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Walking Events Calendar near Rhinebeck 2026-2027

Monthly updates for Rhinebeck

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

Explore the top walking events near Rhinebeck for 2026-2027! We've gathered 13 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..
12K, 25K and 50K walks at Macedonia Brook State Park on single track forest trails with steep climbs and views; aid stations supply water, snacks; walkers carry own cup.
Walkers can take part in the 5K course that starts and finishes at Kent Town Hall, 41 Green Blvd, Kent CT. Packet pickup is available on race day and the event includes both walking and running categories.
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.
Walkers follow a 3.10686 Miles route that starts on the baseball field track at Mount Saint Mary College Campus in Newburgh, NY, loops twice through campus with Hudson River views; pre registration is $25.
October 2026
Walkers complete the 5K course via two loops of the Lime Rock Park circuit in Lakeville CT. The venue provides public restrooms and a water station at start and finish, and wheelchairs and disabled push strollers are welcomed.
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.
May 2027
Walkers can choose 50 mile or 26.2 mile routes across Shawangunk carriage roads, forests and ridgelines with closely spaced aid stations and an 18 hour cutoff.
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