5k obstacle race in Stratford each September, featuring 18 plus obstacles and community fundraising for Sterling Community Center programs. Participants and teams raise funds while running, walking, or navigating obs..

A trail event on the Shawangunk Ridge near Rosendale offering 70 mile, 30 mile, and half marathon divisions over rugged, minimally supported terrain with shuttle logistics and enforced checkpoints.

A group run along the Farmington Canal Heritage Trail covering roughly 56 miles from West Suffield to New Haven, held as a fundraiser for Mental Health Connecticut. The event is largely self supported with basic volunteer aid stations and a..

A trail race day at Pittsfield State Forest with 50k, 25k, 15k and a new 5 mile option, a double-loop course with three aid stations and charity fundraising through BURCS and Free to Run.

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 multi-race trail festival at Lakeside Park in Pawling, NY offering timed 24, 12 day, 12 night, 6 and 3 hour events on an about 1.68 mile loop with on-course aid, music, and finisher medals.

A USATF sanctioned trail ultra near Upper Nyack, NY offering a 50 mile race with about 9,700 feet of gain and a 27 mile mountain marathon. The course uses a 4 mile out and back plus repeated 11.5 mile loops along the Palisades ridge and Hud..

A community fundraiser in Pomfret Center with a trail 5K and a 0.5 mile kids run supporting the Pomfret Community School PTO. Early and later registration fees differ and awards plus finisher medals are given.

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.