Trail Running calendar near Highland Lakes 2026-2027

A forested 5K on the new trails at Bridgewater Town Park in Bridgewater, CT. The 3rd annual event features mixed natural terrain, views of Lake Lillinonah, participant gifts and awards for top finishers.

Step Up for the Brave runs Aug 10–15, 2026 with 90 minute stair climb and walk challenges at Sacred Heart University plus a five day 40,000 step virtual challenge supporting veterans experiencing homelessness.

Trail races in Fahnestock State Park near Cold Spring, NY, offering 50K, 25K and a 5.5-mile course on varied terrain with on-course support, post-race meal, and proceeds supporting land conservation.

A mountain trail event at Belleayre Resort on August 16, 2026 with a demanding 25K and an 8K on ski slopes. The event runs as zero carbon and raises funds for The Catskill Center.

On August 23, 2026 Raptor Ridge stages a 6.5 mile trail race at Westmoreland Sanctuary in Mount Kisco, New York. The event starts and finishes at the Fox Lane High School campus, dogs are not allowed and non perishable food donations are co..

A 50K trail ultra in Forest Park, Queens on August 29, 2026 featuring twelve 2.5 mile loops on the Orange Trail with about 300 feet of climb per loop. Aid stations follow each lap and an eight hour cutoff applies.

Barn B Q Trail Festival on Saturday 9/5/2026 at Masker's Barn pairs a trail run or hike with a five hour barn party featuring BBQ, drinks, music and games. Ticket options cover adults, designated drivers, and children.

Two mile loop trail event at Horseshoe Bend Park near Frenchtown, NJ, offering distance and timed options from 10K to 100 miles. Central Base Camp appears every two miles with food, supplies, camping, and nearby parking.

Sterling Down & Dirty 5K is an annual family friendly obstacle race on Stratford Short Beach each September. Participants tackle more than 18 obstacles, join teams to fundraise for the Sterling Community Center, or volunteer on race day.

A multi-division trail event on the Shawangunk Ridge near Rosendale NY offering 70 mile, 30 mile and half marathon options on an unsupported, fully blazed route with shuttle access and finisher shirts and medals.

Trail event at Hickory Run State Park near Jim Thorpe PA offering 100 km, 50 km and 18 mile options. The 50 km is a figure eight loop with rugged sections including a boulder field and the Shades of Death Trail.

An urban obstacle race on the Jersey City waterfront on September 12, 2026. The event features a fast 3 mile course with 20 plus city-style obstacles, chip timing, new finisher medals, awards, and free race photos.

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.

Run along the Lehigh River on the hard packed D and L Trail. This USATF certified course features a consistent downhill grade and serves as a Boston Marathon qualifier in the Poconos.

Test your endurance at Camp Hart with 4, 6, and 12 hour trail races through technical terrain and scenic hills. Enjoy a supported loop course along the Unami Creek with hot food and diverse trail sections.

Community running event in Lehighton, PA with two 5K course options and a 1 mile walk. Preregistration by September 1 guarantees a T-shirt and swag bag, and chip timing plus an on-site photographer are provided.

A fourth annual 5-mile trail run around Leaser Lake paired with a 100-yard youth Dragonfly Dash, family educational activities, shirts, refreshments, a midway water station, and prizes.

Trail race at Macedonia Brook State Park in Kent, Connecticut on September 13, 2026. Courses of 12K, 25K and 50K on single track forest trails with steep climbs, technical sections and cupless aid stations.

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

Timed trail events at Lakeside Park in Pawling, NY on a 1.68 mile mixed-surface loop offering 3, 6, 12 (day and night) and 24 hour races. The event is cupless, has an aid station and crew area, finisher medals, and buckles for 100+ miles.