My spouse and I both have some experience with horses, and wanted to take a good trailride together--and we hit the jackpot with Hollingsworth Horses. Hollingsworth Horses offers both guided and unguided riding. This is a small operation (they run 12 horses), so make reservations in tourist season--and be prepared for a wonderful experience: Instead of the typical guided ride, where you follow along the proscribed path after the guide, horses nose to tail, we spent half and hour or so in riding prep, helping to saddle our horses, then spent half and hour or so in the ring, where we learned out mounts' personalities. Lynn matched us to the horses, based on our experience and the horses' traits, taking plenty of care with the process. Then we look off on our own. The property is 122 acres of gorgeous Black Hills country, with Black Hills National Forest access as well as Mickelson Trail access--between the three, there's plenty of beautiful country to explore. Our horses were well behaved, but opinionated enough that we did need to actually RIDE--not like the nose-to-tail trail ride at all! They were calm but alert when we encountered bicyclists on the Mikelson, manageable when we encountered pastured horses along the way, and stood and handled well when we went through gates and so forth, having to dismount and remount. While we didn't take a guided ride, going out with a guide in a family group is VERY different from a "we'll leave when we have 10 riders" operation--This is personal service, geared to the individual group. We highly recommend this to anyone looking for a terrific couple of hours on horseback. It's a lovely facility, gorgeous country, and the care taken with the horses and facility carries through with the care taken with customers--little things like: Per hour charges don't begin until you leave the ring--and you don't leave the ring util you're comfortable with your horse... If the horse and you don't seem like a good fit when you leave the ring, they'll swap out for you. They watch how you interact with the horse, and can tell a lot about your skill level that way. We highly recommend Hollingsworth Horses! read more

Hollingsworth Horses was the best part of our trip to South Dakota. My fiancé and I visited back in July. Christin took us on a 2 hour ride around the property, which was absolutely incredible, up hills, and huge glacial boulders, through bogs and fields, meeting all sorts of wildlife along the way (whistle pigs!!). Being from NYC, it was such a breathtaking and awe inspiring experience, which was made even better by our guide Christin, who talked to us about the area, history, as well as her family, the horses, and music....it was amazing, and by the end it felt like I was riding with an old friend. My fiancé had never ridden before and was matched with a sweet pony, black jack. Christin gave him pointers in the round pen on steering and equitation before we left to ensure his comfort. I'm a horseback riding instructor and ride regularly, but as a hunter/jumper I still happily took some pointers on western riding. I was matched with Brown Sugar, (a cute sturdy girl with a funny little habit .... flipping the shank of the bit in her mouth....it was funny and I didn't mind reaching to pull it out every so often!) Christin showed off the rest of her gorgeous herd (Christin if you are reading this I hope you got that Belgian you were looking for!). The horses are all well cared for, well behaved, and happy, freely roaming the vast property. We hope to one day be able to return and ride the rest of the Hollingsworth herd. This is an amazing experience, no nose to tail trail ride at all, you are riding freely on fully alive animals and it is an experience like no other. read more

Wish we could choose 10 stars! This was our 2nd visit, the first time being in 2021. We loved it so much that we had to come back!! First of all, today as we were getting checked in our daughter Mattie, lost the back of one of her earrings. Wrangler Nichole went out of her way to fetch one of her own earring backs for Mattie, that was so nice of her! That being said, HUGE shout out to our tour guides, Brandon and Nicole, they took the time to match us up with the personalities of each horse and also showed us how to properly maneuver during the ride. Throughout the ride, we learned about the history of the beautiful property as well as the vegetation, and the rock formations. Our kids were eight and nine the first time we were here, and ten and eleven this time. Whether you're an experienced rider or a first timer, these two guides and the gentle horses will make you feel safe and secure while you experience the adventure of a lifetime. If you ever find yourself near the Custer SD area or are looking to have an experience that you will never forget, make sure to book an appointment at this wonderful place! Once again, thank you Brandon and Nichole for teaching us the basics and having incredible hospitality and patience with us. And of course you can't forget the amazing horses, Maze, Brown Sugar, Checkers, and Scullyott. We can't wait to see you next year! Can't thank you all enough for such a memorable experience!! read more

