Deep Hollow Ranch
Experience the thrill of horseback riding along Montauk's stunning coastline at the oldest working ranch in the USA.
Highlights
Must-see attractions
Social
From TikTok & Reddit
Best Time
Quieter trails, cooler temps
Deep Hollow Ranch
Best Time
Quieter trails, cooler temps
Highlights
Must-see attractions
Experience the thrill of horseback riding along Montauk's stunning coastline at the oldest working ranch in the USA.
"An absolute must-visit for an amazing experience with well-trained horses and professional staff."
📞 Call for Reservations
Booking ahead is wise, especially for longer rides. Call 631-668-2744 to secure your spot.
⚖️ Be Mindful of Weight Limits
Ranch has a weight limit for horse safety, typically around 240 lbs.
Highlights
Discover the most iconic attractions and experiences
Oceanfront Trail Rides
Along the coast
Experience breathtaking ocean views and the sound of waves on a guided horseback ride along the beach.
Historic Ranch Experience
The ranch grounds
Step back in time at the oldest working ranch in the US, established in the mid-1600s.
Well-Trained & Gentle Horses
Trail rides
Enjoy your ride on responsive, well-cared-for horses suitable for riders of all experience levels.
Plans like a pro.
Thinks like you
Planning Your Visit
Weight Limits & Horse Welfare
Book in Advance for Peak Times
Best Times
Insider Tips
from TikTok, Instagram & Reddit
📞 Call for Reservations
Booking ahead is wise, especially for longer rides. Call 631-668-2744 to secure your spot.
⚖️ Be Mindful of Weight Limits
Ranch has a weight limit for horse safety, typically around 240 lbs. +1
🐴 Beginner Friendly
Staff are helpful and explain everything, making it great for first-time riders.
📸 Capture the Views
The oceanfront trails offer stunning photo opportunities.
Tips
from all over the internet
📞 Call for Reservations
Booking ahead is wise, especially for longer rides. Call 631-668-2744 to secure your spot.
⚖️ Be Mindful of Weight Limits
Ranch has a weight limit for horse safety, typically around 240 lbs. +1
🐴 Beginner Friendly
Staff are helpful and explain everything, making it great for first-time riders.
📸 Capture the Views
The oceanfront trails offer stunning photo opportunities.
🤠 Embrace the Cowboy Spirit
Experience the charm of the oldest working ranch in the USA.
What Travellers Say
Reviews Summary
Visitors consistently praise Deep Hollow Ranch for its beautiful oceanfront trails and the exceptional care and training of its horses. The staff are frequently highlighted for their kindness, professionalism, and helpfulness, making it a memorable experience for riders of all levels. Some guests have noted the ranch's weight restrictions, which are in place for horse welfare.
"We went on the 90 minute ride with the beach and it was a blast! The employees were very nice, our guide was sweet and friendly. Will definitely go again!"
Alexandra Levinson
"First time on a horse, i was a bit nervous at first but the staff were super helpful and explained everything! Trail was great! Such a great time one of the most memorable parts of our weekend getaway!"
Eklorida Vucaj
"Every time we come to Montauk, a visit to Deep Hollow Ranch is an absolute must! We’ve gone multiple times now, and it’s always an amazing experience. The horses are perfect so well trained, gentle, and responsive. You can tell they’re cared for with love and expertise.
The staff is consistently kind, patient, and professional, making the entire experience relaxing and fun from start to finish. A special shout-out to the guide who always leads our trail rides, he’s from Jamaica and he’s truly the BEST! Friendly, knowledgeable, and great with both the horses and riders. Highly recommend to anyone visiting Montauk, whether you’re a beginner or an experienced rider!"
Erica U
What People Like
What People Dislike
Frequently Asked Questions
🚇 🗺️ Getting There
Deep Hollow Ranch is located in Montauk, New York. Driving is the most common way to reach it. Parking is available on-site. If using GPS, input 'Deep Hollow Ranch, Montauk, NY'.
