1. Highland Farm

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Middleburg, FL

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Highland Farm

4.3 (16 reviews)
Open • 9:00 am - 9:00 pm

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On the farm
Shayla B.

I never thought that I'd see myself horseback riding, but I did it right here at Highland Farm! I went on a trip to St. Augustine last year with my family and my Mom ended up planning a horseback riding trip for us in Middleburg which is about 45 minutes away. It's located on a huge ranch and there is no designated parking, so we just parked close to the training stable. Kirk was our trainer and he was awesome! You can tell that he is very passionate about what he does. He's trained many professional horseback riders and used to ride professionally himself! Since it's on a farm, you'll see all kind of farm animals roaming around. We saw a few ducks and a some dogs, and of course the beautiful horses! We got to feed them as well, which can be kind of intimidating, but it was really quite fun. For the practice run, there is a small section where you will get seated and adjusted for your horse. Here, you will learn how to hold the ropes and how to speed up and slow down the horse. You will do a few practice laps and then you will transition to riding throughout the ranch. We weren't as adventurous as many other groups you can say, but we did circle around the ranch a few times until we were tired. Kirk was super attentive and patient with us, and he even let us stay longer than out allotted time! He really made my first time horseback riding super fun and enjoyable!

Winter riding.

Kirk was incredible. Very patient and knowledgeable. Horses were cooperative. Nice being able to ride around the seven acres. FYI Kirk has lots of riding options. Call and tell him what your interests are and he will tailor to your liking. He even does beach rides.

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Review Highlights - Highland Farm

“My youngest granddaughter is 2 and Kirk was gentle and helped her feed the horses and other animals.”

Mentioned in 10 reviews

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Diamond D Ranch - Honey the mini horse

Diamond D Ranch

(22 reviews)

Westside

First time here last weekend for the Family Farm Day and we had a blast! It was pretty easy to find…read moreyou just follow the signs that point to parking. People with reflective vests will tell you where to park so it's smooth and easy to get out when you need and no one is blocking you in. We ordered our tickets online and they were in my inbox within 5 minutes of placing the order. We signed the waivers and the young ladies at the desk scanned our tickets. They gave us a map and wrist bands. The map tells when the nature walks will take place and there's also a speaker system in the pavilion and other places to hear announcements. The only thing we didn't get to was the cow milking (not a live cow) and the nature walk but we weren't too disappointed because the highlights were the pony rides and feeding the bison and cows! It was clean and everyone was helpful. My daughters and I went to one of the restrooms but the women's was clogged with toilet paper - when we stepped back outside I saw a worker and flagged her down to let her know and she said "oh thank you!" And got right on the walkie talkie and within minutes had one of the men over there and it was fixed. Meanwhile we went to another restroom just down the walkway. We bought T shirts and a tumblr, had some BBQ and milkshakes.. all was delicious and wonderful! Would definitely go back again. Well worth the money for my family of 4 to have an epic day!

I went to Diamond D. For a school field trip it was nice and the kids had fun. This place is good…read morefor small kids.

Makin' Tracks Trail Rides - Me and Kit!

Makin' Tracks Trail Rides

(19 reviews)

We had a great time! The folks at Makin' Tracks made us feel right at home. They love their horses,…read moreand it shows. Our trusty steeds knew the trails as well as our guides, and they're experienced enough to use hackamores instead of bridles and bits. The specific trails these guys took us on were amazing. From Sawgrass marshes, to scrub forests to oak hammocks, we loved the diverse Florida scenery. We saw tons of birds, including some elusive wild turkeys and even a deer or two. Don't forget to ask to see some long forgotten infrastructure from the defunct "Cross Florida Barge Canal".

This place had great reviews on Yelp so I went for it! It was slightly underwhelming for what the…read moreother reviews were saying. It was an experience to be in the rural country area of Florida. Time stops here so don't expect everything to be as the time slot shows. It's a dirt road out to a house with a little old sign that barely appears to be the business. We pulled in and looked around for the owner and eventually found him preparing everything for our ride. It took some time standing around waiting for some of this family to arrive to go on the ride with us. In the mean time we let the goats and chickens and horses. All the horses look well taken care of and all the animals seem happy so that was a good sign. There's a definitely a moment of "what did I get us into" when we pulled up to the barn and saw the behind the scenes and waited around a bit for them to load everything up into the trailer. We followed them to the trailhead in our car and then saddled up and headed out. I've been on better trails before for the ride so it was a bit underwhelming, but the Florida foliage was unique and pretty. Our guide was training a new lead horse so we had a few jumpy moments, but he knows what he's doing and showed us his training skills. All our horses were very well behaved and felt safe to be on. Overall, it's definitely a novice business and nothing special, but the opportunity to interact with some real country folks made it feel authentic and was neat.

Highland Farm - horsebackriding - Updated October 2026

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