I'll start with the fact that i created a Yelp account solely to spread the word about how amazing this place truly is. Me and my girlfriend are 25 years old and i was looking for a special place to celebrate our 6yr anniversary. She's always wanted to go horseback riding, so i went on google to look up places in Westchester NY to do so. I was surprising her with this, so i really wanted to make sure the place was perfect. So, i went to the only place that could help....Google. The first and closest place that came up was Wester Trail Rides. After the glowing reviews i saw, i decided to contact them for price and to set an appointment. In a few short hours i was contacted back by Cowboy Bob. After explaining why i wanted to do this via email we came to a day and time to come ride. What came after, when we arrived, was the best anniversary we ever had. THE REVIEW: Bob (the owner) had agreed to pick us up at the Croton train stop, which he offered without me having to ask. I was perfectly fine and had already planned on taking a cab. While it seems like a small courtesy, it went a long way for me. We got into his truck and began the drive. Bob is extremely easy going and all around the friendliest person. You can tell after a few minutes of talking, that he loves and has a passion for horses and has truly earned the name Cowboy Bob. After sharing stories we came to the ranch. It is quiet and beautifully green. (which is a nice change of pace from city life) He introduced us to his horses and gave us a little need to know info on horses. He let us walk right into the stable and pet them as well. I need to add, that even though our time was for an hour and a half, he never made us feel rushed. He made us feel so welcome, like we belonged. After the small teaching we met Dylan, i believe he is 17yrs old and Bobs son. This boy is the nicest and ill admit, coolest person I've met in a long time. You can tell right off the bat that he has been doing this is whole life and is a great teacher, as he was the one who got me and Jackie onto the horses and taught us how to maneuver. He is extremely easy to talk to and made everything real simple. After about 15 minutes of lessons, we were on the trail with Dylan leading the way. On our ride we got to chat and get to know each other but also enjoyed the peaceful silence of the woods. Every so often we would stop and Dylan would talk to us and answer all the questions we had. We had plenty.Its not often you meet a teenage cowboy. He showed us all kinds of cool spots and even taught us cowboy terminology us city folks don't know. (i.e Bushwhacking. spelling? lol) The whole time we were in awe of just how green everything was. It was even cooler on the trail because of all the tall trees. I thought it would be a generic trail around a ranch but to my delight, it really is IN THE WOODS. It added to the experience and ill admit, made me feel like a cowboy. I could have rode a whole week straight but eventually our hour and a half came to an end. Even when we got back, we talked some more and still didn't feel rushed off. Bob was even kind enough to give us an anniversary gift. Which wasn't necessary because we got way more than what we paid for. We took pictures with Bob and Dylan and were taken to the train by Bob. We waited for our train in shock of how perfect everything was and how awesome our guide Dylan was. In closing, it was truly the best anniversary in our 6yrs of being together. It didn't feel like an activity we paid for, but more like a good time with friends. If horseback riding is something you are doing for the first time, like us, or you go often, do yourself a favor and GO HERE! Thank you Cowboy Bob and Dylan for making this day special. You will definitely see us agin before the summer is over. -Sincerely, Jackie & Shayne read more

It's clear that this business is a labor of love for Cowboy Bob. My brother was in town for the NYC Marathon, and I thought it would be a nice memory for the kids to have their uncle bring them to ride real horses. Boy, am I glad we came. This was way better than the typical pony-led-around-a-circle like you get at other places! After scheduling a late afternoon ride via text (the weather was iffy, and Bob and I were in constant contact the day of to make sure we could proceed), we arrived at his home. At first, I thought we might be lost because there aren't any big signs that announce the location, but there was a small one that said visitor parking. (It makes sense that there isn't more signage, because it IS his home, and he has neighbors.) The first thing the kids did (3 and 8-years-old) was play with the two miniature goats. That got them in the mindset of being around animals. I think the whole experience was brilliantly choreographed, where the kids got to phase into riding the horses. Cowboy Bob explained some safety stuff about horses that the kids could understand, and then he introduced us to the horses. He let my 8-year-old lead her horse around the paddock for a bit before saddling everyone up and letting us ride them around the paddock. My little guy was too small to ride a horse by himself, so he got to ride with his uncle. After everyone was used to the horses, we got to go on the trails. The horses were very gentle and well-trained, so basically all we had to do was not let them take us through low-hanging branches. The foliage was beautiful, and Bob did a great job of pointing things out and telling us about the area. He also took some pictures and video for us! When we got back, he let the kids run around in the chicken coop and gather some eggs, and then he even found some old horseshoes to give to the kids. The whole experience felt more like bringing the kids to visit the world's best grandpa than a business transaction. It was a wonderful memory, and my kids have been talking about it non-stop since. He mentioned that they even do rides in the winter when it snows, and I think we will be back soon! read more

