Trail Running calendar near Poughkeepsie 2026-2027

Run through the historic carriage roads of the Rockefeller State Preserve in the Hudson Valley. The single-loop marathon and half marathon courses pass fields, stone walls, and scenic vistas without any pavement or cars. It's a walk-friendl..

A trail 10k at Ward Pound Ridge Reservation paired with a November virtual 100k challenge that rewards finishers with a custom engraved woodallion; the race uses rocky ridgeline trails and includes an on-course water stop near the fire towe..

The NYC Trail Mix will take place in Richmond County on Saturday 14 November 2026. You can run 50 kilometers.

The SOMO Winter Trail Series will take place in South Orange on Saturday 14 November 2026. You can run between 5 and 13 miles.

A technical trail event at Tarrywile Park in Danbury offering 10K, half marathon and marathon distances with significant elevation gain; finisher medals, podium awards, and post-race food are provided.

A trail half marathon in Roosevelt Forest on November 21, 2026, run as eight 1.64 mile loops over singletrack and doubletrack with roots, rocks, and rolling hills. Costumes are encouraged and a book drive supports Books4Everyone.

The FEAR Trail Fest is a 5-mile trail race on the scenic Yellow Trail in New Jersey's Lewis Morris Park. With a runnable mix of rocks, roots, and climbs, it welcomes everyone from first-timers to veterans. The event focuses on sustainabilit..

A Thanksgiving morning trail run supporting endometriosis research. Choose a run or walk on the 3.5-mile Mill Pond Trail, followed by complimentary yoga. All participants get a finisher medal and swag bag.

Trail loops at South Mountain Reservation with 5K laps used for 5K, 10K, 25K, 50K and a kids mile. Family friendly, volunteer supported, and partnered with Bigger Than The Trail; the event typically sells out.

Rob's Trail Run Edition stages 5K trail runs for adults and for high school or youth runners at Stillwell Woods Preserve in Woodbury, NY. The event supports The Center for Developmental Disabilities and is produced by RaceAwesome.

The Tower Tag Challenge is a timed trail run in Connecticut's Sleeping Giant State Park. Runners complete 3.4-mile laps up and down the scenic Tower Trail within an 8-hour or 4-hour window. The event features awards, post-race refreshments,..

A 5K trail race at Roosevelt Forest in Stratford, CT on December 19, 2026, run over two 1.55 mile loops. Holiday costumes are welcome, awards are given to top finishers, and all finishers receive a custom medallion; proceeds support local c..