This was really everything we wanted out of a trail ride. Bill took my phone as we entered the wooded trail & kept taking picture of us throughout the trip which awesome. The trail itself was fun. We went up and down some pretty steep inclines & thru a stream a couple of times. Way more interesting terrain than we city folk have ridden thru on past rides. This is just a one man operation so if you call & have to leave a message, understand that you are calling Bill's cell not some assistant, and he's either on a ride or getting the next group ready. It took a few missed connections for Bill & I to finally talk on the phone but it was worth it. Highly recommended for a fun laid back experience. read more

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Bill at the Rocking S Ranch was terrific! He was great at instructing what to do (we are novice riders) and an awesome story teller on the trail. We traversed different terrains and he documented the whole experience for us! We can't wait to come back again! read more

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We had an absolute blast with Bill at the Rocking S Ranch. Bill made sure each of us had the right horse depending on size and experience level. He was very funny and entertaining. You can clearly tell Bill loves what he does and it's not just about the money for him. It was a beautiful trail that went through streams and hills. Bill took my husband's phone so that he could take pictures and videos of us. It was a memorable day and we will definitely be back! Thanks Bill, it was great to meet you! read more

The Rocking S Ranch - Horseback Riding Near Me - Winchester, Virginia

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We will definitely go back! My husband, daughter and I went on a trail ride with Bill and had a wonderful time. It was relaxing, beautiful, and the perfect mix of laid-back but safety-focused. The horses were beautiful & gentle. I can't wait to go back. I'll have to remember to bring some dad-jokes with me to keep up with Bill! *Side note: I brought my phone with me, and thought I had it securely in my back pocket (duh on me) but I discovered when we got back that it fell out somewhere along the ride. Bill kept his eyes out for it on his next ride, and actually FOUND it!! WOW!! So grateful!! Also, take him up on his restaurant recommendations! read more

I lived in urban areas for most of my childhood - Los Angeles, Bangkok, etc - yet my dad always found places to take me horseback riding. There is possibly some underlying guilt because this extremely good little girl never got a pony for her birthday or Christmas. As an avid former Santa believer, I actually believed that I was not good enough for so many years!!! The love of horseback riding still remains with me to this day with dreams of one day having my very own horse. Yes Santa, I can be as "naughty" as I want and just buy things myself now!! I kid :-) It is this love for a good ride that took me to Rocking S Ranch. The brochure caught my eye as I was checking into a nearby hotel, the words "Open Year Round" thrilled me as not too many places are open during the winter times. Rocking S Ranch is awesome. A family run business who cares about their horses as well as your experience riding them. The owner knew his horses well and took care to match you to the right horse taking size and temperament into consideration. The trail we were on was beautiful. It took us up hillsides, through the woods, crossing streams. The guide/owner even took our cameras so we had digital evidence of all this. I mean he went camera crazy. I have to be honest; getting a picture of me on a horse crossing a stream was pretty awesome. TIPS: - Make sure you are in no rush that day. The reserved start time as well as the length of time of your ride is more of a suggestion. There's absolutely no rush to get started on time or get back on time. This adds to the relaxing atmosphere that I loved and I got more than what I paid for (which I loved more ;-) - $40 per hour, available from 60 minutes to 90 minutes to I think up to 4 hours. If you are new to the horseback riding thing, I would start with less. Don't want you to be stuck in some sort painful cowboy stance now :-) - Cash or check only. - Lastly be prepared for some pretty dorky but endearing jokes. read more

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Excellent ride including steep inclines and water crossings. Great views. Gentle horses and experienced guide. Fun for all ages, will definitely do gain! read more

The Rocking S Ranch - Horseback Riding Near Me - Winchester, Virginia

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Very rude person run this outfit, we decided not to spend our money here and just left after he did not wanting us to taking pictures of his "broken down fences". So if you want to spend an hout on a pony ride with this guy go ahead but you have been warned. read more

My husband and I planned to go to the Rockies S Ranch for a horseback ride for our anniversary. Bill was attentive prior to the reservation with securing a time and plan for an excellent horseback ride. We enjoyed 1.5 hours along the ridge and we had an excellent view of the Allegheny Mountains. We even had the chance to go up and down the ridge And cross two bodies of water. This is one of the best horseback rides I've ever had. read more

The Rocking S Ranch - Horseback Riding Near Me - Winchester, Virginia

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What a wonderful trip! You are on a ranch with the rancher and his horses. He has full knowledge of what "no experience" in horseback riding means. Not his first rodeo I guess! My daughters, 8 & 11, and I went today and had a blast. Memories that will last forever. Beautiful scenery too. read more

The Rocking S Ranch - Guess who's the photographer? You guessed it. Your guide, Bill. - Horseback Riding Near Me - Winchester, Virginia

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Bill was super accommodating and patient with our Teen Girl Scout troop! This event was a highlight of our weekend and one that we will be talking about for years to come! Worth every penny and the horses are gentle and perfect for a first-time rider. We will be back! read more

My wife and I had little to no riding experience. Well now we have a little more! This is a great place. The phone number is Bill's cell, and if he doesn't pick up he'll definitely call back. Very laid back and simple place but excellent rides and gentle and very well trained horses. The trails are varied in scenery and terrain, including marshy/wooded areas, a creek, inclines, gravel roads. This is a true small business in a fairly remote area. Beautiful country driving to get there and beautiful property as well. Highly recommend it! read more

