Circle B Ranch Adirondack Sleigh Rides
Keep the jingle bell spirit going all Winter long with a horse-drawn sleigh ride at Circle B Ranch in Chestertown.
Editor’s note (updated 2026):
Looking for the most up-to-date guide to winter sleigh rides at Circle B Ranch in Chestertown? Read our refreshed article here → Circle B Ranch 2026
Nothing evokes old-fashioned Christmas and Winter Festival vibes more than a horse-drawn carriage across snowy hills and valleys. If your visions of dancing sugar plums are bumping up against dreams of dashing through the snow, Circle B Ranch in Chestertown has you covered.
Photos courtesy Circle B Ranch
Circle B stands on pristine land in the middle of 3,000 acres of wilderness. The property has been in continuous use since the 1800s. First as a farm and then as a ranch, with almost no development, with the exception of improvements made by the owners. They offer visitors a wonderful opportunity to take in the pristine beauty of wintertime in the Adirondacks.
Guests can opt for Group Sleigh Rides with their Belgian Draft Horse team, Jack and Daniels. See what they did there? We did, too. Anyway, they will take you on a picturesque tour through forests and fields. The sleigh accommodates up to 12 people on cushioned bench-style seats. Anyone can sign up for the Group Ride or book the whole shebang for a private tour with friends and family.
Private sleigh rides are available, too. In 2021, they added a custom group sleigh, pulled by Percheron Draft Horses, Jake and Charlie. The sleigh features leatherette seating, perfect for groups of up to seven people.
For a more intimate ride, their brand new 2022 custom vis-à-vis sleigh, pulled By Belgian Draft Horse, Jethro, features two luxury velvet-clad benches that face each other, accommodating up to four people.
Circle B makes it easy for you to book your ride online. For more information, visit their website.
Find places to eat, stay, shop and things to do near Circle B Ranch.
Shop for unique Adirondack gifts.
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A virtual educational event, presented by the Adirondack Center for Loon Conservation (ACLC).
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