After researching horseback riding in the Black Hills area, I made reservations with Hollingsworth Horses several weeks before our trip to SD by calling Christie - she asked questions about our group and gave concise information about the experience. She asked for us to give a call one day in advance, to make sure weather would be fine and the horses were in good condition (not wet, sore, etc.) We did so, and Christie was wonderful. She also gave alternate directions because GPS would not be correct. When we arrived, we were greeted by Kristen and Meghan, and they spent a lot of time giving us info about our horses and their quirks (I rode "Snack Jack" aka Black Jack - who loves to pause and graze during the ride). I have ridden before but thought it would be fun to bring my two sons (19 and 11) for their first time. The wranglers were kind and patient. Our horse ride went for slightly over an hour, but plan on set up time and time in the ring. We were there for just under 2 hours. Wear tennis shoes at the very least, and long pants. Don't forget sunscreen. It's probably best if you have a fanny pack for your phone - it will fall out of your pocket! If you're staying in Custer, it's a hop and a skip, but we had to drive for about an hour from Rapid City. All in all, highly recommend Hollingsworth - the extra money was WELL worth it. read more

We went riding here on a guided tour in June, 2016. We have an 8 year old who never rode horses and wanted a private tour so that we would not be rushed. This was a simple but nice operation where you get exactly what you are seeking-- knowledgeable guide, beautiful scenery and a private tour on horseback through the Black Hills of South Dakota. Kristie the wrangler/guide was an experienced horse person who explained things thoroughly to us and took her time, letting our son ride on his own and even galloped or loped. She didn't mind if we stopped in scenic spots and took pictures of us. We thoroughly enjoyed this experience. We did an hour ride which was plenty for us since we do not ride all the time. The Hollingsworth property was only a few minutes away from downtown Custer, so it was easily accessible from Sylvan Lake where we stayed. We were able to fit in Crazy Horse Memorial and horseback riding, plus the scenic loop all in one day. read more

We arrived earlier than scheduled and got to see all the horses herded in, running out of the woods to the corral area, beautiful sight. You could tell these animals are well cared for. Kristin, the lead wrangler, is a joy to be around. We talked about our experience levels and then she matched us up perfectly with a pair of horses. Kristin really knows her stuff, she knows each of the horses down to their personalities. Kristin rode with us for a while giving us a few pointers. Then we were on our own. Absolutely the best horse riding experience we have ever had! If you are in the Black Hills area, this is the place to go for horse riding. read more

Fantastic Ride! We were camping in the Custer area and booked the one hour ride. It was wonderful! Kristin and owner Lynn were our guides. We had varying experience levels and they made sure we were all very comfortable. Lynn has a fascinating history and my son and I enjoyed speaking with him immensely. The other members of my family were closer to Kristin and I heard lots of laughter. Although we booked for one hour they did not look at the clock and we never felt rushed. Kristin also took lots of pictures for us. This is not your typical nose to tail trail ride and if we are ever in Custer again we will go back to Hollingsworth Horses. read more

My sons and nephew have never ridden a horse, so I was hoping for a positive first experience. My expectations were exceeded within the first 10 minutes. Mercy and Megan were phenomenal at giving easy to follow instructions for my 14, 11 and 10 year old boys. The land we rode on was incredibly beautiful and wild, yet well cared for. The scents of wild sage, clover and sweet grass added to the whole wonderful experience. The battery on my phone died, and Megan was nice enough to take many pictures of us to send so I didn't miss out on a thing. I highly recommend coming for a ride and enjoy the beautiful sights! read more

