The Ranch

Great ride! Horses were all very well behaved, Austin did a good job checking on everyone throughout the ride, and it goes without saying that it's a beautiful ride through the state park and onto the beach!

Can't say enough good things about this place!! I came out here with a group of 10 for a bachelorette party in October and we had an amazing experience! Cate, the owner was an absolute delight to work with and she was so helpful. I probably called 10 different times with numerous questions/changing the group size, etc. and she was so patient and accommodating. They provide the helmets and any additional equipment needed for the horse back ride. Our group was a divide of some experienced riders and some total beginner's, some of which were very nervous and afraid (myself included) and they were really good about helping us feel comfortable. There was a guide at the beginning and the end of the group. The ride was pretty long, about an hour and a half and we went onto the beach for part of it which was really pretty. We also did some advanced riding, called trotting, which was a bit scary, as a non-horse lover, but it ended up being fun! This is definitely a fun and different activity. I will warn that it is pricey though at 180$/person!

We enjoyed our beautiful horses and picturesque trail ride down to the beach. Our guide was on her phone at least half of the one and half hour tour and could have been more helpful with a guest who was riding for the first time and pretty much list behind the group the entire time. Overall, the rest of the staff was friendly, and we enjoyed the ride

Proclaimed oldest ranch in the country, lots of fun this morning. This land is full of a rich history including Teddy Roosevelt, Mickey Drexler (former CEO of J.Crew), and concerts by Paul Simon, Jimmy Buffett and Billy Joel. Currently run by (concessionaires) a local Montauk woman Cate and a legendary Coloradan cowboy Pat. We did the 90 minute ride accompanied by Skyler and it was exactly what we needed. A warm welcome, safety first mentality (for riders and horses), and a hop onto beautiful trails throughout some 30 acres of land (did I hear that correctly?). Horses were very rideable for a first timer, and for my son who thinks he's Wyatt Earp after four weeks of riding horses at camp. Prices seemed fair compared to much more expensive nonsense you can blow your money on out here. Don't forget to tip your guides, they have a passion for what they do and keep you safe. The views are nothing short of life changing. Enjoy!

DANGEROUS! RUN away from this horror filthy place. My husband almost died. Austin is 15 years old and was the ONLY guide on the trail. They had NO water at all. The 15 years old panicked when my husband was so dehydrated and had to get off the horse because he nearly fainted. I had to beg Austin to help my husband and call for help. This ranch is NOT prepared for emergencies and I had to beg them to call the EMT to get medical help for my husband. The owner Patrick was furious i insisted on getting emergency help for my husband. They have NO water available on hand for guests. This is a DANGEROUS facility. DO NOT come here. They should be reported for their failure to provide safety and having a panicked 15 year old as the only guide on a 1 and 1/2 hour ride. It took 24 minutes for them to get my husband off the trail I'm attaching the picture of the 15 year ome. This place is a death trap. Run away from this hell hole

Visited here in late July with family. The staff were friendly and the horses and ranch were clean. My son was able to ride for 30mins which was perfect for him. Rest of the family had a 1.5 hr ride to the beach and back.

Great local stable for short rides. Very nice and professional staff and owner. Had a great time. Had no idea they were out there until we drove past on our way to the lighthouse ..

I am not recommending this stable because the owner has so much attitude and was not accommodating at all. We wanted to know why we were unable to ride on the beach so they called her and she came down and the first thing she said was " Is there a problem" She had so much attitude. Also we had to pay in cash and they required us to pay a $30 per rider gratuity paid in advance in cash as well..? Who does that? It was also extremely pricey.

TERRIBLE EXPERIENCE!!! They charged us 300$ for the trotting instead they just made us do the walking. STAY AWAY FROM THIS PLACE. They had missed communicated the other family about the package and we got stuck with just walking because one of their group members got scared of trotting. No apologies at all, all she said it's nothing we can do. They only take cash UPFRONT so it's nothing you can really do. Do yourself a favor and don't waste time with this activity since there is no guarantee that you will experience what you paid for!

This did not disappoint. we had a wonderful time riding to and along the beach. From the moment we arrived the staff was friendly, helpful and informative. our trail guide, Gabrielle was experienced and knowledgeable. The horses were beautiful. The weather was perfect and the other riders were fun. Overall this was a very enjoyable experience. I highly recommend it.

I FELL IN LOVE WITH THIS PLACE! Gosh, it was such a perfect activity to do while being in the Hamptons. The staff was friendly, and very helpful and made the experience really enjoyable for us. However, it was advertised that the ride was going to be along the beach, so we thought we would get to do that, but it was actually through the woods, nonetheless it was a great experience, just wish we knew it wasn't going to be a beach ride.

Awesome experience a few years ago here. Our instructor even offered to take pictures of us the whole time. Can't wait to go back!

It was my first time going to horseback riding in Montauk. I was very lucky to get an appointment a day before. I loved walking on the beach. I went for 90 minutes riding but not enough! This is a very good activity for everyone if you come to Montauk. Truly recommend. You can't bring big camera on the horse but you are fine using your phone if you would like to record your memory. I thought their receptions need to communicate better. I was 10 minutes late so called them beforehand to let them know I'm going to be 10 minutes late. The person I talked told me that that's not going to be a problem. Then different person called me about I'm being late and if I still want to go. It's so annoying that I have to explain the same thing I already talked. It's reception's job to keep all the information organized.