The horse and trails we went on were great, but the guide was very unprofessional. He talked numerous times about previous guests telling how they were wrong. We were charged for an hour and a half ride and were only riding for an hour. When asked about it we were told we left at 1:40 and returned at 3:10. We had pictures on our phone as late as 2:06 when the last person was getting on their horse. So we were overcharged and weren't told the truth when we enquired about the time. read more

My girlfriend and I decided to take a trip to the Rocking Horse Ranch, after spotting a brochure around the Winchester area. The experience was better than expected. The owner Bill was an exceptional tour guide and we both loved his friendly attitude and light hearted jokes. We definitely recommend this place to anyone, just factor in 2+ hours of total time riding/setting up. read more

Great service, chatty guy, lovely scenery. Enjoyed the easy ride through the woods and along a nearby stream. Guide - owner - took great photos (don't have access to them today, sorry!). And the horses were clean and easy to ride. read more

I booked a ride at Rocking S Ranch for my wife's birthday, and Bill made it a memorable experience! The area was beautiful, the ride was diverse and Bill captured some amazing pictures that we'll appreciate for many years. In addition to being a great guide and funny person, he had great recommendations for local food and lodging. Will be back for sure! read more

Such a wonderful outfit! Family run and exceptionally great for the kids as well as the adults!!! Bill is a fun and informative guide while his daughter Haley is as sweet as can be! Could not have enjoyed it more! You will want to come back again and again! read more

We had perfect weather for our trail ride! It was my neice's birthday and first time riding. She had a great time and loved her pretty horse :) This is a really nice family run operation. read more

If you're looking for a small, family operated ranch for hourly-rate horseback riding, I strongly recommend this tiny ranch. John and his two daughters are no nonsense, down-to-earth people with an obvious greater love for their horses than in their making money! Their initial interaction with you as a customer makes you feel more like a friend than a patron. The care they show their animals is better than any establishment with which I've dealt in my life. At roughly $40 an hour, we were initially skeptical but during our ride, John never looked at his watch, made us feel rushed, or gave the slightest inkling of us being anything other than the center of his attention. His routes were obviously well-known by him but did not resemble the "beaten paths" of most horseback riding establishments I've visited. Two words of caution however..... 1. John's one-liners are a bit tongue-in-cheek, light on the humor of today, heavy on the cowboy charm of yesterday. 2. This is a family run business - if you're expecting pomp and circumstance, aloof handling, city-flair, or anything other than a good old-fashioned horseback ride with a lot of idle conversation - go somewhere else! These are good hard-working people who obviously love what they do. read more

We had a great time! My daughter is a good rider and I'm a beginner and we both had a lot of fun. Bill, the owner, is a hoot! And he is a great teacher too. I would highly recommend this if you just want to have a couple hours of low-key sight seeing fun. And the horses are really responsive and friendly. Bill described other tours he can take you along that are more challenging. If you are a good rider you'll probably find Bill has a perfect trail for you too. read more

Great family adventure! Well mannered horses, fun wranglers, pretty scenery, call ahead. Took the grandchildren (6, 8, 18) for their first ever ride with their experienced but stove up granddad (70+), who received extra help mounting. Bill and Hailey are exceptional guides, providing a fun and safe intro to horsemanship. Bill took many pictures for us, and there are happy faces all around. Creek riding even broke the sangfroid of the 18 year old, he had so much fun he forgot himself and smiled in almost every picture. This working ranch trail ride is a top notch memory maker; we'll be going back again.. read more

We took our 3 boys and my 72 yr old father for a ride. Bill was fantastic!!! He and his daughter were GREAT with my boys!!! He accommodated my father who needed a great deal of assistance mounting and dismounting the boys. They loved the trail and going through the creek!!! read more

Bill was great. We very much enjoyed the ride and will be back! Horses are very tame and definitely good for anyone from beginner to the pro. read more

Bill is a great guide and has a great little operation. The horses are well taken care of and the trail ride itself was awesome! Not your typical nose to tail boring ride. He took us through beautiful terrain, gorgeous views , and even took photos for us! He is a fun and friendly man with a great personality, funny stories, and sense of ease to him. I can't wait to go again. read more

This is a wonderful place. Bill was happy to accomodate our schedule in Winchester and meet us for pony rides for my three girls, ages 4, 8 and 11. He was warm and welcoming and even though it was our first time, it felt like we were meeting an old friend who just happened to live on a horse farm. We will certainly return. read more

First time riding a horse and really enjoyed it. Bill - the tour guide/instructor was very charismatic and told us everything we needed to know. He told lots of jokes and kept the ride fun. He also took plenty of really great action pictures of us throughout the trail ride. I highly recommend this for any beginner riders and would definitely return. read more

You can't get any better than Rocking S Ranch for horseback riding! I surpised my fiance with a fun day of horseback ridiing. He has never been on a horse before and was a little nervous to say the least. Bill, who is the owner and our guide, made us feel at ease and we were really able to enjoy the ride. You can tell that Bill really enjoys what he does and takes it upon himself to make sure veryone is safe and has a good time. He even took our phone to snap a bunch of pictures while we were riding! Bill was very easy to talk to and i enjoyed his one liner jokes. We are already planning to go back this fall. Thanks Bill for a wonderful day! read more