Montauk is known for its beaches, bluffs, fishing, and surf. But seeing this end of Long Island from horseback riding offers a different kind of access to the landscape. Horseback riding lets you explore hidden trails and scenic views.
Guided rides travel through open parkland and toward the shoreline, combining coastal scenery with a piece of Montauk’s ranching history. Whether you are an experienced rider or trying it for the first time, there is a version of the day that fits.
Many visitors find horseback riding a unique way to bond with nature. Whether a novice or an expert, horseback riding in Montauk presents an adventurous option.
Did You Know?
Throughout history, horseback riding has been an integral part of Montauk’s culture, and it continues to be a beloved activity.
Livestock has grazed the ground at Deep Hollow Ranch since 1658, and the ranch describes itself as the oldest working ranch in America.
East Hampton families drove cattle and sheep out to these fields every spring for the better part of three centuries, and the trails you ride today cross the same pasture.
Choose Your Adventure
Horseback riding allows you to enjoy the beauty of Montauk while experiencing the thrill of connecting with these magnificent animals.
Whether you want time near the shoreline, a wooded trail, or an hour of instruction, there is a way to see Montauk from the saddle.
As you traverse the coastline, horseback riding gives you a perspective that few other activities can provide. Embrace the freedom that comes with horseback riding.
Trail rides are a popular choice for those interested in horseback riding. Discover the diverse landscapes while enjoying horseback riding along historical paths.
Beach Rides
For those seeking a more structured experience, consider horseback riding lessons to build your skills and confidence.
Exploring the trails on horseback riding strengthens the bond between rider and horse, enhancing the overall experience.
Follow the trail through open parkland until the ground opens and you are riding along the shore.
Trail Rides
When planning your visit, remember that horseback riding can be enjoyed in various ways, catering to different skill levels.
Move through scrub oak, rolling field, and pond on the same network, without the beach leg.
Deep Hollow Ranch is a top destination for those passionate about horseback riding, offering breathtaking views and guided experiences.
Riding Lessons
Book an hour in a ring with an instructor at a barn in Amagansett, East Hampton, or Riverhead.
The joy of horseback riding is evident as you share moments with fellow riders. Horseback riding is not just an activity; it’s an experience to cherish.
Beach & Trail Rides
Horseback riding in Montauk is a cherished tradition, connecting riders with the region’s rich history.
There is one guided beach ride on the East End, and it runs out of a working ranch rather than a rental operation. Riders are matched to their ability, groups stay small, and the guides work there year-round.
Deep Hollow Ranch | Montauk
Deep Hollow Ranch offers Western-style guided rides that head through the surrounding parkland and toward the water.
The trail portion moves through scrub oak and rolling field, quiet enough that you hear the tack more than anything else. Then the ground opens and you are riding along the shore. For many riders, the shoreline portion is the highlight.
Theodore Roosevelt County Park | Montauk
Still known to most people as Montauk County Park, this is the land the rides cross. The park includes open fields, ponds, wooded stretches, and low-lying hollows leading toward the shoreline. Deer are common here, especially in quieter hours.
Local Tip
Ride schedules shift with the season and the earliest slots go first. Call ahead rather than turning up, and wear long pants and shoes that cover your whole foot.
A Ride Through 250 Years
Montauk was pasture long before it was a beach town. In 1661 East Hampton livestock owners bought grazing rights to the Montauk grasslands from the Montauketts, and by 1687 they held title to the grasslands outright. Every spring they drove cattle, sheep, and horses east, and paid keepers to live out there in three houses spread across the hills and watch over them.
During the Revolution, the grazing lands held roughly 2,000 cattle and 4,000 sheep while British warships operated offshore. The region’s livestock and supplies made Montauk strategically important.
Third House | Montauk
For many, horseback riding is a passion that transcends generations, bringing families together.
The easternmost of the three keeper houses still stands in the same park the ranch rides out from, and it is a stop on the Suffolk County 250th Anniversary Historical Passport. You can collect a stamp a short walk from where you saddled up, though the visitor desk keeps limited seasonal hours, so check before you plan around it.
A century after the Revolution, these fields filled again when soldiers returning from the Spanish-American War were quarantined at Camp Wikoff. Theodore Roosevelt and the Rough Riders turned their horses out on the same pasture, and the park now carries his name.
Riding Lessons
A guided trail ride is the easiest way to experience Montauk on horseback. Visitors who want more hands-on instruction can also book lessons at East End barns in Amagansett, East Hampton, and Riverhead. Availability, rider ages, lesson formats, and requirements vary by barn, so contact each stable directly before making the drive.
As you ride, you’ll encounter diverse wildlife, making horseback riding a perfect way to connect with nature.
For those who love adventure, horseback riding on the beaches of Montauk is an unforgettable experience.
Whether you’re searching for tranquility or excitement, horseback riding in Montauk can offer both.
Where to Learn
Amagansett – Stony Hill Stables is a recognized riding academy about a mile from the ocean, teaching from age four up through adults getting on a horse for the first time. Private, semi-private, and small group lessons, with a summer camp that has been running since 1976.
East Hampton – East End Stables is a smaller barn offering instruction and a pony camp starting at age three, which makes it the softer landing for families with young children.
Riverhead – North Fork Equestrian is a hunter-jumper facility on the North Fork, offering instruction for first-time riders through serious competitors on open farmland at the entrance to the fork.
Local Tip
Book before you drive out. These are working lesson barns rather than walk-in operations, and summer weeks fill early.
Make a Day of It or an Overnight
In conclusion, horseback riding is not merely a leisure activity; it’s a way to create memories that last a lifetime.
The earliest rides are the ones worth planning around, which is an argument for waking up out here rather than driving in.
Montauk in Summer
Ride early while the trail is still cool and the light is low across the field, have lunch in the village, then give the afternoon to the beach. Stay the night and you are back out on the water or the sand before the busiest part of the day.
Montauk in the Off-Season
Rides run year round, weather permitting, and the fall and winter trail feels markedly different: quieter, wind-scoured, and far less crowded. Pair a morning ride with a walk out to Montauk Point, where the park stays open year round even after the lighthouse museum closes for the season, and stay overnight when rates tend to run below their summer peak.
Make It an Overnight
Montauk offers a range of places to stay within a short drive of the ranch. Explore where to stay across the East End →
Before You Go
- Beach rides are for riders age 8 and older. Trail rides start at age 6. Pony rides are available for younger children.
- The ranch lists a weight limit of 240 pounds.
- Wear long pants and shoes that cover your whole foot.
- Reserve ahead. Ride schedules vary by season and the earliest times go first.
- Lesson barns are not walk-in operations. Call before you drive out.
See Montauk from the Saddle
A ride in Montauk offers a different perspective on a place many visitors experience from the beach or the road. Between the open fields, the park trails, and the coastal air, it is an outing that feels distinctly local and a memorable way to spend time on the East End.
Want to cover the same ground on foot? Our guide to hiking the East End covers the trail networks at Theodore Roosevelt County Park, Hither Hills, and out to Montauk Point.
Find your East End.