The oldest ranch in the country, Deep Hollow dates back to the late 1600s, a time when ranching was common on Long Island. The ranch's rich centuries-long history is rumored to include visits from Teddy Roosevelt and the Rough Riders and buried loot

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The oldest ranch in the country, Deep Hollow dates back to the late 1600s, a time when ranching was common on Long Island. The ranch's rich centuries-long history is rumored to include visits from Teddy Roosevelt and the Rough Riders and buried loot from Captain Kidd. If your kids aren't fascinated by that bit of trivia, they'll love petting the donkeys and ponies that live at the ranch.

With its 3,000 acres of rolling hills and beaches, in addition to riding trails, the Deep Hollow Ranch is fun for both experienced horsemen and beginners (including small children). Offering trail rides in small groups, the ranch offers horses to match a variety of ability levels. You can also reserve a private guided ride if your group needs a little more personal attention. Since Deep Hollow is run by experienced ranchers with many generations of ranching in their blood, you'll be in good hands.

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