Trail Running calendar near Cheshire 2026-2027

A 5K fall trail run and walk at Ryan Park in North Kingstown on October 3, 2026, benefiting the North Kingstown Firefighters Association. Registrations before September 14 include a race day t shirt and top finishers receive medals.

Run through 300 acres of scenic vineyards on a flat trail course in Peconic. Enjoy live music, food trucks, and a post-race glass of wine at this chip-timed autumn event.

A 26.4 mile trail marathon on Connecticut’s Nipmuck Trail featuring rocks, roots, mud and wood bridges, with an optional two-person relay and elapsed time cutoffs. Organized by the Shenipsit Striders in Ashford, CT.

A four mile trail race through Irvington Woods on October 4, 2026, with varied terrain including climbs and stairs; start and finish at Irvington High School. Registration runs March 15 to September 4 with a $40 fee.

A fall trail race day in Norfolk, CT offering 5K, 10K and a half marathon with steep climbs, private-trail sections, a cupless policy with water stations, and on-site food and beverage vendors.

A 13.7 mile trail race in Cold Spring, NY on October 4, 2026 with about 4,000 ft of elevation gain through the Hudson Highlands during peak foliage. It is an UTMB Index Race and supports the NYNJTC.

NYRR Cross Country Series #2 is a scored 5K cross country race at Van Cortlandt Park in the Bronx on October 4, 2026. The event includes a free Rising NYRR kids program and a member standby registration option.

Runners climb the Empire State Building's 86 flights and 1,576 stairs to the observatory in this New York tower race on 10/06/2026. Multiple entry categories are offered with different registration windows and fees.

A four day trail event on Long Island using a 10.48 mile loop repeated to reach distances from 10 to 150 miles, with two stocked aid stations, crew access and specified pacer rules.

A community trail event in Wilton, CT on Oct 10, 2026, supporting the Prospectors' mission. Features a 3.1 mile trail race, an accessible stroller run, on-site food, entertainment, and access to farm grounds.

Experience a trail race at Mohawk Mountain Ski Resort featuring distances from 5k to a full marathon. Run through fall foliage on a course that includes steep ski slopes and the scenic Mohawk State Forest.

A single-loop trail half marathon through five parks in lower Westchester County, New Rochelle. Most of the course is on dirt and wooded trails and passes through areas with visible wildlife.

The Obstacle Wonderland Hallo-Weird Adult 5k Obstacle Course Race will take place in Wallkill on Sunday 11 October 2026. You can run 5 kilometers.

Experience Long Islands scenic Robert Moses Causeway in this multi day running event. Support local veterans while choosing between marathon, half marathon, 10k, and 5k distances with finisher medals for all participants.

Experience a point to point trail race in Northeast Connecticut on the Airline Trail. Choose between marathon, half marathon, and 10K distances with individual or relay team options to support local student education.

A 3.5 mile trail run and walk on the scenic, flat Mill Pond Trail at Woodtick Recreation in Wolcott CT on October 17, 2026. Tiered online registration is available and a post-event meal is included with registration.

A fall trail event in Harriman State Park offering a technical **13.1M** and **10K** with steep climbs, rocky singletrack, aid stations, and adaptive support; the field is capped and proceeds support local trail maintenance.

Bimblers Bluff 50K on October 18, 2026 in Guilford, CT is an off road ultramarathon over rolling forest roads and rocky single track through interconnected woodland preserves. The course does not require multiple loops and includes aid stat..

A fall trail event at Grills Preserve in Westerly with 10 mile and 10 km courses across single-track trails and riverfront sections. Club timing is used, orange clothing is required, and post-race refreshments are provided.

A fall trail race at Mt. Tom State Park on October 24, 2026, with single and relay options from 5k to 25k on rugged single-track terrain. The event supports Kestrel Land Trust and includes aid stations, medical crews, and awards.