Pawling
Trail Running Calendar near Pawling 2026-2027
Explore the top trail runs near Pawling for 2026-2027! We've gathered 30 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
May 2027
A technical trail race in Beacon NY with a half and full marathon featuring heavy elevation gain, exposed climbs, aid stations, and strict aid station support rules.
A 5k and 1.5 mile walk at Millbrook Vineyards & Winery on May 15, 2027, featuring a mostly grass cross country course and a post run wine pour.
A chip timed 5K at Brooklyn Cider House on May 22, 2027 combining a run or walk with local cider, a shirt, medal, donut and a pour of cider.
A 5 mile trail race at Muscoot Farm on May 23, 2027 with two kids races on farm trails. The event is organized by Run the Farm Races and is sanctioned by USA Track and Field.
June 2027
Multi-day elevation events at Mohawk Mountain offering 12 to 84 hour Solo and team formats, on‑mountain tenting, ski patrol support, and timed lap formats to earn vertical gain.
Trail races at Ward Pound Ridge Reservation on June 6, 2027 include a half marathon and a 10k that pass the summit where the historic fire tower is being reconstructed. Proceeds support Friends of the Fire Tower for accessibility and educational impr..
July 2027
A roughly 5 miles trail run through varied terrain at Bowdoin Park in Wappingers Falls, with a 150 runner cap and awards for overall top finishers.
September 2027
October 2027
Trail endurance events at Mohawk Mountain Ski Area offering solo and FlexRelay team options across 12, 24, 48, 72 and up to 84 hours with distances from 15 to 152.5 miles.