Subscribe to Guide
No Result
View All Result
Hamptons.com
  • Spotlight Magazine
  • Lifestyle
    • Featured
    • Entertainment
    • Arts
    • Community
    • Dining
    • Recreation
    • Trending
  • Events
    • Events Calendar
    • Post an Event
    • Gallery
  • Real Estate
    • Real Estate Features
    • Search Real Estate
      • Open Houses
      • Search Sales
      • Search Rentals
    • Title Insurance
    • Happening In The Hamptons Podcast
  • Live Cameras
    • All Live Cameras
    • Live Weather Cams
    • Amagansett, Atlantic Avenue Beach
    • Bridgehampton, West Scott Cameron Beach
    • East Hampton Village, Main Beach
    • East Hampton Village, Main Street
    • East Hampton Village, Newtown Lane
    • Hampton Bays, Ponquogue Beach
    • Hampton Bays, Ponquogue Bridge
    • Hampton Bays, Shinnecock Fishing Dock
    • Hampton Bays, Tiana Beach
    • Long Island Aquarium | Coral Reef
    • Long Island Aquarium | Penguins
    • Long Island Aquarium | Shark Tank
    • Montauk, Downtown Circle
    • Montauk, Lars Simenson Skatepark
    • Montauk, Gin Beach & Inlet
    • Montauk, Sunset Beach & Inlet
    • Sagaponack, Sagg Main Beach
    • Sag Harbor, Foster Memorial Beach
    • Sag Harbor, Long Wharf Marina
    • Sag Harbor, Main Street (South)
    • Sag Harbor, Windmill Beach & Bay
    • Shelter Island, South Ferry
    • Southampton, 39A to Montauk Hwy Merge
    • Southampton, Conscience Point Marina
    • Southampton Village, Coopers Beach
    • Southampton Village, Main Street (South)
    • Southampton Village, Main Street (North)
    • Southampton Village, Main Street (Hildreths)
    • Westhampton Village, Main Street (East)
    • Westhampton Village, Rogers Beach
  • Public WiFi
    • Public WiFi Map
    • Public Wi-Fi Support
  • Spotlight Magazine
  • Lifestyle
    • Featured
    • Entertainment
    • Arts
    • Community
    • Dining
    • Recreation
    • Trending
  • Events
    • Events Calendar
    • Post an Event
    • Gallery
  • Real Estate
    • Real Estate Features
    • Search Real Estate
      • Open Houses
      • Search Sales
      • Search Rentals
    • Title Insurance
    • Happening In The Hamptons Podcast
  • Live Cameras
    • All Live Cameras
    • Live Weather Cams
    • Amagansett, Atlantic Avenue Beach
    • Bridgehampton, West Scott Cameron Beach
    • East Hampton Village, Main Beach
    • East Hampton Village, Main Street
    • East Hampton Village, Newtown Lane
    • Hampton Bays, Ponquogue Beach
    • Hampton Bays, Ponquogue Bridge
    • Hampton Bays, Shinnecock Fishing Dock
    • Hampton Bays, Tiana Beach
    • Long Island Aquarium | Coral Reef
    • Long Island Aquarium | Penguins
    • Long Island Aquarium | Shark Tank
    • Montauk, Downtown Circle
    • Montauk, Lars Simenson Skatepark
    • Montauk, Gin Beach & Inlet
    • Montauk, Sunset Beach & Inlet
    • Sagaponack, Sagg Main Beach
    • Sag Harbor, Foster Memorial Beach
    • Sag Harbor, Long Wharf Marina
    • Sag Harbor, Main Street (South)
    • Sag Harbor, Windmill Beach & Bay
    • Shelter Island, South Ferry
    • Southampton, 39A to Montauk Hwy Merge
    • Southampton, Conscience Point Marina
    • Southampton Village, Coopers Beach
    • Southampton Village, Main Street (South)
    • Southampton Village, Main Street (North)
    • Southampton Village, Main Street (Hildreths)
    • Westhampton Village, Main Street (East)
    • Westhampton Village, Rogers Beach
  • Public WiFi
    • Public WiFi Map
    • Public Wi-Fi Support
No Result
View All Result
Hamptons.com
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. 

 

Sign up for our weekly newsletter!

Get the top Hamptons events and latest scoop!

