Gabrielle Payne, a lifelong horse enthusiast and niece of Deep Hollow Ranch’s concessionaire Cate Keogh, expertly guided a group of novice riders, including the author, on a scenic horseback trail and beach ride in Montauk. Payne’s calm demeanor and deep connection with the horses helped ease the nerves of inexperienced riders as they explored the ranch’s beautiful landscape, from ridges overlooking meadows to sandy beaches by Oyster Pond and Block Island Sound. Each horse had a distinct personality, with Payne thoughtfully pairing riders to suitable mounts and leading the group confidently on the 90-minute journey.

The ride offered both challenges and memorable moments, such as managing horses’ reactions to flies, navigating rocky terrain, and experiencing the thrill of trotting along the trail. Despite some initial apprehension and the physical demands of horseback riding, the author found the experience rewarding and unforgettable. The day ended with a sense of accomplishment and a newfound appreciation for the skill and bond involved in trail riding, inspiring the author to continue seeking new adventures.