Trail Running calendar near Norfolk 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, 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.

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.

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 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.

Explore the scenic trails of 100 Acre Woods in Malta, New York. This community event on October 18, 2026 features 2k, 3k, and 5k trail runs. All 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 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.

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.

A weekend Spartan obstacle event at Sunflower Valley Farm featuring sprint, super, kids races and Hurricane Heat formats across muddy woods and creek runs, with team entry options and service-member discounts.

Trail races at Red Wing Recreation Area in Lagrangeville, NY, featuring 100k, 50k and 10k looped courses with notable elevation. The 50k and 100k are UTMB Index races and all finishers receive custom medals.