What's Happening in the Hamptons

Related Posts

The Palm Tree Music Festival
Entertainment

Top Hamptons Events This Weekend: June 20th, 2025

June 20, 2025
Secret Entrances, Exquisite Sushi, and Sake: An Exclusive Omakase Speakeasy Sushi Experience
Dining

Secret Entrances, Exquisite Sushi, and Sake: An Exclusive Omakase Speakeasy Sushi Experience

June 20, 2025
David Vaughan Photography: Slowing Down the East End
Featured

David Vaughan Photography: Slowing Down the East End

June 20, 2025

Search Articles

No Result
View All Result

LOCAL EVENTS

Events

21
Jun
21
Jun
-
21
Jun

The Female Founders Market Garden Shops at The HUB

June 21 @ 09:00 AM - June 21 @ 06:00 PM
The HUB 2183 Montauk Highway Bridgehampton, NY 11932
21
Jun
21
Jun
-
21
Jun

5th Annual Palm Tree Music Festival

June 21 @ 02:00 PM - June 21 @ 11:00 PM
Shinnecock Indian Territory, Southampton, NY 11968, USA
21
Jun
21
Jun
-
21
Jun

Calm Before the Storm Fundraising Cocktail Party & Art Show

June 21 @ 05:00 PM - June 21 @ 07:00 PM
Sag Harbor Whaling & Historical Museum
21
Jun
21
Jun
-
21
Jun

Opening Reception: “The Ark” – An Exhibition curated by Eric Fischl

June 21 @ 06:00 PM - June 21 @ 07:30 PM
The Church, 48 Madison St., Sag Harbor, NY, 11963
21
Jun
21
Jun
-
21
Jun

Author Talk and book signing: “50 Moments” by Nellie Sciutto

June 21 @ 06:00 PM - June 21 @ 07:30 PM
East Hampton Library
Load more listings
Next Post
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

  • Who’s excited for the Palm Tree Music Festival! ⁠
⁠
Check out the Top Hamptons Events This Weekend!⁠
⁠
🎶 5th Annual Palm Tree Music Festival⁠
📅 Saturday, June 21st | 🕑 2pm – 11pm⁠
📍 Shinnecock Indian Territory, Southampton⁠
🌴 Iconic music + luxury vibes + brand activations.⁠
📸: Rob Rich/SocietyAllure.com ©2025⁠
⁠
🛍️ Female Founders Market at The HUB⁠
📅 Saturday, June 21st | 🕘 9am – 6pm⁠
📍 2183 Montauk Hwy, Bridgehampton⁠
✨ Shop curated female-founded Hamptons brands.⁠
⁠
👡 Dolce Vita Pop-Up in Southampton⁠
📅 June 20–22 | 🕚 11am – 3pm daily⁠
📍 95 Main Street, Southampton⁠
🎨 Art, summer style, and new drops each month!⁠
⁠
👜 Kulson Pop-Up at Sage & Madison⁠
📅 Friday, June 20th | 🕒 3pm – 6pm⁠
📍 31 Madison Street, Sag Harbor⁠
🥂 Sip + shop Kulson’s Summer Capsule Collection.⁠
⁠
🍦 BuddhaBerry x Stocked Pop-Up⁠
📅 Friday, June 20th | 🕛 12pm – 5pm⁠
📍 125 Main St, Sag Harbor⁠
🍪 Salted cookie + froyo collab = YUM.⁠
⁠
👜 Hamptons Handbag Festival⁠
📅 Sunday, June 22nd | 🕙 10am – 5pm⁠
📍 15 Montauk Hwy, East Hampton⁠
👜 From vintage to designer. All price points.⁠
⁠
📚 Author Talk: Nellie Sciutto⁠
📅 Saturday, June 21st | 🕕 6pm – 7:30pm⁠
📍 East Hampton Library⁠
🎬 Hear Hollywood tales + get your book signed!⁠
⁠
🎭 Colin Quinn at WHBPAC⁠
📅 Friday, June 20th | 🕗 8pm⁠
📍 76 Main St, Westhampton Beach⁠
😂 Big laughs with the comedy legend.⁠
⁠
🎶 Ghost-Note at Talkhouse⁠
📅 Saturday, June 21st | 🕗 8pm⁠
📍 Stephen Talkhouse, Amagansett⁠
🔥 Don’t miss this epic jam session.⁠
⁠
🥾 Penny Pond Hike⁠
📅 Sunday, June 22nd | 🕤 9:30am – 11:30am⁠
📍 Meet at Red Creek Rd, Hampton Bays⁠
🌲 A beautiful trail to start your Sunday.⁠
⁠
Check out more events at Hamptons.com (Link in Bio)⁠
.⁠
.⁠
.⁠
.⁠
.⁠
#palmtreemusicfestival #hamptons #colinquinn #hub #dolcevita #weekend
  • Hosted in the Hamptons at Calissa, Ja Rule showed off his mixology skills, livin’ it up and serving craft cocktails from Amber & Opal as the premium whiskey brand launched in the Hamptons. 