We had an amazing time with Morgan and Lynn today! Even though we didn't have much experience, they made us feel completely comfortable with our horses. It was a really personal experience and great time for our family because it was only us on the ride. We all loved that we could roam a bit and there wasn't a strict path we had to follow, as there are at most other horseback riding places. Overall, it was a wonderful experience! Would definitely recommend taking your family here, I'm sure we'll be back next time we're in the Black Hills! read more

My daughter loves horses. We are visiting from SC and my husband found Hollingsworth Horses. I cannot say enough positive things about the experience. I particularly appreciate the time spent getting acquainted with our horses before the actual ride. Our ranger was both professional and personable during the ride, allowing us to go our speed, take photos, etc. He even got us trotting which sent my 10-year-old girl to the moon. Ahab and Mace were wonderful. I highly recommend this experience! read more

Truly the way to go for a genuine riding experience while staying near the Black Hills. Great ranglers: professional, patient and helpful. Just 20 minutes south of Custer and slightly off the "beaten path".... worth the effort to get there. This small and friendly family-run ranch is as close as possible to riding your own horse while away from home. The horses have personality, yet dependability...If you love horses and the beauty of the Black Hills .....Don't miss it !!! read more

My daughter and I had a terrific ride with Hollingsworth Horses! Our guide, Brandon, was so kind and willing to share his knowledge of local wildlife and the area. He took us on a nice ride around their beautiful property and allowed us some freedom to control our own horses in a safe manner. The horses are beautiful, gentle, and well taken care of. Would definitely recommend this to anyone looking for a nice horse ride while visiting the Black Hills. Thanks Brandon! read more

My wife and I took a "bucket list" trip to South Dakota this past May. Our last evening we decided to take a sunset ride at the Hollingsworth Horse Ranch. From the time that owner Christie helped us book our time slot to the time we rode with her daughter Kristin who took us on our ride, it was the highlight of our trip!!! And we got to see and do a lot on our trip, so that's saying a lot! They made us feel like "family." Thank you Christie and Kristen for the memory! read more

I wish I could give Kristen 10 stars!!! This was one of my daughter's most memorable experiences. She was able to accommodate our family on such short notice. This is a top-notch horseback riding business and I would 100% recommend them to anyone who's looking for a private horseback riding experience. We will be riding here again the next time we come back. Thank you for such a wonderful time! Our daughter claims this was her "best birthday gift ever". read more

Had a wonderful time with Kristen, our guide today with my daughter. She was absolutely wonderful. Our horses were amazing, the property was simply beautiful and signing up was simple. My horse, "Mare" was so sweet and my daughters horse "Ahab" was so chilled. I loved those horses. Kristen's mom, who helped me get signed up was simply sweet. This was an amazing experience. I highly recommend this place. read more

My son and I reserved a guided ride and it was wonderful. We've had minimal previous horse experience. Kristen offered expert and easy to follow instructions to acclimate us with the horses. The ride was very personal and relaxed and the scenery was beautiful. We certainly will be recommending Hollingsworth Horses to family and friends who visit the area!! Thank you for making memories with us!! Mary W. read more

From the beginning of planning my trip to Custer I had been looking forward to horseback riding. I was not disappointed! Great experience! We did the unguided because we have some experience. Horses were awesome, Madelynn our guide was great and very friendly as well as being a guide/leader. Very reasonably priced. Tack and horses are well cared for and beautiful. Will definitely be back! read more

This ride was the completion of my bucket list. They were very compassionate and accommodating to my need. They were very knowledgeable and matched us up with the perfect horse for our ride. Thank you so much for making my dream come true. It was not the typical nose to tail ride. They let me take my horse to a short gallop so I could feel the wind in my face. It was a perfect day. read more

We had a great time at Hollingsworth horses. We are inexperienced riders but Kristen explained everything to us and the horses handled really well. We had 4 riders and rode the horses Brown Sugar, Freckles, Scullyet and Black Jack. The ranch is beautiful and we saw a wild life throughout our ride. We had a really fun ride and will definitely do it again! read more