Cowboy Bob has a beautiful farm/ranch with chickens, billy goats and horses. My husband and I went on a 1.5 hour trail ride and from start to finish Bob made it an amazing adventure. I believe you have the option of both Western riding and English riding. The horses know how to take both direction. We did Western. Helmets and water provided. When we arrived he introduced us to his newly added billy goats who were so sweet and wanted to play. You can hold them and pet them and they snuggle right up to you. The horses were already saddled up and after a quick demo and walk in the corral we were on the trails. He told us about the surrounding area as we walked through the picturesque wooded trails. As we became more comfortable we requested to go to an area where we could cantor a bit. He was very accommodating and took us around the reservoir (also beautiful) and we had an opportunity to really feel like cowboys. Please note - I'm not sure if Bob does this with everyone as we both had experience riding. These horses are powerful and fast so don't be discouraged if he says that you may not be old enough or experienced enough. I'm guessing its a case by case basis. Even with experience, these horses were fast so it could be scary for some. You can tell Bob loves the outdoors and loves being a cowboy which makes the experience that much more fun as we learned he used to be a competitive bull rider. He made us feel like our experience was priority #1 as he was very attentive and made sure we had a good time. I highly recommend Bob and Westchester Trail Rides. I plan to bring my niece and nephew for a ride around corral and to play with the billy goats in the coming weeks. Bob loves visitors and so do his animals. Thank you for a great adventure Bob! read more

We went for a fall trail ride this weekend. My 9 year old son was having none of it, didn't want to go, was TERRIFIED of even sitting on a horse, even for 5 seconds. How scared? He was even scared of the barn cat. Cowboy Bob exuded kindness, warmth, compassion, patience and SAFETY. He isn't just a horse whisperer, he is a kid whisperer. First he got my son to just sit on the horse, He begged to come off but he said let's just sit there for a while. Then he asked my son if he would let the horse take one step. He said ok, only one. Then a minute later two steps, Then 3. Then he walked around the corral with Bob leading the horse and me holding my son's hand. Then I walked him around. Would you believe. 15 minutes later this kid who didn't even want to be near a barn was on a trail ride tethered to Cowboy Bob and doing just fine and when the ride was over he was all, "That's it? That was GREAT!" Long way of saying - this is a great business with an interesting, compassionate owner who is serious about safety, equine care and taking care of guests. And the price was reasonable too. We will be back. I can't recommend this business enough, it was really a spectacular experience, Bob works hard for and deserves every success that comes his way. And here is the bonus (and proof he is a kid whisperer): He told my son to make his bed because cowboys always make their beds. Now, my son has no desire to be a cowboy AT ALL but this morning he's up at crack of dawn making his bed. Cowboy Bob is a great guy, you won't regret a day spent on his farm with Apache, Gabby, Chocolate and the other beautiful horses. read more

I went with two of my friends and I can speak for all us when I say we had an absolutely wonderful experience!! As soon as we arrived we received a very warm and friendly welcome; it was a pleasure just being there and talking to Cowboy Bob. It was my first time on a horse, but Bob put me at ease immediately. He gave us the instruction we needed in a way that made us feel capable, but not overwhelmed. It is obvious that he has an in depth knowledge of horses and riding, so we knew we were learning from the best and that gave us the confidence we needed to get the most out of the experience. We started with a quick walk in the corral which I really appreciated because it helped us to get accustomed to the horses before going on the trail. The actual riding was excellent. Bob was continually providing us with the 'technical' support we needed as well as telling us the most interesting facts/stories about the area. We learned so much as we went along and the scenery and atmosphere were perfect. In fact I had such a memorable experience that I've since gone back twice, once by myself and then with my daughter. I highly recommend Westchester Trail Rides- you will definitely not be disappointed and may even become addicted to riding as I now am!! read more