@jarule 
@calissahamptons 
@amberopalspirits 

#jarule #whiskey #hamptons #calissa #hamptonsweekend #hamptonsevents
  • 24 Saddle Lane, East Hampton, NY 11937⁠
Saunders Exclusive: $2,795,000⁠
⁠
@hamptonsrealestate ⁠
@jenniferwilsonhamptons⁠
@edbruehl⁠
@edmondzenuni_⁠
⁠
This stunning contemporary home redefines modern living with its clean lines, dramatic vaulted ceilings, and walls of glass that flood the interior with natural light. ⁠
⁠
Fully renovated in 2016, the open-concept living area seamlessly blends indoor and outdoor spaces, creating an entertainer’s paradise.⁠
⁠
Imagine hosting gatherings on the expansive deck overlooking the heated pool and spa, or enjoying more intimate moments in the screened porch.⁠
⁠
Read the full article at Hamptons.com (Link in Bio)⁠
.⁠
.⁠
.⁠
.⁠
.⁠
.⁠
#hamptonsrealestate #easthampton #hamptons #realestate⁠
  • Check out the Top Hamptons Events This Weekend!

🎤 Ja Rule Bar Takeover at Calissa
🗓️ Friday, June 13 | 7–9PM
📍 Calissa, Water Mill
Hip-hop icon Ja Rule takes over the bar to celebrate the launch of his new whiskey, Amber & Opal.
📸 Phillip Faraone/Getty Images for AVA Resort
#calissahamptons #jarule #amberandopal

🍷 Mavericks Montauk Winemaker Dinner
🗓️ Friday, June 13 | 6PM
📍 Mavericks, Montauk
Kick off the Summer Winemaker Dinner Series with Christophe Renard of Domaines Ott.
📸 Photo Credit: Michelle McSwain
#mavericksmontauk #domainesott #winemakerdinner

🌸 Hampton Water Rosé Day Tour
🗓️ Saturday, June 14 | 1–7PM
📍 Bounce Beach, Montauk
Show up in pink and celebrate National Rosé Day with tastings, giveaways & more.
#hamptonwater #roséday #montaukevents

🏃 Beacon of Hope 5K Run/Walk
🗓️ Saturday, June 14 | 9AM
📍 Camp Hero to Montauk Lighthouse
Support awareness and hope on this scenic 5K through Camp Hero.
#beaconofhope5k #montauklighthouse

📚 Book Signing with Julianne Moore & Jesse Eisenberg
🗓️ Saturday, June 14 | 3–4PM
📍 Southampton Playhouse
A special family reading and signing with two stars and authors.
#julianneMoore #jesseeisenberg #southamptonny

🐶 ARF’s Rescues & Rosé
🗓️ Saturday, June 14 | 4–7PM
📍 ARF, East Hampton
Rescue dogs + rosé = summer magic.
#arfhamptons #rescuesandrosé #eastenddogs

🎨 Father’s Day Arts & Crafts Fair
🗓️ Saturday, June 14 | 9AM
📍 Marine Park Drive, Sag Harbor
Shop handmade jewelry, furniture, paintings, home goods, and more.
#sagharborarts #hamptonscraftfair

🍋 Lucky One Lemonade Launch w/ Miss Peaches
🗓️ Saturday, June 14 | 2PM
📍 Shark Bar, Montauk
Meet adoptable dogs and sip dog-lover-approved lemonade.
#misspeaches #southamptonanimalshelter #sharkbarmontauk

🛍️ Alice + Olivia Sip & Shop
🗓️ Saturday, June 14 | 4–6PM
📍 68 Main Street, Southampton
Hosted by Sydney Sadick & Sylvia Hemingway to benefit SAC.
#aliceandolivia #sipandshop #southamptonvibes

🩰 Tiler Peck at Guild Hall
🗓️ Saturday, June 14 | 8PM
📍 Guild Hall, East Hampton
An evening of unforgettable performance and movement.
#tilerpeck #guildhall #easthamptonevents

