Deep Hollow Ranch Beach & Trail Rides

My boyfriend suprised me with a sunset trail ride excursion on Sunday. I had been to the ranch years ago as a child and had a very positive experience. This experience was quite different.
My boyfriend had never been on a horse and though I have ridden for many years there was no real instruction, information about the horses we were on, or any safety tips. «This is Prince, hold the rein with one hand, pull up to stop, left and right to navigate, and don’t let him eat the grass.» What we found out was both our horses liked to stop and eat, mine backed up if you pulled it’s head from the grass, and my boyfriends horse would just flat out stop and not move despite the trail guide yelling back to kick with no results.
We were riding about 15 minutes and having issues with a few horses along the way– not wanting to follow other horses, eating grass, and the guide didn’t see but one of the kids in our group kept stopping and yanking his horse back then having it trot forward to make his siblings laugh. It made us nervous in the back but we only had one guide with us so he was never caught/​reprimanded for this.
Along the trail we got to a narrow part and the little boy who was riding behind the guide was having issues with his horse (like he was at other points on the ride) and he couldn’t get the horse to move. When the guide turns around on her horse, his horse backs up and falls down into a ditch and gets stuck with the little boy on his back. The guide jumps off her horse and grabs the horse that fell to keep the horse still and tells the boy to get off if he can, is he alright and once he was safely off in the bushes to get away from the horse. She then spends the next 5 minutes trying to get the horse free, radioing for help, and trying to pull the horse out. There was no instruction for the rest of up who’s horses started getting antsy with this other horse down in a ditch who was stressed. While this was going on the confused and frightened boy is trying to stand near his mother who is on a horse and getting yelled at by the guide to stand in the bushes. Another group was luckily in the area and another trail guide came down to help try to free the horse. Again, there is a group of us in a line on a precarious path with no instruction and just watching this scene unfold. Finally guide #2 tells us to keep our horses to the right and that a 13 year old boy who worked at the barn was going to lead our group and her group back to the ranch and to let them pass us on the right. All we see is a horse at the bottom of the trail and now about 5 horses with little kids coming at us on a narrow pass. Horses were bumping into each other, kids were yelling and scared seeing a horse in a ditch and it was chaos. My boyfriends horse was already turned around so I turned mine and when the guide passed we decided it was safest to not wait for a herd of horses to pass and go right behind him. We were not going to be in a stampede of 10 horses bumping into each other on a narrow path.
We followed the boy back to the barn who had never done this before and at one point one of the kids in the middle of our group was halfway off his horse and his horse started going into the field. The boy leading us just yelled at him to get back on the horse at which point I had had it. I jumped off my horse and lead my horse to the boy who fell off but luckily didn’t get injured and walked both horses with the group back to the barn. When we got back he told me to let the horses go I was walking and was helping kids off as there were loose horses walking all around us as one by one everyone got off. It was extremely dangerous with all the kids excited and worked up then to be running around a pen with 10 loose horses, some with their reins dragging on the ground. Eventually they got the horse out of the ditch which was totally fine and the boy walked back with the guide but the way the whole situation was handled was disturbing and extremely dangerous.
There was obviously no safety training in place, our guide completely ignored us and was more focused on the horse in the ditch then the little boy who was on the horse, the boy that guided us back did not have any experience nor a walkie talkie, and for the first time as a rider of over 15 years I felt scared on a horse. I understand «things happen» but the whole situation was handled poorly and very dangerously. I don’t care about a refund.
1. The staff there needs to be trained to handle all and any emergency situations.
2. There should be two guides for every group incase something does happens
3. They should have everyone walk, stop, and pull up the horse before just letting beginners handle an animal. It is careless to just have someone sign a waver and put them on a horse.
4. Rider safety over horse safety and not the other way around.

My fiancé and I did the 1.5 hour trail & beach ride at Hollow Creek. It was absolutely beautiful and peaceful. We loved every second of it. Sheldon was our guide, and he was extremely friendly. I mentioned I was a bit scared to ride and Sheldon chose a very gentle horse for me, and Joey was a great horse to ride! I cannot wait to visit again!

I called the day before to make a reservation for 4 of us. We got lost on our way there but we called and they provided instructions. After we got there, we signed the waiver and chose our helmets. Then we got on the horses and off we go! There was a couple that went with our group. It was a beautiful cloudless day and the trail was very nice. The beach is a little area where you can see the ocean 180 degrees and you make a U turn there to go back to the ranch. The horses are very clean and well maintained. The only thing was the trotting. IT HURTS! My thighs are still hurting after 2 days, but it’s partially my fault since I was not dressed appropriately for riding (shorts…). Highly recommend!

