Pine Plains
Walking Events Calendar near Pine Plains 2026-2027
Monthly updates for Pine Plains
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Explore the top walking events near Pine Plains for 2026-2027! We've gathered 17 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..
At Jug End State Reservation in Egremont MA walkers follow a 4.2 mile loop through woods and fields. Many laps within 6 hours count but partial laps do not; .75 mile loop opens last hour.
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.
October 2026
Walkers follow a 5K route starting at Chesterwood, 4 Williamsville Rd, Stockbridge MA, alongside the running races. The event offers refreshments and awards and carries a $35 entry fee.
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 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 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 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.
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.
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..
May 2027