Trail Running calendar near Norfolk 2026-2027

A trail event in Rosendale, NY on the Shawangunk Ridge Trail offering 70 mile, 30 mile, and half marathon divisions. The course crosses varied terrain and is minimally supported so participants must carry food and water purification.

Trail race at Macedonia Brook State Park on 13 September 2026 featuring single-track forest trails, climbs, viewpoints and three distances: 50K, 25K and 12K.

Timed trail races at Lakeside Park in Pawling, NY on an approximately 1.68 mile loop with 3, 6, 12 and 24 hour options, cupless format, aid station supplies, finisher medals and specific support and pacer rules.

The Hook Mountain Ultra is a demanding 50-mile or 27-mile trail race in Upper Nyack, NY. The course features repeated loops with significant climbs, ridge running, and scenic Hudson River views. It includes full aid station support and has..

The Where the Pavement Ends trail race offers a technical 4.25-mile single loop or an 8-mile double loop through the Hemlock Hills. It's part of the multi-race Trail Mix Series. Both races start and finish at the Lake Windwing ballfields in..

Run a scenic 5K trail race through 300 acres of natural terrain at Winding Trails in Farmington. Compete for age group awards and the local Lee Chisholm Award on a course surrounding Walton Pond.

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 point to point trail marathon in the Catskill Mountains with almost 7,000 feet of elevation gain, multiple aid stations, finishline food and proceeds that support land conservation. Registration opens May 1, 2026.

Run the Moosup Valley All Trail Race on September 27, 2026. Choose from a 5K, 8K, or 10K on the 100% trail course at Moosup Valley State Park. After the run, enjoy post-race food and a choice of a shirt or medallion.

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.

Experience an ultimate endurance test at Mohawk Mountain by taking on 61 miles and 29,155 feet of elevation gain. Participants have 72 hours to run hike or walk their way to an Everest sized vertical achievement.

This 24-hour trail challenge in Cornwall, CT, covers over 28 miles and 13,685 feet of elevation gain. Participants can run, hike, or walk the double marathon distance or tackle it as a relay.

A 30 hour looped trail ultra at Roosevelt Forest in Stratford, CT, run on a 2.23 mile lap with roots, rocks and a notable hill. Multiple distances are offered and awards are based on most miles completed during the time limit.

A fall endurance event in Cohoes, NY offering 6 hour solo and relay, 3 hour and 1 hour timed formats, with buckles for solo runners over 26.2 miles, swag and finisher awards, and fundraising for Flutters of Hope Inc.

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.

Experience an old school trail race along the historic Nipmuck Trail in Connecticut. This 26.4 mile double out and back event follows the blue blazed trails through challenging New England terrain.

A 4 mile trail race through the Irvington Woods on October 4, 2026, with varied terrain and stairs. Start and finish are at the back soccer field of Irvington High/Middle School; registration runs March 15 to September 4 with a $40 fee.

Trail races and a half marathon take place around Barbour Woods and Haystack Mountain in Norfolk, CT on October 4, 2026. Routes include single track and carriage roads and the half marathon features over 2000 feet of elevation gain.

A multi-day trail event near Rocky Point, NY, run on a 10.48-mile loop with distance options from 10 miles to 150 miles. Two staffed aid stations provide food and volunteer support; pacers and crews are allowed with prior notice.

Third annual trail event on October 10, 2026 in Wilton, CT featuring a 5K and a 1 mile accessible run/walk, with food and entertainment, supporting employment opportunities for people with disabilities.