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

#hamptonsweekend
  • Sydney Sadick, Founder, Editor-in-Chief, and Publisher of Spotlight Magazine has been a lifetime Hamptons goer who has created a platform centered around the community she knows and loves. Spotlight Magazine has strong roots with the East End and is a fresh product in an ever-changing landscape.⁠
⁠
Sydney is a fashion and lifestyle expert who regularly appears on television. She is the author of the memoir and educational guide Aim High, which has received praise and recognition in the fashion space, encouraging individuals to find their unique style and achieve their goals.⁠
⁠
Sydney discussed her background and why she decided to launch Spotlight, how the magazine has evolved and grown, and some upcoming projects she is excited to be involved in ahead of the 2025 summer season. ⁠
⁠
Read the full interview at Hamptons.com (Link in Bio)⁠
.⁠
.⁠
.⁠
.⁠
.⁠
#sydneysadick #hamptons
  • At 55 Long Lane, East Hampton, Share the Harvest Farm is more than just rows of vibrant vegetables and rich soil, but a deeply rooted reflection of compassion and the strength of community. Founded in 2010 by John Malafronte, Ira Bezoza and Peter Garnham, this nonprofit farm was built on a simple but powerful idea, that everyone deserves access to wholesome,  locally grown food.⁠
⁠
For over 15 years, Share the Harvest has partnered with numerous other non-profit organizations to serve members of their community who may be dealing with food insecurity. In a region often associated with luxury and wealth, the farm sheds light on a quieter truth in which many local residents struggle to put healthy food on the table. At its core, Share the Harvest Farm is a place of purpose where every tomato, carrot, and pepper represents the spirit of neighbors helping neighbors.⁠
⁠
Meredith Arm, the Executive Director, and Matthew Quirk, the Farm Director, shared more about the farm’s mission, the challenges they face, and the deep sense of purpose that drives their work each day.⁠
⁠
Read the full article at Hamptons.com (Link in Bio)⁠
.⁠
.⁠
.⁠
.⁠
.⁠
.⁠
#sharetheharvest #community #hamptons #local⁠
⁠
Facebook Twitter Instagram Youtube
Hamptons.com

Saunders Broadcasting Corp.

Phone: 631-613-8440
Email: [email protected]
Facebook: Facebook.com/HamptonsOnline
Twitter: @Hamptons
Instagram: @HamptonsOnline

About Us | Contact Us

Hamptons.com

  • Lifestyle
  • Events
  • Real Estate
  • Live Cameras
  • Public WiFi

Subscribe

Sign up for our weekly newsletter!

Get the top Hamptons events and latest scoop!

© 2025 Hamptons.com | All rights reserved
Saunders Broadcasting Corp.
Terms & Conditions | Privacy Policy | About Us | Contact Us

No Result
View All Result
  • Spotlight Magazine
  • Lifestyle
    • Featured
    • Entertainment
    • Arts
    • Community
    • Dining
    • Recreation
    • Trending
  • Events
    • Events Calendar
    • Post an Event
    • Gallery
  • Real Estate
    • Real Estate Features
    • Search Real Estate
      • Open Houses
      • Search Sales
      • Search Rentals
    • Title Insurance
    • Happening In The Hamptons Podcast
  • Live Cameras
    • All Live Cameras
    • Live Weather Cams
    • Amagansett, Atlantic Avenue Beach
    • Bridgehampton, West Scott Cameron Beach
    • East Hampton Village, Main Beach
    • East Hampton Village, Main Street
    • East Hampton Village, Newtown Lane
    • Hampton Bays, Ponquogue Beach
    • Hampton Bays, Ponquogue Bridge
    • Hampton Bays, Shinnecock Fishing Dock
    • Hampton Bays, Tiana Beach
    • Long Island Aquarium | Coral Reef
    • Long Island Aquarium | Penguins
    • Long Island Aquarium | Shark Tank
    • Montauk, Downtown Circle
    • Montauk, Lars Simenson Skatepark
    • Montauk, Gin Beach & Inlet
    • Montauk, Sunset Beach & Inlet
    • Sagaponack, Sagg Main Beach
    • Sag Harbor, Foster Memorial Beach
    • Sag Harbor, Long Wharf Marina
    • Sag Harbor, Main Street (South)
    • Sag Harbor, Windmill Beach & Bay
    • Shelter Island, South Ferry
    • Southampton, 39A to Montauk Hwy Merge
    • Southampton, Conscience Point Marina
    • Southampton Village, Coopers Beach
    • Southampton Village, Main Street (South)
    • Southampton Village, Main Street (North)
    • Southampton Village, Main Street (Hildreths)
    • Westhampton Village, Main Street (East)
    • Westhampton Village, Rogers Beach
  • Public WiFi
    • Public WiFi Map
    • Public Wi-Fi Support

© 2025 Hamptons.com | All rights reserved
Saunders Broadcasting Corp.
Terms & Conditions | Privacy Policy | About Us | Contact Us