COLUMNS

Horseback Riding in Montauk on Trails Leading to the Past
by Jenny Michaels

Deep Hollow Ranch, located on thousands of beautiful acres on Theodore Roosevelt County Park, is a premier ranch as well as the oldest ranch in the country. This vast, historic rich property is ideally suited for enjoying the scenery and the outdoors on horseback. Over the weekend, my three friends and I decided to go horseback riding. Knowing how beautiful the trails are, I thought a ride at Deep Hollow would be a perfect ending to a fabulous weekend. We made our reservation with Diane, a fifth generation descendent of the Dickenson family, who has managed the ranch since the 1800s. As we arrived for our 10:00 am ride, we were warmly greeted by Pedro, a miniature Sicilian donkey, who was casually roaming the grounds posing for pictures with those preparing to go on a trail ride. We saddled up our horses and off we went walking through the ranch. Teddy Roosevelt and his Rough Riders had set up camp at Deep Hollow after returning from the Spanish American War. It is rumored that Captain Kidd may have buried treasure in Money Pond, near the ranch. Both allowed us to think about and reflect a bit at these historical pieces of the past and the part both played in Montauk's early days.

The landscape along the trails has a dramatically beautiful quality and at times, through the patches of shade and warmth from the sunlight, provides the feeling of serenity. There we were, all seven of us in total, relaxed and enjoying this extraordinary ride, winding through the wilderness. It was a perfect day. I have been on this trail before and knew what to expect, however I knew my friends would be in for a pleasant surprise. They were not aware that the excursion included riding along the beach. Coincidentally, riding along the beach had been a dream of one of my friends that joined us that day. As we slowly crept up the hill, we arrived at an expansive view of the ocean, Block Island, the Light House and lots in between. It was gorgeous! We quickly took out our cameras and began taking photos of everything and anything. We would later swap pictures and use the best one to put in a frame as a memory from our weekend. It really was spectacular. The horses slowly walked down the hill to the beach and had a chance to ride along the shoreline. This was another great photo opportunity. Since all of us were at different riding levels, it was great that the ride was able to accommodate riders of all skill levels. Both advanced and beginner riders can experience these great trails on well-trained, friendly horses.

Located 110 miles outside of New York City, Deep Hollow offers all the services of a full working ranch, with a staff of professional riders and guides with years of experience, insuring your enjoyment and safety during your visit. Deep Hollow also offers a one-day, fun-filled learning experience for students. Students and teachers are transported back in time by horse drawn wagon and given an educational experience involving cowboys, Indians, horses, cattle, Captain Kidd, and Teddy Roosevelt. This event is an enjoyable day of living history.
Do not forget to bring your camera. Spectacular views from the highest point in Montauk, overlooking Long Island Sound, provide magnificent photo opportunities that help make your experience at Deep Hollow Ranch unforgettable.

For more information visit www.deephollowranch.com or call 631-668-2744

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