I highly recommend Westchester Trail Rides for an uplifting and memorable ride! My only other experience riding a horse was a frightening one during a beach vacation with an untrained horse and an indifferent guide. My husband loves horses, so I planned this for us after reading other great reviews, hoping a good experience would help me get over my fear. Within minutes of meeting Bob, the owner and our guide, I felt comfortable. He gave me a mini-lesson and spent time introducing us to the horses. The trails went deep into the woods under a canopy of trees and down to a stream. It was hard to believe we were just in Westchester County! We stopped at points along the way to admire the beauty of the land and Bob offered to snap a couple of photos of us with my phone, which just shows what a considerate guide he is. By the end of the lesson, I felt confident and inspired by the entire experience. On top of all of this, I also got to pet the goats and Bob gave us some fresh eggs. My husband and I plan to return in the fall. This is cash only so remember that on the day you come. Westchester Trail Rides is very affordable and well worth every penny! read more

BOB IS AWESOME! WESTCHESTER TRAIL RIDES ROCKS! I went for a ride with my husband,uncle,and his wife.It was AMAZING.Bob was so patient and took so much time to explain everything to us and to make my aunt (who had never ridden before and was extremely nervous) feel so comfortable.His personality is so warm and inviting.When we were done riding the breathtaking trail through the mountains and returned to the pen,he went inside and the next thing we heard was Bob Marley blaring from the speakers!It made the experience so much more personable because we are Jamaican.We left there feeling like we knew Bob for years.My aunt was so comfortable and fell in love with her baby Dakota and even planned to come back in the fall again to ride him again.I made an appt to go right back the following weekend with my in-laws.Bob is a wonderful human being and we pray much blessings on him and his family.We deemed Bob an honorary Jamaican and he is now "White Bob Marley";)..IRIE BOB!! read more

Today my boyfriend and I went on a hour trail ride with Bob that we both won't forget it! Very easy to find with the help with Bob's directions. Once you pull in you see the beautiful red barn. The barn had this amazing comfy feeling to it with country music playing with a western vibe. We mounted up and he let us warm up in his ring, which was so nice to get the feel of the horses before we headed out. After that we headed out to the trails which are stunning and so peaceful. Throughout the ride he would stop and tell us about the trails and what's around. He let us concur the hilly mountains on our own pace which made us feel so comfortable and safe. After the ride he gladly let us help around the barn and give our horses some well deserved treats! He also let us grab some fresh eggs out of the chicken coop ! The best place to go for a trail ride in Westchester! We both will be back in the future, there's no doubt about it ! read more

What an amazing way to spend a Sunday morning! My fiancé surprised me with this experience for my birthday today. Neither one of us had ever ridden a horse before and didn't know what to expect. Cowboy Bob was friendly, funny, welcoming and thorough! He introduced us to the horses and explained how to understand when the horse may be feeling nervous, calm, or mad. He gave us a safety lesson and modeled everything from tightening the saddle and appropriately mounting the horse to a brief history lesson on why everything starts on the left side. He let us practice riding in the gated area until we felt comfortable and then took us out on the trail. He really gave us personal and focused attention. Nothing was rushed. It was an amazing experience and we will be going back 100% Highly recommend this experience with Cowboy Bob!!!!!!! read more

It was our first time going to Westchester Trail Rides. I was looking to take my wife riding since she used to ride when she grew up. Me, on the other hand, had Zero experience. No problem for Cowboy Bob. He was great! He was very professional, knowledgeable, and was able to easily provide mixed level instruction to the both of us. The scenery on the trail is beautiful. The horses were all very well trained and properly taken care of. Insider tip; try to come a few mins early before your session, as the property has a few other animals (other than horses). We arrived a bit early (due to good traffic) and were greeted by friendly/playful goats and a cat. The entire experience offered a very relaxed / not rushed atmosphere and wonderful experience. Will be going back for more! read more

My family and I had an absolute amazing time all The animals are well taken care of and loved! Which was huge for us because we are animal lovers.. We only went for the 1 hour ride because it was our 1st time But I must say it was such an awesome experience Lauren the Barn Manger was a sweetheart and such a pleasant welcoming person, Ruben our trail guide master gave us some cool knowledge of all The horses, their personalities and the history of each horse we we're riding which was cool.. He was funny too which made the experience even better he gave us a quick lesson and all the do's and Don'ts Ruben is a real super cool dude We look forward to becoming regulars and doing the 2 hour ride in the snow this winter... We found our Horse riding home thanks guys you rock read more

Much like what so many others described here, my family and I had an incredible experience with Cowboy Bob!! Our 9-year old was verge-of-crying scared at first, but with endless patience and empathy, Cowboy Bob made sure he acclimated her at her pace to being on the horse (Apache) and then riding him. With his guidance and Apache's intuition, her fear dissipated with each passing minute. Soon, she and the rest of us started thinking about when we could return. The ride through beautiful trails, along with other fun treats throughout the day (playing with baby goats and farm-fresh eggs), topped by my daughter proclaiming as we left that she feels like now she could accomplish other difficult things made the whole visit worth every penny! We'll definitely be back. :) read more

