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October 23, 2021

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

T.J. Clementeby T.J. Clemente
in Community, Trending
Home Community

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 27th and October 29th. 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. 

 

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INTERVIEW: Antonella Bertello Talks The Baker House 1650, 2021 Peru to the World Expo, and Marina Coast

INTERVIEW: Antonella Bertello Talks The Baker House 1650, 2021 Peru to the World Expo, and Marina Coast

  • Whether you are walking the fast-paced streets of New York City or taking a leisurely beach stroll in the Hamptons, there’s a slight chance you might run into Elias Friedman, known online as “The Dogist.” His adoration of dogs, combined with his passion for photography, has led him to gain over 7 million followers on Instagram. The audience at his recent Guild Hall show reflects how much people truly love their dogs and how Elias does so much more than simply take picture-perfect dog portraits. He can capture the beautiful bond between man and his best friend. His book, This Dog Will Change Your Life, is already a New York Times bestseller. Guild Hall’s lobby was filled with fans excited to get their copy signed.⁠
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His guests included local dog lovers and friends of ARF (Animal Rescue Fund of the Hamptons). Attendees had front-row seats to a “Dogist”-style encounter: a casual conversation about how the dog entered the owner’s life, followed by a quick photo shoot revealing Elias’ methods for capturing the dog’s attention (hint: It’s dog noises and treats).⁠
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I had the pleasure of talking to Elias about how “The Dogist” came to be, rescue organizations, and the Hamptons.⁠
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Let’s go back to the beginning. What inspired you to dive into photography?⁠
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We had a dark room because my dad was an amateur photographer, and I’d always liked cameras and gadgets. We had a couple of Labrador retrievers who were sort of my first muses and would happily sit for pictures. I was taking dog pictures from a young age and then fast forward to 2012 in New York City I was let go from my job and saw what other street photographers were doing like Humans of New York and The Sartorialist and thought why isn’t someone doing that for dogs and I thought I wanted to be the person, I dusted off my camera and the rest is kind of history. It took off pretty quickly because it turns out people like dogs just as much as I do.⁠
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Read the full interview at Hamptons.com (Link in Bio)⁠
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#dogist #arf #dogs #animalrescue #guildhall #hamptons
  • 167 Dune Road, Bridgehampton, NY 11932⁠
Saunders Exclusive: $42,500,000⁠
@jenniferwilsonhamptons 
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Experience extraordinary coastal living with this exquisite oceanfront estate on Dune Road in Bridgehampton. ⁠
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Designed by the renowned architect Francis Fleetwood, this remarkable property boasts 300 feet of private ocean frontage, complete with its own private boardwalk leading directly to the beach, all set on over 3 acres of prime land.⁠
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The charming shingle-style residence encompasses 4,200 +/- sq. ft. of luxurious living space, featuring 5 bedrooms and 5 full bathrooms, plus an additional half bath.⁠
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Read the full article at Hamptons.com (Link in Bio)⁠
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#duneroad #oceanfront #bridgehampton #realestate #hamptons #francisfleetwood ⁠
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  • The Hamptons have seen their fair share of collaborations and takeovers this summer. Still, nothing compares to The h.wood Group and Chase Sapphire Reserve’s transformation of Montauk hotspot Mary Lou’s into Delilah Montauk.⁠
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The four-day takeover combined unforgettable dining experiences with show-stopping live entertainment featuring performances by Zack Bia, Alesso, Gwen Stefani, and DJ Pee.Wee (Anderson Paak). ⁠
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Exclusively for Chase Sapphire Reserve cardholders, diners were treated to white glove hospitality and Delilah’s staples, including the famous chicken tenders and tuna tartare, and bold twists on Hamptons classics like lobster rolls, striped bass crudo, and crab and avocado toast. 

Check out more at Hamptons.com (Link in Bio)

#gwenstefani #alesso #djpeewee #chasesapphirereserve #delilahmontauk #montauk #hamptons
  • LVIS thrift shops are open Tuesdays through Saturdays 10 AM through 5 PM

donations are accepted Wednesday through Saturday 10 AM through 1 PM by appointment 

located at 95 Main St East Hampton
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☕ Cars & Coffee⁠
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Classic & exotic cars, food, drinks & live music.⁠
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🛍 Hampton Vintage⁠
📅 Sun, Sept 14 | 10AM–5PM⁠
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Shop unique vintage finds!⁠
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🎶 Hamptons Festival of Music Finale⁠
📅 Sun, Sept 14 | 4PM⁠
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🍷 Wine Dinner with Pradorey at R.AIRE⁠
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🎥 Toy Story 30th Anniversary Screening⁠
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#carshow #hamptons #sangennaro #sangennarofeast #winedinner #bridgeIX
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