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Discover the Charm of Deep Hollow Ranch: A Horseback Riding Haven

Experience the legacy of horseback riding at Deep Hollow Ranch, the oldest working ranch in the U.S., set in the stunning landscapes of Montauk.

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Deep Hollow Ranch, located in the picturesque town of Montauk, New York, is a beloved destination for both locals and tourists seeking an authentic horseback riding experience. Established in 1740, it holds the title of the oldest working ranch in the United States, offering a unique blend of history and adventure. Visitors can enjoy guided trail rides through some of the most stunning landscapes in the region, with experienced guides leading the way through lush fields and along the stunning coastline. The ranch is perfect for riders of all skill levels, making it an ideal outing for families, couples, or solo adventurers looking to connect with nature. The ranch features a variety of horseback riding options, from short rides for beginners to longer excursions for seasoned riders. Each ride provides an opportunity to witness the local flora and fauna, as well as the breathtaking views that Montauk is renowned for. In addition to horseback riding, Deep Hollow Ranch offers a range of activities, including pony rides for young children, making it a family-friendly destination. Visitors can also enjoy the rustic charm of the ranch's facilities, which include a cozy gift shop and a welcoming atmosphere that embodies the spirit of the West. Whether you're looking to brush up on your riding skills or simply want to experience the tranquility of riding through nature, Deep Hollow Ranch promises a memorable adventure. As you ride along the scenic trails, take a moment to appreciate the serene beauty of Montauk, where the ocean meets the land, creating a breathtaking backdrop for your equestrian journey.

Local tips

  • Book your ride in advance, especially during peak tourist season to ensure availability.
  • Wear comfortable clothing and closed-toed shoes for a better riding experience.
  • Arrive early to explore the ranch and enjoy the scenic views before your ride.
  • Don't forget your camera; the landscapes offer incredible photo opportunities!
  • Check the weather forecast and dress appropriately, as coastal weather can change quickly.
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A brief summary to Deep Hollow Ranch

Getting There

  • Public Bus

    From the Montauk Train Station, take the Suffolk County Transit bus route S92 towards East Hampton. Stay on the bus until you reach the stop at Montauk Highway & Deep Hollow Road. This stop is closest to Deep Hollow Ranch. After getting off, walk east on Deep Hollow Road for about 0.2 miles until you reach the entrance of Deep Hollow Ranch at 1929 Montauk Hwy.

  • Bicycle

    If you're in the Montauk village area, rent a bicycle from one of the local shops. Head east on Main Street until it turns into East Lake Drive. Continue straight until you reach Montauk Highway. Turn left onto Montauk Highway and ride for about 1.5 miles. Deep Hollow Ranch will be on your right at 1929 Montauk Hwy. Look for the ranch entrance.

  • Walking

    If you're near the center of Montauk, walk east along Main Street until you reach Montauk Highway. Turn right onto Montauk Highway, and continue walking for about 1.5 miles. Deep Hollow Ranch will be on your right at 1929 Montauk Hwy. Make sure to watch for traffic as you walk along the highway.

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