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    Diane's Riding Place

    4.9 (43 reviews)

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    Jeff G.

    Diane and he assistant were super helpful and they clearly love what they do! They horses are clearly being taken care of properly and are loved! The grounds are well maintained and the trails are fun for what they are! My daughter is 3.5 yo and did phenomenally on Mr Bill! He was a sweet 27year old pony! This was the only place I could find I was willing to let a rambunctious 3 1/2-year-old get on the horse! Everywhere else, they wanted them to be at least five years old for some reason! to me this place is awesome. I highly recommend it and I will be coming back again.

    Katie R.

    My daughter just had her first riding lessons at Diane's and loved it. Diane was super knowledgeable, helpful and patient. We can't wait to go back!

    Pony ride

    Absolutely love Diane & this place! We love coming every year to take my daughter and myself on a little pony ride! It's one of the things we look forward to every summer!

    Jen T.

    Vicky and the mini horse, Lilly, made my four year old daughters' day! We are from out of state, and my little girl has been begging to "go ride horsies". After a quick search on yelp, we found Diane's. Vicky was so great with my daughter. We did a quick 30 min "pleasure ride", and that was perfect. When we are back in the state again visiting family, we will definitely be stopping back by!

    Exploring the Tac Room

    Took my 4 1/2 year old grandson to Diane's yesterday. He's been Horse Crazy since he was 2 or younger. He loved touring the Barn, seeing all the horses, the arena, the Tac Room. Most of all, his first Pony Ride on Mr. Bill. This was a Life Memory event for him. Diane did an amazing job with him. I can't imagine how many times she's done this for kids of all ages. She's an amazing person. Very safety conscious, instructional, fun and enthusiastic. I highly suggest that if you have a horse enthusiast in the family, take them to Diane's. There's a reason she's been doing this for so long. She's excellent at it. I'm sure we'll be back when ever my grandson comes over to central Oregon to visit.

    Ben E.

    I had an amazing time with my wife and would highly recommend this place! We really enjoyed the ride around Diane's property, she was great with our son as well and our whole family enjoyed our time there. Diane is very kind and even a great photographer!! Thank you for the great memories made & we will be back on our next trip to Oregon.

    Jen K.

    This feels like a full circle review. After riding at almost every other place in the area, the consensus is that Diane's is the best. She is an awesome lady, fantastic with the kids and provides a very positive learning environment. While I still wish there was a little more of a trail ride experience, after having one child traumatized on a trail ride at another place in the area, I've come to really appreciate the experience here.

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    1 year ago

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    Business owner information

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    Diane S.

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    13 years ago

    Great place for a ride! Diane is a hoot and the setting is fantastic. Good value too for a one hour ride - my daughter loved it

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    Page 1 of 2

    Ask the Community - Diane's Riding Place

    Review Highlights - Diane's Riding Place

    This was the only place I could find I was willing to let a rambunctious 3 1/2-year-old get on the horse!

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    Brasada Ranch Equestrian Center

    Brasada Ranch Equestrian Center

    4.5(24 reviews)
    14.0 mi

    I sent the following email to Brasda Ranch regarding my experience. I received NO response. Very…read moredisappointed in their lack of good customer service - especially since I had to pay the "gratuity" ($90) when I schedule our trail ride. Wed, Jul 23, 1:58PM "I'm reaching out to let you know what a disappointment my ride was on Sunday. I was partnered with Medicine Bow for the ride. I'm an experienced rider and own two horses myself. I didn't find out until after the ride that he is only four years old - which may explain his green behavior. I really don't find it enjoyable to constantly be pulling on a horse's mouth while they are trying to go their own way or getting too close to other horses. He's already got a hard mouth and I'm sure it's going to get worse. Putting experienced riders on this horse for an hour at a time is a poor excuse for proper training. I sincerely hope you do the right thing for this young horse before he's ruined.

    We decided on Brasada Trails for our horseback riding this trip. We stayed in Bend and enjoyed the…read morelovely drive out to to Pilot Butte. Our trail master Piper and her amazing guide horse Pepper took us on a beautiful ride up to a lookout where we enjoyed the best cinnamon marshmallow s'mores and a little break. On our way back we got the same wonderful views, and we had an overall amazing time. Super relaxing, the horses were great, and Piper made the experience super fun. Will definitely be returning!

    Photos
    Brasada Ranch Equestrian Center - One of the wranglers was nice enough to take a picture of us after the ride

    One of the wranglers was nice enough to take a picture of us after the ride

    Brasada Ranch Equestrian Center - Our horses for the 9:00 am ride

    Our horses for the 9:00 am ride

    Brasada Ranch Equestrian Center - Wrangler with Cisco  leading and my granddaughter with Dallas

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    Wrangler with Cisco leading and my granddaughter with Dallas

    Smith Rock Trail Rides - Me & Hubby with Slim & Sunny

    Smith Rock Trail Rides

    5.0(13 reviews)
    16.4 mi

    Our experience with Smith Rock Trail Rides was amazing. Brian was kind, fun, and attentive--an…read moreabsolutely amazing person to have lead these trail rides. He gave us great directions on how to ride and lead our horse, and stopped many times to take photos of our group. The views were GORGEOUS. Butterflies everywhere. They also have an adorable little puppy that made our time there extra sweet. I will definitely be coming back! Thank you!

