Trail Running calendar near Fairfield 2026-2027

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, plus a two-runner relay option. The course uses a 13 mile segment with out-and-back sections and published cutoffs.

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.

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 multi day trail ultrarunning event near Rocky Point, NY on October 9 to 12, 2026. Runners use a 10.48 mile loop with two aid stations and a range of distances from 10 miles to 150 miles.

A community trail event on 10/10/2026 in Wilton CT featuring a 5K and a 0.75 mile accessible run or walk, event shirts, food and access to farm grounds, and a range of sponsorship options supporting employment 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 four mile off road trail run at Spring Meadow Golf Course in Farmingdale, New Jersey on October 11, 2026. Hand held timing, a free drink ticket and a finisher gift are included; shirts and other merchandise cost extra.

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.

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 technical trail half marathon and steep 10K in Harriman State Park with significant elevation gain. Registration supports the New York and New Jersey Trail Conference and hardship and discount options are available.

A Halloween themed event on Clinton Road in West Milford, NJ offering a 1 mile Zombie Crawl plus 5k and 10k races. The course features zombie volunteers, themed aid stations, and a finish line festival with awards and a costume contest.

An off road 50k around Guilford, Connecticut, on rolling forest roads and rocky single track. The not for profit race supports local land conservation, awards finishers within a 10 hour limit, and offers volunteer opportunities.

Trail and 5K races at Hillside Park on October 18, 2026, benefit a free mammography program. A kids fun run for ages 5 to 12 is included, with chili and vegetarian food and timing by Compuscore.

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 community trail event at Ives Farm featuring a 5K trail race, a youth team relay, and a free kids Pumpkin Dash, plus family activities and proceeds supporting local YMCA and land trust projects.

Experience a unique trail race through the forests and meadows of Muscoot Farm. Enjoy distances for all ages followed by a visit to the local farmers market with your farm buck vouchers.

A 5K Run / Walk and Kids Fun Run at Hallock State Park on October 25, 2026, with a virtual 5K option. Proceeds support the Long Island Greenway and include a post-race wine crawl with vendor specials for participants 21 and over.