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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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ARF’s Stroll to the Sea Dog Walk

October 11 @ 09:00 AM - October 11 @ 12:00 PM
Mulford Farm, 10 James Lane, East Hampton, NY
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Family Drip Painting Workshop

October 11 @ 10:00 AM - October 11 @ 11:30 AM
830 Springs Fireplace Rd, East Hampton, NY 11937
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Free Family Fun: 26th Annual Long Pond Greenbelt Celebration

October 11 @ 10:00 AM - October 11 @ 01:00 PM
SOFO Museum, 377 Bridgehampton/Sag Harbor Turnpike
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CMEE’S Big Birthday Bash!

October 11 @ 10:00 AM - October 11 @ 12:00 PM
376 Bridgehampton-Sag Harbor Turnpike, Bridgehampton, NY 11932
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Chowdah Chowdown – to benefit Springs Food Pantry

October 11 @ 12:00 PM - October 11 @ 03:00 PM
Springs Tavern and Grill, 15 Fort Pond Blvd, East Hampton, NY 11937
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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

  • Grab your furry friend and take a stroll to Main Beach with ARF!

Check out the Top Hamptons Events This Weekend!

🐾 ARF’s Stroll to the Sea Dog Walk
📅 When: Saturday, October 11, 2025 | 9AM–12PM
📍 Where: Mulford Farm, 10 James Lane, East Hampton, NY

Enjoy vendors, contests, and giveaways before strolling to Main Beach.

🥣 Chowdah Chowdown
📅 When: Saturday, October 11, 2025 | 12PM–3PM
📍 Where: Springs Tavern and Grill, 15 Fort Pond Blvd, East Hampton, NY

All-you-can-eat chowder and soup from 20 local chefs, plus live music and a mocktail bar — all to benefit the Springs Food Pantry!

🍺 SagtoberFest
📅 When: Sat, Oct 11 – Sun, Oct 12, 2025 | 12PM–8PM
📍 Where: Kidd Squid, 11 Spring St, Sag Harbor, NY

Celebrate Oktoberfest Sag Harbor–style! Enjoy bratwurst, pretzels, oysters, pumpkin stew, and live music by Jon Divello, Woody Boley, Greg McMullen & Jake Lear.

🎬 33rd Hamptons International Film Festival
📅 When: Thurs, Oct 9 – Mon, Oct 13, 2025 | 9AM–10PM
📍 Where: Various Locations

The 33rd edition of HIFF brings a world-class lineup of narrative and documentary films, features, and shorts from around the globe. 

🍪 Levain Bakery: Book Talk & Signing
📅 When: Saturday, October 11, 2025 | 12PM–1PM
📍 Where: BookHampton, 41 Main Street, East Hampton, NY

Meet Levain Bakery cofounders Pam Weekes & Connie McDonald and grab their new book.

🌿 26th Annual Long Pond Greenbelt Celebration
📅 When: Saturday, October 11, 2025 | 10AM–1PM
📍 Where: SOFO Museum, 377 Bridgehampton–Sag Harbor Tpk, Bridgehampton, NY

Enjoy games, crafts, guided walks, face painting, and ice cream!

🎉 CMEE’s Big Birthday Bash!
📅 When: Saturday, October 11, 2025 | 10AM–12PM
📍 Where: SOFO, 376 Bridgehampton–Sag Harbor Tpk, Bridgehampton, NY

Join for crafts, treats, dance, and play!

🛋️ Hub Home Grand Opening Party & Open House
📅 When: Friday, October 10, 2025 | 6PM–9PM
📍 Where: HUB Home, 2183 Montauk Hwy, Bridgehampton, NY

Celebrate the grand opening of HUB Home, a curated consignment shop with luxury furnishings, art, and décor.