Great stable! Horses are all beautiful and well taken care of. Our guide was engaging and informative. Trails were beautiful! Highly recommend

I had such a great time on the trail and beach guided trail ride. We left around 10 AM and returned around 11:30. I went solo because my family isn’t the horseback riding type. Our tour was taken out by Eric, one of the managers at the ranch. He told us a lot about the ranch, the different scenery and was generally conversational which made the tour very enjoyable. Trotting was a little terrifying for me as a beginner, but with the tips the guide gave me I got more comfortable towards the end. It costs $ 85 per person but if you have a party of 5 or more I believe there is a slight discount. There are other options for trails and shorter times that you can inquire about! I’m happy I went, it’s been years and the beach trail was beautiful.

Die Deep Hollow Ranch in Montauk liegt direkt an einer Bundesstraße und ist sehr gut zu erreichen. Von Außen macht alles einen sauberen und ordentlichen Eindruck, die Pferde stehen entweder auf einer großen Weide oder gesattelt auf dem Paddock (was wir nicht umbedingt gut fanden).
Der Service und die Reservierung eines Trails mit Ritt über einen Strand, war ohne Probleme kurzfristig möglich, die Preise sind gehoben aber OK.
Die Guides bei den Ausritten und auf der Ranch waren freundlich, leider war alles so durchgetacktet, dass keine Zeit für eine Begrüßung des Pferdes blieb. Die Pferde wurden scheinbar nach einem Belastungssystem zugeteilt, Pferde die im Trail 2h vorher schon unterwegs waren hatten «Pause», allerdings gab es keine Anpassung der Pferde auf die Fähigkeiten der Reiter. Alle Pferde waren ruhig bis abgestumpft und so auch für Anfänger Problemlos zu reiten. Über die Verwendung eines «scharfen Gebisses» bei Anfängerausritten lässt sich streiten. Einen fortgeschrittenen Trail mit etwas mehr Tempo oder Freiheit gibt es nicht. Die Pferde trotten wie auf der Kirmes nur hintereinander her (nur mit deutlich mehr Natur).
Das wichtigste bei den Ausritten, die Natur:
Die Wege und die Landschaft waren wunderbar, am Strand ging es durch eine recht kleine Bucht. Der Ausblick entschädigt aber für fast alles!
Die Guides haben auf Tiere hingewiesen, aber sonst wenig über die Region erzählt.
Für Anfänger sicherlich eine tolle Sache, für fortgeschrittene Reiter etwas langweilig.
Eigentlich wäre es eine 3 Sterne Bewertung, der Stall macht optisch und Tierschutztechnisch aber einen deutlich besseren Eindruck als die lokale Konkurrenz, daher 4 Sterne.
(Disclaimer: Der Bericht schildert die Meinung meiner Freundin, einer sehr erfahrenen Reiterin)

The land was gorgeous but I think the trails should have been more open. Most of it was a straight line surrounded by trees. When we got to the beach it was amazing which made the ride worth it. The view was gorgeous. I do think the ride should be faster paced. The horses are practically on top of eachother in a line. I kept directing my horse to ease back a little because his face was on the butt of the horse in front of me. Of course they’re trained to follow eachother which I think is strange because I directed my horse to stop since 2 other riders fell behind. I wanted to wait so they could catch up but my horse would only follow the group. I don’t think the trainers need to tell people simple riding tips if the horses don’t follow them anyway, they’re trained to stay in line. It would’ve been nice to have a little more control but I understand that new riders wouldn’t like that. A woman in front me kept kicking her Horse and if he wasn’t trained to stay in line, the horse would’ve kicked her off so there’s pros n cons to that. I liked my horse he was spunky and took direction to a point. I might do a private ride next time. I would go back but I wouldn’t do a large group. But overall I had nice time.

Had a great time at Deep Hollow Ranch, Eric was our guide. He took his time with us explained everything. Best time of year to go is May and again in October less of a crowd. We basically had a private ride. It’s montauk everything is expensive what can you do but enjoy, but I still thought the prices were fair.