Since I previously had a ranch, and showed Cutting Horses, I was excited to find a place in NY where my boyfriend and I could go for a trail ride. Bob was the ultimate host, beautiful barn, and horses in the best condition. Bob took the time to give my boyfriend a short lesson on Apache, and explained "horsey psychology". He is a very patient and kind teacher. We went out on the beautiful trails, akin to Walden's Pond, and had an amazing and beautiful morning. His horses are very well behaved, and even a novice rider like my boyfriend felt very much at ease. Bob is the absolute best, and we will return come winter to have a ride in the snow. Now that is an amazing experience! I highly recommend Westchester Riding Trails. Take it from someone who knows horses! read more

Riding with Cowboy Bob and Dylan is a wonderful adventure! Their ranch and animals (from horses, to chickens, to goats and more) are gorgeous, and their trails are lush and exciting. We've ridden a few times with both Bob and Dylan, whose guidance has been illuminating for both the new and experienced riders in our party. I personally had never been on a horse and now feel totally confident trotting and cantering after just a few rides. Bob makes the whole experience personal, comfortable, and exciting. He has decades of experience riding and can deftly answer any question you may have. It is so evident the love he has for the horses and for sharing his knowledge of riding with others. Every time we finish a ride, we can't wait to come back! read more

My daughters and I had a great time with Lauren who was so patient and sweet with my 6- and 8-year olds. They had both ridden before in lessons but had never had the opportunity to take a trail ride. This was the perfect option! Lauren lead my six year old on foot and let my eight-year-old ride on her own for the first time. It was a very easy trail ride but absolutely beautiful. We even were able to walk the horses in a creek! Lauren was so patient with them as they struggled sometimes and the horses were so docile and sweet. After our hour-long trail ride she even spent some time with us in the barn so the kids could hold some baby chicks that had just come in. It was such a special day and we made some great memories! Highly recommend! read more

I done some research and I found Westchester Trail and I am so happy I found this place! I went further than I did and saw Ruben riding Chocolate and he directed me where to find the farmhouse. I arrived and it was like Cowboy Bob knew who I was. He let me brush them to get acquainted with the horses and I rode off with Cowgirl Lauren and the beautiful mare Gretchen. It was amazing hour & a half and she is great! When I was returning back I met with Ruben who is very nice! I love Chocolate and he is sassy and super sweet especially when he decided to cross the water. I am especially coming back as I am a true Cowgirl at heart and to gain more experience. Being surrounded by these majestic beautiful creatures made me feel whole! read more

Fantastic afternoon at Westchester Trail Rides! Bob was extremely responsive and thorough via email, patient with our questions and schedule changes. The rides depart from Bob's home and ranch, at the end of a beautiful winding road only 10 minutes off Route 9A. The idyllic farm has 6 horses, 2 very friendly miniature goats, a many noisy chickens, which kept us entertained both before and after the ride. Within minutes of arrival, we were out on the wooded trails behind the house, riding for an hour, taking in the scenery, and hearing about the history of the trails and the horses from Bob. Once we returned, Bob's son Dylan hung out with us while we got more goat time. A fantastic way to spend a few hours in Putnam County! read more

Jasmin and I had a wonderful experience with Westchester Trail Rides. This was my first time ever riding a horse and both Cowboy Bob and Dylan put me at complete ease in getting started. Dylan was our teacher, guide, and trailmaster and did a excellent job in making us comfortable and leading us on a beautiful and scenic trail ride. I had the joy of being able to ride Apache Retreat who possessed a great sense of where I was at as far as confidence and ability. Apache Retreat allowed us to canter a few times which was thrilling and definitely not something I envisioned happening the first time out. Dylan was extremely gracious and helpful during our ride and we could not have been more pleased with our journey. read more

What a great time with Cowboy Bob and the gang. A group of 5 of us went for a trail ride and had a wonderful time with Bob and Dylan. We started out by meeting some baby goats and chickens around the farm which put everyone in a great mood. Bob and Dylan introduced us to the horses, and allowed each of us to get used to riding inside the pen before setting off on the trails. We took a great hour long ride through the trails behind the farm with beautiful scenery. They were very accommodating, and were willing to take pictures of our groups along the way, and even sent us off with a dozen fresh eggs on our way out. Whether you're a first timer, or a cowboy at heart, this spot is definitely worth a visit! read more