Trail Running calendar near Cheshire 2026-2027

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.

Charity 5K run and 1.5 mile walk in Huntington MA on a mixed pavement, field and trail course that finishes at Littleville Dam.

An obstacle based 5K at Short Beach Stratford with 18 plus obstacles, family friendly rules, and proceeds benefiting the Sterling Community Center.

A trail event in Rosendale, NY featuring 70 mile, 30 mile and half marathon divisions along the Shawangunk Ridge. The course covers varied terrain, is unsupported, and uses shuttle transport and checkpoint controls.

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.

Pittsfield State Forest trail races on September 12, 2026 offering 50k, 25k, 15k and a new 5 mile option on a double-loop course with three aid stations.

Trail race in Macedonia Brook State Park, Kent CT offering 12K, 25K and 50K loop courses with significant elevation, aid stations, and a cupless policy.

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 trail event at Nyack Beach State Park offering a 50 mile ultra with about 9,700 feet of ascent and a 27 mile mountain marathon with about 4,900 feet, on looped singletrack with river views.

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.

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.

A women only 5K obstacle mud run at Carter & Stevens Farm in Barre, MA on September 20, 2026. The course has 18+ obstacles, welcomes participants ages seven and up, and emphasizes teamwork over competition.

A 5K trail race at Goddard Park in Warwick, RI on September 26, 2026, over fields and wooded trails along Greenwich Bay with onsite parking and age-group awards.

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.

A trail event on the Moosup Valley State Park Trail featuring 5K, 8K, 10K and a Kids Fun Run. Parking and the finish are at Weidele's Pizza with post-race food, awards and a medallion or shirt option.