Horseback riding in Montauk

Deep Hollow Ranch is run by Patrick and Catherine Keogh, both with deep ties to ranching and to Montauk. Montauk born and bred and “horse crazy” as long as she can remember, Cate worked for years at the Ranch under Rusty and Diane Leaver, and the Leavers hired Patrick after he’d been working rodeos in Colorado. “Rusty and Diane were convinced Pat and I should meet,” Cate chuckles. “The rest is history.” When given the opportunity to take over the management of the Ranch, the Keoghs jumped at the chance to continue to provide Montauk with an authentic working ranch. Says Cate, “Deep Hollow is a place where someone who’s never been on a horse can feel comfortable riding through the same historic land where the Montauketts and early settlers lived and worked.”

The Keoghs’ mission is simple: provide an environment where friends and families can put down their electronic devices, laugh, and spend quality time with each other in Montauk’s pristine natural settings. Join a trail ride guided by a real cowboy or cowgirl up to Squaw Hill and overlook an incredible vista of Oyster Pond.  Finish up on the beach with a glorious view of the Block Island Sound. If you are lucky, you might spot the great horned owl “the size of a small child,” which has taken up residence near the barn. Groups are small and all levels of riders are welcome. For children six and older, half-hour trail rides are available. For those who prefer to do their touring off the saddle, the Ranch also offers wagon tours of the pasturelands. 631-668-2744 deephollowranch.com