If I could give this place 0 stars, I would. The owner, Cate was extremely rude and unprofessional. I was in an unfortunate situation where I needed to shift the dates to a couple weeks after my gift certificate expired and I just asked for a short extension and the response I received from the owner Cate was "our prices are different now, you had a year to use it." And then she said I have customers waiting for me and hung up. I then wrote an email, and Cate's response was "I too have missed gift certificates due to time and respected the policy of the business. There are no exceptions." The most disappointing thing was that my gift card was for $500 and she wasn't even willing to make an extension for an extra 1-3 weeks. I wasn't asking for my money back all I wanted to do was get an extension. I wouldn't want to do business with an owner who doesn't prioritize their customers needs.

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.

Beach ride? I think not. If you're up for just being around horses and the feeling of being in the saddle for awhile, this will accomplish that. If you're thinking this will actually be a beach ride as advertised, walking (erase the thought of galloping) along the beautiful Montauk shoreline with waves lapping at your horse's hooves, or leaving hoof prints in the sand, it's not that. If you're thinking you'll ride along the beach for even 10 minutes of the 90 minute ride, it's not that either. If you're thinking you'll have a long slow walk for 40 minutes, on a not-scenic trail, in a caravan with up to 9 other bored horses trying to grab whatever they can eat along the way, with a 5 minute walk around a tidal pool (you won't go anywhere near the shoreline), and then another slow walk down the same exact not-scenic trail for the 40 minutes back to the barn, you're right. Staff is pleasant enough, horses look taken care of enough. My saddle flap broke off along the way - - indicative of old tack that's not well-checked. But to call this a "Beach Ride" - in any way - is taking advantage of technical language because, technically, we did traverse sand and a little tiny bit of water, but it would never be what anyone would think of as a "Beach Ride" or even a partial beach ride. If you think $110 plus very (I repeat, Very) high-pressured-gratuity is worth it for walking a horse from Point A to Point B and back again, with a little hint of sand just to legitimize false advertising, then you'll love it.

this gorgeous place, people and horses deserve 5 stars!!!! The horses are sweet and gentle and while they may stop at times for a little grass, come on, who doesn't! They were so sweet and our leader Kate was a real gem. She made me and girls feel at ease and was watching out for us and her horses the entire time. It was a real pleasure and divine joy! Really can't say enough good things! Just go people!

Olga our tour guide was very rude. She made it an awful experience for us. If you have an option to choose your tour guide pick some one different. She was very snippy with the children and us in the group. If you have children definitely don't use her as a tour guide. They do not guarantee a photo of the experience. You pay all that money and you may walk away with no photo of the expierence. A different tour guide took great photos of them on the beach. Our tour guide Olga did not. Because of my expierence I would not go again or recommend.

The staff at Deep Hollow were just great. We had a cold raining day today and had to cancel our reservation. Deep Hollow gave us options on different times if we'd like and completely understood that we wanted to come back on another day when the weather was a little better. Great communication!

My daughter and I went on the trail/beach ride. We had a great time. The staff were great. The horses were easy to ride. They seem to know the trail very well. Our guide carvel was great took pictures of us on the beach, with our camera.. thank you

Beautiful ranch, Staff is really pleasant , horses seem healthy and happy, my young daughters 6-4 had a great time.... 6 year old was able to ride by herself on 30min trail ride... it's a walking trail so she was very comfortable her horse Sammy kept good pace no galloping and was well tempered...my 4 year old was too young so she rode the pony named LIL Horse.... will be back for sure...

Women who gave us two second instructions in the beginning was so unbelievably rude and mean I will not be coming back here again she ruined my entire experience with her attitude extremely unprofessional

Lovely place for a ride. We called and were able to get a reservation the same day. Went for a half hour ride, 2 adults and 2 kids with our guide. It was so peaceful, and a lovely trail through the woods with some nice views. Perfect activity for a fall day. The receptionist and trail guide were both very friendly and the horses were beautiful.

My bff and I had a great time. We still laugh about it. The guide was very patient as we were a little stiff and having second thoughts since the beginning. No regrets! Greetings to Bob and Billy!

The owner is extremely Rude, unprofessional, unpleasant. No instruction, no kindness, no flexibility. Only her money. The actual ride on the beach last 5 minutes. I don't suggest anybody to ever visit this place. By the way , they only accept cash! Wonder why!!!

Something different to do during your next visit to Montauk. Cool little horse ranch where you can ride on the scenic hilly trails and even down to the beach (90 minute) ride only. The horses seemed tame and calm and the staff are friendly and helpful. It's pricy, $45 for 30 minutes, $75 for an hour and $85 for the 90 minute ride which takes you to the water. Want to just take the kids for a quick pony ride, $10 only. Tours run every other hour. Again, something different and worth the visit.

Great tour and amazing guide, Skylar.

