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Walking Events Calendar near Kingston 2026-2027

Monthly updates for Kingston

Get new running races (and updates) in your inbox every month.

Explore the top walking events near Kingston for 2026-2027! We've gathered 8 great walks in the area. Check out our detailed list below to find your next local walk.

August 2026
Walkers can choose a 1.5 Miles route or tackle the 5K course starting and finishing at Millbrook Vineyards & Winery, across mostly grass cross country terrain with some mildly challenging sections. Registration includes a post walk pour of wi..
September 2026
Walkers take a scenic 5K on the Ashokan Reservoir Promenade, mostly flat with one uphill at the start and much of the route closed to traffic. Parking is at Brown's Station the Aerators; a water stop is provided and kids under 10 are free though..
Walkers can join the family friendly 5K Run/Walk held entirely on the O&W Rail Trail behind 51 Hurley Avenue. The route stays on the rail trail, providing a trail setting for walkers alongside the run.
Walkers can choose the 5K route beginning at Memorial Park, 2 Robert Cahill Dr in Beacon. The course is relatively flat but includes a hill near the start, and a virtual 5K option is available.
October 2026
Walkers are welcome on the 5K course that starts and finishes at the Morning Star building, 79 to 83 East Chester Street, Kingston. The neighborhood route has Clifton Avenue hills, passes Hutton Park and offers Catskills views.
Walkers can choose the 5K course that starts and ends at Hudson High School and follows a USATF certified route through residential streets, while a free kids 1 mile borders the Hudson Fireman's Home and Museum. Entry is free for those 17 and..
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.
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