Trail Running calendar near Burlington 2026-2027

An all-trail event on the Moosup Valley State Park Trail in Moosup, CT offering 5K, 8K, 10K and a free Kids Fun Run with post-race shirts or medallions and food at Weidele's; proceeds benefit a local Rotary charity.

A trail running event in Gardiner, NY offering a 5 km run, an optional 10 km two-lap route and a 200 yard kids run, with pre registration T shirt incentives and a sneaker recycling program.

A scored 5K cross country race at Van Cortlandt Park on Sunday, September 27, 2026, featuring varied trail terrain, live runner tracking, awards for top overall finishers, and a free Rising NYRR kids program for ages 2 to 18.

Experience a massive endurance test at Mohawk Mountain Ski Area. This ultra trail event features a 152 mile course with over 72,000 feet of elevation gain to be completed within 84 hours.

A 24 hour trail event at Mohawk Mountain Ski Area in Cornwall Connecticut featuring a Double Kuwohi route of about 28 miles and 13,685 feet of elevation. Participants may run, hike, or walk.

A 30 hour trail ultra at Roosevelt Forest with a 2.23 mile loop, marked course, multiple distance options, and a 100 mile finisher buckle. Aid is centered at the pavilion and one registered pacer is allowed per runner.

Trail races at Bradford Preserve on October 3, 2026 feature 5K, 10K and a free kids run on dirt trails with seasonal course markings and a required orange clothing rule per state regulations.

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 miles trail marathon in Ashford Connecticut on October 4, 2026, run on the Nipmuck Trail with rocky and rooty sections and wood bridges. A two person relay is offered and cutoffs are set by elapsed times.

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.

The Haystack Mountain Challenge on October 4, 2026, features a 5K, 10K and a half marathon across Barbour Woods and Haystack Mountain, with steep climbs, private trail sections, a cupless policy, water stations and on site refreshments.

A 13.7 mile trail race in Cold Spring, NY on October 4, 2026, featuring about 4,000 ft of climbing through the Hudson Highlands during peak foliage. The event 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.

A four day trail event in the Rocky Point pine barrens using a 10.48 mile loop repeated to cover distances from 10 to 150 miles, supported by two stocked aid stations and crew and pacer rules.

A family friendly trail event on October 10, 2026 in Wilton CT offering a 5K and a short accessible run or walk, with participant perks and support for employment initiatives for people with disabilities.

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.

A pickle-themed Halloween obstacle event in Wallkill, NY with an adult 5K and a 1K kids course, themed medals, costumes, mud, and a community-focused Donate a Dragon 3D printing project.

A scenic trail 5K at Blydenburgh County Park in Smithtown, NY on October 11, 2026, with in-person and virtual options, a free kiddie dash, event tee, refreshments, and age group recognition.

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.