Trail Running calendar near Bridgewater 2026-2027

Experience a technical seventeen mile trail run along the Hudson River cliffs with over five thousand feet of elevation change. High endurance is required for this rugged course featuring boulder scrambles and scenic river views.

The Running Wild at Wildwood Trail 2.5 Mile Trail Run/Walk will take place in Wading River on Saturday 8 August 2026. You can run 3 miles.

Experience the technical singletrack trails of Stokes State Forest at this inclusive trail party featuring 5K, 10K, and 17 mile options for runners and hikers of all paces.

A forested 5K on the new trail network at Bridgewater Town Park in Bridgewater, CT on August 9, 2026. The course uses packed dirt and natural paths with gentle hills and views of Lake Lillinonah; participants receive a race-day gift.

A loop-based trail event at Crandall's Park on August 15, 2026 featuring roughly 5K loops, potluck food, raffles with tickets earned per loop, hidden treasures on course, and a 50th anniversary gift for anyone who runs a loop.

Trail races at Fahnestock State Park in Cold Spring NY on August 15, 2026 offer three distances across varied terrain with aid stations, a post race meal, and proceeds supporting land conservation.

Experience the beauty of the Catskill Mountains at this zero carbon event featuring a 25K trail run and an 8K ski slope course. Both distances are open to runners and hikers looking for significant elevation gain and mountain views.

A six hour lap ultra on a 4.2 mile wooded and orchard course at Jug End State Reservation on August 22, 2026, featuring 830 feet of elevation change per lap and a 0.75 mile mini loop in the final hour; proceeds benefit Louison House.

A 6.5 mile trail race at Westmoreland Sanctuary in Mount Kisco on August 23, 2026, with start and finish at the Fox Lane High School campus and a non-perishable food collection for the Mt. Kisco Food Pantry.

Experience Stratford’s dirty day on the beach at this 5k obstacle race featuring 18+ challenges through sand and water to support the Sterling Community Center.

Experience a scenic 3.3 mile trail run or hike through the Oswegatchie Hills Nature Preserve. Support local land conservation while enjoying a timed course around Clark Pond followed by an awards ceremony with refreshments.

A trail event near Rosendale New York with 70 mile, 30 mile, and half marathon options along the Shawangunk Ridge. The course is rugged and minimally supported so participants must carry food and water purification.

The City Challenge Race returns for its 12th year on the Jersey City waterfront. This is the only event of 2026, featuring a fast 3-mile urban obstacle course with over 20 unique challenges. Participants receive finisher medals, professiona..

Experience a diverse trail race at South Mountain Reservation featuring fire roads and single track trails. Choose from multiple distances ranging from a 5K to 50 miles with aid stations every three miles.

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.

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

A mid-September trail festival at Wawayanda State Park offering races from a 1 mile kids run to 100 mile and 36 hour options, varied trail terrain, free weekend camping, on-course support, and a partnership with Bigger Than The Trail.

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.