Had a great time riding at Deep Hollow. Our tour guide Olga was super friendly, knowledgeable and gave clear instructions. It was my first time riding and it went smoothly. I wish we stayed at the beach to take photos but overall such a great experience. Would come back!

As a horse owner, I found the horses to be filthy dirty and not groomed . The saddles and blankets were dirty and worn. The lady riding in front of me lost her stirrup. It just fell off ! No apology from staff. The ride was nice and horses were trained to just follow in a single line. I was not impressed. Horses were obviously fed and filled out but were old and seemed tired. Before the ride, there was no instructions on riding or handling of the horses. Would of been nice to give some basic information on riding technics.

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.

My girlfriend and I went horseback riding about three weeks ago for our anniversary. I meant to leave a review earlier. We had a great time. Kate, the owner took is for a private ride that I included going on the beach. She was great. We had a great time and I would highly recommend Deep Hollow.

A MUST in Montauk... the view and the beach ride were breath taking. Horses were trained really well and our guide Olga was friendly and informative. Def worth the money!

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!

My daughter and I went on the trail/beach ride during our recent stay in Montauk. Our guide Ellen was lovely, very attentive and informative. The ride itself was very nice, especially the beach which was beautiful. My only complaint was my horse, Raindance. In the wooded areas he would constantly go to the left as he didn't want to walk on the trail (Ellen thought his hooves might have been hurting). He would brush me up against thorny bushes so often that my leg got badly cut. No matter how many times I tried to pull him over to the right he would keep going back to the left. It was exhausting!

One of the best hidden gems on Long Island. We have to ride here as a family at least once a year! A truly wonderful experience and the views are spectacular.

If I could give this zero stars, I would. Complete rip off. The "beach" ride is basically a long ride through bushes, 2 seconds on the beach before turning back around and heading back through the woods. Way over priced! The girl running the trail ride was on her phone the entire time and didn't care to notice when one of the horses kicked back and nailed some guy on a different horse in the foot...luckily he was wearing boots, but they girl seemed like she was too busy texting to care to check if he was ok. Horribly unprofessional and definitely not safe (as you can read in other reviews on here and on trip advisor) COMPLETE WASTE OF TIME AND MONEY!

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!

This was my favorite thing that I did on our trip to montauk!! The scenic view of the beach was more then 5 stars most beautiful thing I've ever saw! The horses were tamed and listened well! We really enjoyed this ranch and will deff be back!!

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.

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.

Great horses, friendly trail guilds. Best beach to ride on. This isnt running on the beach crazy. A little Trott is more than enough. The ride is 1 1/2 hours. You may think you want more, but you will get quite the workout, without scaring the younger riders. Everything in Montauk isn't cheap. This stable, in my opinion, has the nicest beach. It has the least amount of rocks, and it is the most scenic.

Awesome place for anyone of any skill level. Instructors are super nice horses are very well taken care of and happy. You can't beat $85 for an hour and a half on the beach in montauk.

We took the 90 minute beach trail ride today and, given that we were actually on the beach for approximately 10 minutes, walked away feeling a bit ripped off. It took forever to get from the ranch to the beach due to the fact that half of our group were Japanese tourists who screamed in terror every time the horses trotted and one of whom wore open backed white leather mule shoes. Would recommend that the ranch require participants to wear the proper shoes, put two guides on rides, and also advise that part of the beach trail ride is trotting if you actually want time on the beach.

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 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.

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.

DEAR FUTURE DEEP HOLLOW RIDERS: THIS WILL BE THE WORST EXPERIENCE WE COULD POSSIBLY EVER HAVE HAD. Ive ridden at deep hollow in the past and it wasnt always my favorite. The tour guides are very strict and dont give you the experience you want. Today, 2 friends and i had a trail ride at 5 and showed up at 4:57. The lady at the front desk said we werent allowed to go and they had already given our spot away because we werent there a quarter before 5. They had never told us we had to be there a waurter before 5. Instead of even saying it nicely, they said it very rudley with bad presentation putting the blame on us for being "late" and didnt even say sorry. Heres where it all goes down. She says "its not my responsibility to get you here on time". Then we didnt even get our money back. WE STILL HAD TO PAY FOR THE RIDE WE WERENT ALLOWED TO GO ON!! $360 for 3 people! I highly don't recommend deep hollow. It is just a waste of money or you are paying for a bad experience. I would reccomend ritas stables, it is such a better and happier place.

I took my little brother to Deep Hollow Ranch almost 15 years ago when he was 12 years old and went back this week with him and my 6 year old daughter. When I called the day before, they were very clear that we could only take a 6 year old on a 1/2 hr trail ride and that it did not go down to the beach. Good thing too because my daughter balked at getting on the horse and I was sure we were going to be heading back without a ride at all. The staff there was amazing! They were patient and calm and once we got her on the horse, Kelly took her off on a little stroll while we all got up on our horses and by time we were all ready to go, my daughter was ready too! Our guide was so sweet (I'm sorry, I believe her name was Beth) and answered all 101 of my kid's questions while encouraging her and making sure she was comfortable. Thank you so much to all the staff. The trail ride was easy and slow and my daughter Esme has been talking nonstop about Dollar, the horse she rode. We will be heading back soon!