Trail Running calendar near Waterbury 2026-2027

Experience the rugged beauty of northwest Connecticut at Macedonia Brook State Park. Featuring single track trails and views of the Catskill Mountains, this event offers 12K, 25K, and 50K distances for trail runners.

The Corporate Fun Run Pier 84 Manhattan will take place in New York on Monday 14 September 2026. You can run 5 kilometers.

A free 3 mile out-and-back beach run at Westerly Town Beach held at low tide. The community event is organized by the Westerly Track Club and the Stavros family as a memorial run.

A multi-race trail festival at Lakeside Park in Pawling, NY offering timed 24, 12 day, 12 night, 6 and 3 hour events on an about 1.68 mile loop with on-course aid, music, and finisher medals.

A weekend trail festival at Wawayanda State Park offering races from a 1 mile kids run to a supported 100 mile event with a 36 hour cutoff, camping, panels, aid stations and nonprofit partnerships for community support.

A USATF sanctioned trail ultra near Upper Nyack, NY offering a 50 mile race with about 9,700 feet of gain and a 27 mile mountain marathon. The course uses a 4 mile out and back plus repeated 11.5 mile loops along the Palisades ridge and Hud..

A community fundraiser in Pomfret Center with a trail 5K and a 0.5 mile kids run supporting the Pomfret Community School PTO. Early and later registration fees differ and awards plus finisher medals are given.

Trail races in Ridgefield CT offering a single loop of about 4.25 miles or a double loop of about 8 miles through Hemlock Hills and Pine Mountain. The technical, rocky course starts and ends at the Lake Windwing ballfields.

A 5K trail run at Winding Trails in Farmington on the designated course around Walton Pond, with registration from February 20 to September 20 and a $35 fee; overall and age-group awards plus a prize for the first local finishers.

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 26 miles trail race in the Slide Mountain Wilderness near Shandaken, NY, featuring nearly 7,000 feet of vertical gain and technical, rocky terrain. Proceeds support Run Wild, Inc and several race services are provided.

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.

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 loop ultra at Roosevelt Forest in Stratford CT on a 2.23 mile course with roots, rocks and a notable hill. Field limited to 50 runners; completing 45 loops within 30 hours earns a finisher buckle.

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 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.