Public transport options to Montauk can be limited, especially for reaching the ranch directly. It's advisable to check local bus schedules or consider ride-sharing services once you are in Montauk.
Many visitors drive to Montauk. During peak season, traffic can be heavy. Consider visiting on a weekday or during shoulder seasons for a smoother journey.
🎫 🎫 Tickets & Entry
Deep Hollow Ranch prices vary depending on the duration of the ride. While specific prices aren't always listed online, expect to pay for the length of your trail ride. It's best to call for current pricing.
Reservations are highly recommended, especially for longer rides or during peak season, to ensure availability. You can call the ranch directly to book your horseback riding experience.
Deep Hollow Ranch is typically open daily for trail rides. It's always a good idea to call ahead or check their social media for the most up-to-date operating hours, especially outside of peak summer season.
Yes, Deep Hollow Ranch enforces weight limits for the safety and well-being of their horses, generally around 240 pounds. It's important to be aware of this policy before booking. +1
While not explicitly stated, inquiring directly with the ranch about private tour options might be possible, especially for special occasions.
🎫 🧭 Onsite Experience
Deep Hollow Ranch offers scenic trail rides, including popular options that go along the oceanfront and beach, providing beautiful views. 
Absolutely! The horses are described as well-trained, gentle, and responsive, making them suitable for riders of all experience levels, including beginners. [^Review]
Comfortable clothing and closed-toe shoes are recommended for horseback riding. Avoid loose items that could get caught.
Yes, the scenic trails, especially along the ocean, offer fantastic photo opportunities. However, be mindful of your surroundings and the horse's comfort while taking pictures.
Yes, Deep Hollow Ranch is historically the oldest working cattle ranch in the United States, established in the mid-1600s.
🍽️ 🍽️ Food & Dining
Information on on-site food options is limited. It's advisable to bring your own snacks and drinks or plan to dine at nearby restaurants in Montauk after your ride.
While not explicitly stated, it's generally acceptable to bring personal snacks and water, especially for longer visits. Check with the ranch if you have specific concerns.
📸 📸 Photography
The oceanfront trails and beach areas offer the most picturesque backdrops for photos. The historic ranch buildings also provide a unique setting.
Drone usage policies can vary. It's best to check with the ranch or local park regulations regarding drone operation before flying.
For Different Travelers
Tailored advice for your travel style
👨👩👧 Families with Kids
💑 Couples & Romantic Getaways
+1 The ranch's historic charm adds to the ambiance, providing a step back in time for a truly special outing. It's a perfect activity for couples looking to create lasting memories in a beautiful setting. [^Review]🐎 Experienced Riders
Deep Dives
In-depth insights and expert knowledge
The History of Deep Hollow Ranch
+1 This rich heritage means that when you visit, you're not just going for a horseback ride; you're stepping onto grounds that have been active for centuries, witnessing the evolution of the East End. The ranch continues to operate as a working cattle ranch, preserving a piece of the American cowboy spirit on the East Coast. Concessionaires Patrick and Cate Keogh have been managing the ranch since 2010, continuing its legacy.
The ranch offers a unique blend of living history and outdoor recreation, making it a compelling destination for those interested in both equestrian activities and historical exploration. The very land itself tells a story of resilience and tradition. Understanding Horseback Riding Policies
It's important for visitors to be aware of and respect these guidelines. The ranch's commitment to their horses' well-being is a testament to their dedication to responsible animal husbandry.
Experiencing Montauk's Coastal Trails
+1 This combination of equestrian activity and natural beauty makes for an unforgettable experience, often cited as a highlight by visitors. [^Review]Beyond the ranch's immediate trails, the surrounding area also offers beautiful natural landscapes. Amsterdam Beach State Park, located across from Deep Hollow Ranch, features trails winding through holly trees and dunes, leading to quiet, beautiful beaches.
This proximity allows visitors to combine their ranch visit with further exploration of Montauk's unspoiled natural beauty, making for a well-rounded coastal adventure.
Social
from TikTok, Instagram & Reddit