I’m going to have to go with «Meh. I’ve experience better.» on this one. Let’s go with Pro’s and Con’s shall we?
PRO’S
— Beautiful trails
— Amazing location
— Horses seem decently trained
— I liked that they actually had us trot a little bit. I’m restless if I go on a trail ride and you move a a glacial place the entire time.
— Probably great for kids — a little boring for adults with any experience.
CON’S
— Our group was 11 people including the 2 guides. It was definitely too large. Most high end ranch trail rides max out at 6. Also — I was told when I called that the groups maxed out at 8.
— Here were are on the oldest cattle ranch in the US and there’s no story line? No dialogue? Nothing learned? The guides should seem interested in the area and teach the people paying $ 85 per ride something about it. You could discuss — the Indian tribes that lived there, the history of the ranch, how you take care of the ranch today, how we take care of the horses, history of Montauk, geographical details? Anything? On our ride we heard this («there are two fossils on the ground there that we’re passing» and «look, we have some grapes back here — on the house!»
— Saddles weren’t comfortable and stirrups weren’t properly adjusted on several people.
— Wouldn’t have minded if even our relaxed pace was a little faster. I understand it’s a trail ride — but I’ve done about 100 of them and this one was SLOW.
— If your horses are only trained to walk in a single line — there is a problem there.
If you’re desperate for a trail ride — go ahead. But it’ll be a shame that they don’t improve upon what they’re doing today.

I had a great time here at good old deep hollow ranch. I had a special connection with one of the horses there. I’m not sure what it’s name was but I will always remember him. He was very friendly and playful. I highly recommend this ranch. So saddle up and go for a ride! Yee haw!

Not a place for children! I’d suggest going to Rita’s Stable instead. Their pony ride are $ 10 for 3 very short laps! When my little one didn’t want to get off we ended up spending $ 50 for 15 laps that was at best 10 mins long! We even asked if they would give us a better pricing option since he was «too small» to ride with an adult but «too big» for such a short pony ride, but they didn’t! Go figure, we were an easy target to make some easy money!

I brought the kids here for pony rides. They loved it. The horses were beautiful. However, the staff seemed disappointed that we were there. For $ 10 per pony ride, a pretend smile would have been appreciated. If you don’t mind feeling uninvited, this is the place to be. Next time I will give Rita’s a try.

From our first contact with the ranch to our last we were served in an excellent way. I thought that we were going to have a calm, slow trailride since we were all beginners and not to keen on looping or trotting. But our guide encouraged us to try all gaits in a nice way. It was a memorable moment for us! The horses were calm and sweet and the views along the trail and the beach is fantastic. Our guided pointed out deer and rabbits and was the best guide you can ask for. Great!

My girlfriend took me here as a surprise and will never forget what happened. The ride itself was so so, but don’t consider this a «beach» horseback ride. For an hour and a half you are on the beach for maybe 2mins. You literally walk around thorn bushes and once you get to the beach, you walk around the closest dune, circle back, and that’s it.
Furthermore, I was given a «new» horse who sprinted off at one of the forks and I did what I could to maneuver and stop the horse (I had pulled the reigns as far as the back of the saddle to no avail). The horse then whipped around a corner and I was thrown off the horse to what looked like an electric wire fence. Luckily they said the fence was turned off today…
I was bruised on my face, back, and butt, and my clothes were all torn up, but I managed to suck it up and get back on a different horse since I didn’t want to let this stop me from trying to make the most of this trip. Afterwards, I felt like the company would have maybe tried to offer some sort of compensation for the damages, personal and emotional, that had occurred. They didn’t even offer to give me a refund. I understand that we all sign waivers, but this comes down to good and bad customer service. As a business owner, you should look out for your customers regardless of paperwork or coverage. My advice-​spare your loved ones the chance that this might happen to them. They use their roses for rodeos and barrel races, so think about that before they have you sign the waiver. No one told me that!

I went horseback riding at Deep Hollow Ranch on Fourth of July. I chose to do the beginner trails because I haven’t been on a horse in quite a number of years. I thought the staff was extremely friendly including the girl who led our trail. My horse was beautiful and all the horses seemed content there. I recently went horseback riding in Costa Rica and the horses looked tired and worn down. The scenery was breathtaking, you don’t feel like you’re in NY. I highly recommend taking a trip to America’s oldest ranch!

Best trail ride of my life and I’ve gone on lots of them (Costa Rica, Nevada, Hawaii, etc.)
— The scenery is gorgeous. Really gives you a sense of what Montauk terrain is like. They even take you to a private beach with a stunning view. We also saw lots of deer along our ride.
— The horses seem very content and happy and cared for. And all of them on our ride seemed to be well-​behaved.
— I loved that they walked and trotted in a beginners group. They also have intermediate groups where you get to canter.

This is a great place to spend a few hours. They have beginner trail rides. that go through woods to the beach and back again. They wil help you pick out a horse that is right for you.
My mother changed her mind. when her horse started bucking! hehe. There was another huge black horse. a bit scary but I ok’d it for a kid. so on second thought. examine your horse closely. Really enjoyable place.