Deep Hollow Ranch, Montauk

3.9
Montauk County Park, formerly known as Theodore Roosevelt County Park, is located approximately 3mi east of Montauk, New York. The park is 1157acres in size, running from Montauk Highway north to Block Island Sound and is bordered on the east by Montauk Point State Park.
Montauk County Park was created from 1971 to 1986 through a series of land acquisitions by Suffolk County with the help of Hilda Lindley and the Concerned Citizens of Montauk. It was named for Theodore Roosevelt in 1998 to commemorate the centennial anniversary of his return to Long Island following the Spanish–American War, however it was re-named "Montauk County Park" in 2014 after concerns were raised about the insignificance of Roosevelt's actual involvement with the area.
The park includes: Big Reed Pond – a National Natural Landmark. Montaukett Village – a home and burial ground of the Montaukett tribe of Native Americans, which includes the grave of member Stephen Talkhouse Deep Hollow Ranch – the first cattle ranch in the United States, established in 1658 Third House – the third residence constructed in the 18th century for cattle keepers, who brought cattle to graze in Montauk each summer. The house is open seasonally. Camp Wikoff – where Theodore Roosevelt and his Rough Riders were temporarily quarantined after returning from the Spanish–American War in 1898
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Deep Hollow Ranch Reviews
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TripAdvisor Traveler Rating 4.0
69 reviews
Google
4.2
TripAdvisor
  • We were in the Hamptons for a week. Our daughter is horse crazy, so we arranged a surprise trail ride for her. We were met by the gorgeous Ashley who told us some of the fascinating history while Anya...  more »
  • Our family began riding here and we have great affection for it. Now they are good riders and really have outgrown it but we still have sentimental attachment. Guides are capable and friendly. Staff i...  more »
Google
  • Fantastic experience! Both for novice and experienced riders. The staff was super helpful and friendly. The horses looked as healthy and happy as could be. They were all very well trained and safe for all levels of riding. The beauty of that part of Montauk is breathtaking. I was mainly happy about how well the horses were taken care of. Couldn’t have been better!
  • We had the best time! Have to address some of the one star comments about grooming and care. I grew up with horses and have family with cattle ranches. These horses are at pasture, They love rolling in mud and dirt like happy horses do. I had a show horse that I would scrub and brush until her coat shined... and as soon as she got the chance, she'd roll in the mud! It's what they do :)... This experience was amazing. Kids said "the best thing ever!!!" Totally worth the price. 1.5 hours of real trail riding through beautiful scenes. The beach is the highlight of the trip, but the whole ride is beautiful and memorable. Our guide was funny, and chatted with us in a friendly, relaxed way. Our 9 year old had trouble keeping his horse from trying to graze, so our guide just put his horse on a lead rope, and he followed along behind her. As for getting pictures, we just took pictures of one another, so I ended up with lots of great shots. I'm sure if you ask for a shot, you could probably get something, but you don't actually stop on the beach, so the whole process is sort of "in motion." Can't wait to do it again!

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