Sixty-Something: Deep Thoughts About Montauk’s The Deep Hollow Ranch

There are things one never forgets. For me, one of those things was the time I brought my daughters to the famous Deep Hallow Ranch in Montauk for a late October horseback ride. Their birthdays are October 27^th and October 29^th. I had promised them during our summer visit to Montauk we would return for a birthday ride when it was cooler and more pleasant. 

The Deep Hollow Ranch is embedded with so much history. Years back I tried to capture it in an 800-word article for a free weekly and had to leave out perhaps 3000 words of facts. 

The Deep Hollow Ranch was established in 1658. When I wrote my articles it was owned by Rusty Leaver and his wife, whose family had owned the ranch for generations. I remember having breakfast with them in their kitchen that had a view of the horses and cattle grazing when I was factfinding a story about the ranch. The ranch is billed as the oldest working Cattle Ranch in the United States. There was a time when the animals of the ranch actually continually fed the occupying British Army and Navy stationed in East Hampton and out in Gardiner’s Bay during the American Revolution. Then there are the Teddy Roosevelt Rough Riders stories and that part of its history. Today it is no longer privately owned and is part of the Suffolk County Parks. 

It was a crisp October Saturday when I brought the girls out for the birthday ride. We had left Pelham Manor, NY very early and arrived at the ranch in time for our scheduled noon ride. We had stopped at the then-in-business Princess Diner in Southampton on Route 27 for a snack and of course a bathroom break. Our family had spent the previous winter vacation on a dude ranch in Tucson where we all rode horses a few times every day. The girls had their western gear on and were excited. No matter how many times you take the Deep Hollow Ranch trail ride when you come out of the woods and ride slowly on the sand by the ocean and Block Island Sound, the breeze, the view, and the feeling is special. Riding the trails in the fall season also has the leaves thinned out so you see the deer, the birds, and of course the cattle, whereas in the summer not as well. 

The guided ride entails pleasant hills and open spots where the horses know to safely gallop and then slow down for the approaching narrow passages. Just writing about it makes me want to take my sixty-something body back out there for another ride! 

I am sure many Montauk locals remember when Showtime was filming the series, “The Affair,” and used the ranch as the home of the Lockhart family. In “The Affair,” the ranch had been in the fictional Lockhart family for many generations. For a while, the iconic “Deep Hollow Ranch” sign was actually replaced with a similarly designed sign that read “Lockhart Ranch.” 

Strangely I was preparing for a trip this week to Key West Florida and searching for an old Hawaiian-type shirt to wear down there when out the storage chest in the basement came the two small-sized dark-green “Deep Hollow Ranch” tee-shirts I bought the girls that day. It’s funny as we age what items get randomly lost and saved. Such moments always make one take a pause and think back to that day that item was purchased. The excitement the girls had to get it. 

Amazingly the ranch still offers 90-minute rides for kids ages 6 and up as well as adults. The rides schedule although reduced due to Covid-19 is still a wonder of Montauk only those in the know partake. It is always amazing to me taking a ride on those Montauk trials. I can’t help but think back to the Montaukett Indians who probably formed many of these trails with their foot traffic. This section of unspoiled Montauk topography is there for viewing via horseback. Hopefully, someday my one-year-old granddaughter when she is of age will ride the trails with her mom who will recall riding the trail with me her dad.