Pawling
Walking Events Calendar near Pawling 2026-2027
Monthly updates for Pawling
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Explore the top walking events near Pawling for 2026-2027! We've gathered 37 great walks in the area. Check out our detailed list below to find your next local walk.
October 2026
Walkers can choose 5K, 10K, Half Marathon or Marathon at Mohawk Mountain Ski Area on ski mountain and forest trails, with aid stations and cupless policy.
Walkers can take the 5K route through scenic Cornwall Green and the Cornwall Valley alongside runners and their dogs. Family friendly activities, live music and food accompany the event and proceeds benefit the Little Guild animal rescue.
Walkers can join the 5K in person at Croton Harmon High School, 36 Old Post Road South, then move up to Five Corners to line up for the start. A virtual 5K (3.1 Miles) is available between Oct 10 and 17, and the first 300 5K registrants g..
Untimed 1.7 mi walk starts at Trumbull High School on the A House driveway near the big lot on a mostly flat route. Strollers and leashed dogs are allowed but dogs must start in back and bring a poop bag; walkers should carry their own water.
Walkers take the 4K course from Jimmy Lee Stadium at Crosby High School, on a challenging up, down and flat route around the track and grounds. Parking is in the lots right of the Rotella Magnet School entrance across from the track and packet pick..
Walkers can take the 5K course starting at 5 Van Wyck Lane in Wappingers Falls, NY. A 1K kids fun run runs alongside the running races and proceeds benefit Blood Cancer United.
November 2026
Walkers follow the hilly half marathon route in a timed 4 Miles loop starting at American Legion Post 27 in Litchfield. The walk is timed, uses the same course as the races and includes runner amenities and a finish beer.
Walkers can enter 10K or Half Marathon at Tarrywile Park Danbury on technical single track near 3K elevation with lake views, aid stations and cupless hydration.
The event offers a 5K road loop that starts at Bethel Municipal Center in downtown Bethel and goes through the town neighborhoods. The course is moderately uphill in the first half and downhill in the second half, with the first and last one thir..
December 2026
The 2 Mile walk begins on the Bethlehem Town Green in front of Memorial Hall and follows the 5K course on rolling country roads, turning back at the one mile mark. Parking is at the Bethlehem Fair Grounds with shuttle buses to the Green, and the..
February 2027
Walkers may register to walk the scenic 7.8 miles loop around glacial Lake Waramaug, starting and finishing at Hopkins Vineyard with lake shore views. The course is mainly flat with gentle rolling hills and a final 0.2 miles ascent up Hopkins..
April 2027
The 4k Jay Walk offers a 4 km non competitive route starting at the John Jay Middle School field that follows the wooded John Jay Community Trail. It skips the first out and back loop, starts after the 5k runners enter the woods, and finishes at..
May 2027
The untimed Fun Run/Walk of 3.1 Miles follows the Shepaug River through Steep Rock Preserve with a gradual incline. It starts at 2 Tunnel Road, Washington Depot CT; walkers will not receive a race bib.