    This is an absolute must-do if you're thinking about visiting Smith Rock. My husband and I have…read morehiked Smith Rock before, but being able to see it on horseback is just a whole different experience. The trail itself gets you up close to the rock formations of Smith Rock. Let me tell you, the scenery, the canyons, and the gorge that you get to see are spectacular. I really like how this company only does one ride a day and keep the groups small, we had only 5 ppl in our group. It kept things less hectic and I felt safer knowing our guide was able to keep an eye on all of us. Our guide Brian was super helpful and knowledgeable. He made sure you were comfortable on your horse and was very thorough with his instructions on the basics in order to enjoy your ride. He also gets extra points for taking great photos! We got to ride Slim & Sunny. Both horses were really sweet and easy to ride. You could tell Brian and his wife Melanie take great care of their horses. They know them pretty well and match each rider to their horse. No matter your experience level, I think anyone will have a good time and smith rock trial rides makes sure of that :)

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    Smith Rock Trail Rides
    Smith Rock Trail Rides
    Smith Rock Trail Rides

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    Long Hollow Ranch

    Long Hollow Ranch

    4.5(14 reviews)
    14.0 mi
    $$

    Long Hollow Ranch provides a taste of the Old West and appeals to visitors fondly remembering those…read moreold John Wayne westerns and life on the range. The majority of their business is focused on guests who are staying at the ranch (many from overseas) who want to go on longer trail rides or an old fashioned cattle drive a la City Slickers. Since we already have a home in the area, we didn't get to take advantage of their hospitality as guests. However, we did visit to enjoy a trail ride. My boys love to ride, but it has been quite difficult finding a trail ride that satisfies all of our needs. We've tried Diane's Riding Place, but they tend to be more instructional. The stables at the Seventh Mountain Resort were only OK. My goal was to get more of an 'authentic' trail ride with a little bit of fun. We were only partially successful. First off, making reservations wasn't terribly easy. After calling the main business line, I was given a second number to dial for the stables. Since the focus is on their ranch guests, they don't seem to be overly eager to take outside riders. Fortunately, some of those guests had another activity planned, so we were able to arrange a ride. It turned out to be semi-private and Katie was a wonderful guide. You will sign a brief liability waiver, and riders must wear jeans and boots. The boots requirement was a first, but fortunately they have plenty to borrow at no charge. Children are also required to wear helmets. The ranch covers 600 acres, so they took a gentle ride up through the hills to enjoy the view of the Three Sisters. It was a good ride, but low on the excitement factor. No cantering or galloping, just an easy mosey up and back. Unlike the prior reviewer, the ride lasted exactly 60 minutes, so no complaints there. It is really disappointing that there aren't more horseback riding options in the area. These hills are filled with ranches, but due to liability concerns, very few open their doors to the public. We still feel like we are searching to find that magical ride. http://www.lhranch.com/index.php

    This place was EXACTLY what we were looking for on our way home from our family vacation. We…read morewanted somewhere quiet to lay our heads down, somewhere 'different' than the normal hotel scene, and a place that our kids would remember. The Long Hollow Ranch checked every one of those boxes. We stayed in the Homestead cabin, which had three beds upstairs, and one downstairs. The cabin had two strong window AC units, which were wonderful. The cabin had no TV, which was great, but did have a vintage stove that served as a table top for the in-room microwave. There's also a mini-fridge and a Keurig Coffee Maker. Beds were comfy, bathroom has hot water in the shower, and the decor was fantastic. The morning breakfast was signaled by a good old-fashioned dinner bell at the main house, which is beautiful. There were lots of hash browns, fruit, juice and more. They even offered to cook each of us an egg to order, which our son took advantage of. The breakfast was absolutely great. All in all, this place was well worth the price, which was already much lower than other places on our trip. They even let us dabble with our fly pole in their bass pond free of charge. They accommodated our late check in (10 PM) and even had the AC going when we arrived. Customer service was top notch. This is the definition of a 5 STAR property.

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    Long Hollow Ranch
    Long Hollow Ranch
    Long Hollow Ranch

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    Stables At Seventh Mountain Resort

    Stables At Seventh Mountain Resort

    3.7(16 reviews)
    13.1 mi

    My boys love to go horseback riding, but it was a bit of a challenge arranging it during our visit…read moreto Bend. Most of the places we've gone to in the past (Crooked River Ranch and Eagle Crest Resort) were closed this summer, so we decided to make the drive to the Seventh Mountain Resort by Mt. Bachelor. We had a terrible experience trying to make a reservation. So up to the actual trail ride, I would give them one or two stars for the administrative side of the business. Nonresponsive by phone, a bit disorganized in person and they overcharged us for the ride until we called the discrepancy to their attention. Once we got on the horses, things improved from there, slightly. The ride is a bit dusty and not the best we've ever had, but again, there appear to be very few options in the area. Unfortunately on a trail ride your experience is very dependent on other riders and whether they are comfortable and able to control their horse. We had two other riders that almost fell off and unfortunately it really freaked out my son. We've gone to Diane's Riding Place, which I now consider the best in the area, but it is more instructional rather than a trail ride. So at the end of day, a fun family activity, but hopefully others will have a better experience before mounting their steed. They also have adorable miniature ponies at Pony Town, so that would be a hit with little ones.

    A great first time horseback riding experience for my 6 and 8 year old girls. The horses (Frosty…read moreand Maverick) were gentle and perfect for them. Ari was a great guide for the girls as well, engaging and calming. Nice trail ride through the trees and near the river.

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    Stables At Seventh Mountain Resort
    Stables At Seventh Mountain Resort
    Stables At Seventh Mountain Resort

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    Diane's Riding Place - horsebackriding - Updated May 2026

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