Check out more events at Hamptons.com (Link in Bio)
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#hamptons #arf #community #stephentalkhouse #dining #hamptonsfilmfestival
  • The 33rd Hamptons International Film Festival kicked off last Friday with the U.S. premiere of A24’s Eternity starring Elizabeth Olsen, Miles Teller, and Callum Turner.⁠
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Elizabeth Olsen attended the premiere on Friday, and on Saturday sat down with IndieWire’s Editorial Director Kate Erbland at the Sag Harbor Cinema as a part of the festival’s “A Conversation With” series. Later that day, the second “A Conversation With” took place as Ethan Hawke and moderator Alison Stewart talked about Blue Moon, as well as Hawke’s filmography. ⁠
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Sydney Sweeney received the festival’s Achievement in Acting Award following the U.S. premiere of her film Christy in East Hampton. ⁠
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Notable Guests included: Alessandro Nivola, Alec Baldwin, Amanda Peet, Tonatiuh, Miriam Shor, Lois Smith, Tim Blake Nelson, Mareille Enos, Bob Balaban, E. Jean Carroll, Roberta Kaplan, Ellen Barkin, Bernie Telsie, Bill Condon.⁠
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📸: Jess Dalene⁠
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#hiff #hamptonsinternationalfilmfestival #film #elizabetholsen #sydneysweeney #hamptons #hamptonsfilm⁠
  • When: Fri, Oct 3rd – Sun, Oct 5th, 2025
8am – 5pm

Where: Levain Bakery, 354 Montauk Hwy, Wainscott, NY

Levain Bakery is introducing a new cookie for a limited time: Peanut Butter Dark Chocolate Chip – a decadent mix of creamy and chunky peanut butter with rich dark chocolate chunks. Originally created to celebrate the opening of Levain’s Beverly Hills Bakery, this indulgent new flavor will now be available for just three days only, October 3–5, at all retail bakery locations.

To make the weekend even sweeter, guests who purchase a cookie will receive a Levain Bakery mini tote (while supplies last), a fan-favorite collectible sure to go quickly.

#levain #levainbakery #cookie #minitote #tote #hamptons
  • From world premieres at the Hamptons International Film Festival to SouthamptonFest! ⁠
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Check out the Top Hamptons Events This Weekend!⁠
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🎬 33rd Hamptons International Film Festival⁠
📅 Oct 3 – 13, 2025 | 9AM – 10PM⁠
📍 Various Locations⁠
A global lineup of films, shorts & documentaries.⁠
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🍪 Levain Bakery⁠
📅 Oct 3 – 5, 2025 | 8AM – 5PM⁠
📍 354 Montauk Hwy, Wainscott⁠
Try the Peanut Butter Dark Chocolate Chip cookie + snag a mini tote (while supplies last).⁠
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🎉 13th Annual SouthamptonFest⁠
📅 Oct 3 – 5, 2025 | 10AM – 7PM⁠
📍 Southampton Village⁠
Arts, culture, food & family fun all weekend long!⁠
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🎶 SpringsFest⁠
📅 Oct 4, 2025⁠
📍 1 Parsons Pl, East Hampton⁠
Live music, raffles, crafts, blacksmith demos & more.⁠
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💃 Salsa Social @ The Clubhouse Hamptons⁠
📅 Oct 4, 2025 | 9PM – 11:30PM⁠
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Dance the night away w/ DJ Chile & more!⁠
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🐚 34th Annual Largest Clam Contest⁠
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Taste clam chowder, clam pies & cheer on the winners!⁠
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🎷 East Meets West Jazz Jam Session⁠
📅 Oct 5, 2025 | 2PM – 5PM⁠
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✨ Which event are you most excited for?⁠
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  • So many fun fall activities in the Hamptons 🎃

@fairviewfarmatmecox 
@corwithsfarmstand 
@milkpailfarmorchard 

Check out our fall guide at Hamptons.com (Link in Bio)

#hamptons #fall #applepicking🍎 #pumpkin #maze #pettingfarm
  • As summer winds down and the cool breezes of fall approach, jewelry enthusiasts and fashion lovers alike are looking for the latest seasonal trends. Yael Fraynd, founder and president of Yaya Publicity, offers an insider’s perspective on what to expect this fall — especially for those embracing the chic lifestyle of the Hamptons.⁠
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Looking ahead to fall, Fraynd described the evolving styles with enthusiasm. For fall, expect to see bold statement pieces, rich gemstone colors like orange and a playful mix of metals. ⁠
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She also noted the influence of pop culture on jewelry trends, including celebrities like Taylor Swift, who is recently engaged, saying, “It could also be just, you know, with Taylor Swift, who has such a big effect on what people like.”⁠
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On the seamless transition from summer to fall styles, she observed, “In the summer, you see a bit of Western-inspired pieces, and I think that they really do kind of transition into fall really nicely. ⁠
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