Pawling
Trail Running Calendar near Pawling 2026-2027
Explore the top trail runs near Pawling for 2026-2027! We've gathered 29 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
August 2026
A forested 5K on August 9, 2026 at Bridgewater Town Park featuring new trails, modest hills, participation gifts, and prizes for top finishers.
Trail races in Fahnestock State Park near Cold Spring NY offering 50K, 25K and 5.5 mile options with on-course aid and a post-race meal.
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 collected.
September 2026
Timed trail races in Pawling NY offering 24, 12, 6 and 3 hour options on an approximately 1.68 mile loop with on course aid and athlete camping.
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.
October 2026
Experience an ultimate endurance test at Mohawk Mountain by taking on 61 miles and 29,155 feet of elevation gain. Participants have 72 hours to run hike or walk their way to an Everest sized vertical achievement.
A 15-mile trail event at Mohawk Mountain Ski Area in Cornwall, CT with 7,140 feet of elevation and a 12-hour limit; participants may run, hike, walk, or compete in a relay, with registration listed as free for the stated window.
Trail half-marathon in Cold Spring NY on October 4, 2026 featuring 13.7 miles and 4,000 ft of gain through the Hudson Highlands; proceeds support NYNJTC.
Trail running at Mohawk Mountain Ski Area with 5K, 10K, half and marathon routes on ski slopes and state forest, cupless aid stations and finisher medals.
A 3.5 mile trail run and walk on the scenic, flat Mill Pond Trail at Woodtick Recreation in Wolcott CT on October 17, 2026. Tiered online registration is available and a post-event meal is included with registration.
HHNC Meadows & Trails 5K is an off road 5K at Hudson Highlands Nature Center in Cornwall NY on 10/17/2026, featuring meadows, ponds, wooded trails and views of Black Rock Mountain. Entry is $35 and children under 18 run free.
A trail event at Muscoot Farm on October 25, 2026: a five-mile race plus two kids races, kids medals, and Farm Bucks for finishers.
Half marathon and 5K in Garrison NY through Hudson Highlands and past Osborn Castle with proceeds supporting Friends of Philipstown Recreation.
Looped trail races at Red Wing Recreation Area in Lagrangeville, NY offering 100k, 50k, and 10k courses with aid stations and finisher medals.
November 2026
Timed trail event at Gurski Farm in Brookfield CT featuring an 8 hour race, a 4 hour option, and a 5K canicross on a 4 mile loop.
A trail event at Ward Pound Ridge Reservation featuring a 10 km race, a November 100 km virtual challenge, rugged climbs, and fundraising for the Friends of Trailside Museum.
Trail race at Tarrywile Park offering Marathon, Half Marathon and 10K on a loop course with roughly 3K of elevation and technical single-track.