The Ultimate Weekend Guide to Ocala, Florida

Vacations to Florida are often filled with white sandy beaches and theme parks. However, a few days spent in Ocala will provide the same adventurous weekend at a fraction of the cost. If you’ve traveled I-75 through Florida, you’ve likely passed Ocala to get to your destination, and maybe you didn’t even realize it. 

Located 35 miles south of Gainesville, Ocala is known as “horse country.” Along the busy interstate, the swampy woods open into the perfectly manicured pasture and freshly raked racetracks as far as the eye can see. If you’re not careful, it’s easy to drive through this horse haven and end up being swallowed by the untamed forest on the other side of the county line. 


Where to Stay

Glamping at Enchanted Oaks Farm

Staying at Enchanted Oaks Farm was the catalyst for my stay in Ocala. This Instagram-worthy glamping Airbnb just off the interstate has been on my Airbnb favorites list for over a year. The stars finally aligned for me to book my stay, and it did not disappoint. Over ten rental houses on the property include off-the-grid A-frame houses, a treehouse, a lake house, and retro RVs. I booked the teal camper RV for my stay. These rentals do not come with all the comforts of home (unless you already live an off-the-grid lifestyle), but they do provide a comfortable place to sleep and unplug from the world. 

The aesthetically decorated tiny homes drew me to Enchanted Oaks Farm, but the best part is the animals on the farm. At any given time, there are a variety of animals to visit; but these aren’t your typical cows and horses. Enchanted Oaks is home to llama, bearded goats, and mini cows, not to mention the real star of the farm, Zippy, the zebra. Visitors are encouraged to bring carrots to feed the animals during their stay. Some of the farm’s Airbnbs provide direct access to Zippy’s pen (talk about the perfect morning wake-up call). Other rental locations (like the lake house and treehouse) are a bit more secluded, allowing for a quiet morning watching the sun rise over the oak trees. 

Luxury at the World Equestrian Center

Glamping isn’t for everyone. If luxury accommodations in a stately hotel are the way you prefer to travel, look no further than The Equestrian Hotel at the World Equestrian Center. I was overwhelmed by the size of this venue. The World Equestrian Center is an expansive facility spanning over 300 acres to provide the best experience for the horse, riders, and spectators who come to cheer them on. The events calendar is always filled with various competitions on the property. The two exposition centers are flexible indoor spaces that can be transformed to host sports competitions, automobile showcases, and canine shows. In addition to the expo centers, there are also 16 outdoor arenas, five indoor climate-controlled arenas, and accompanying stable facilities. 

The World Equestrian Center is the epitome of equestrian activities and competitions. The jewel at the center of the property is the Equestrian Hotel. The hotel’s opulence starts in the grand lobby, where 20-foot ceilings are adorned with shining crystal chandeliers. A roaring floor-to-ceiling stone fireplace provides a warm focal point, inviting guests to gather around. Many of the 248 rooms face the Grand Arena allowing guests to watch the competitions from a bird’s eye view. 


The dining options on the property are nothing short of exquisite. Stirrups is the premier fine dining restaurant within the Equestrian Hotel. Exquisite prime steak, fresh Florida seafood, and seasonal southern-inspired dishes are served against a backdrop overlooking the grand arena. Even if you aren’t a hotel guest, dining at Stirrups would be an excellent place for a special date night or celebration.  The more relaxed dining option is Yellow Pony Pub & Garden. Here guests can enjoy live music on the patio, signature cocktails, and shareable appetizers and entrees in the lobby lounge. 

The Calluna Spa and Salon has everything you need to rejuvenate from head to toe. This 7,000-square-foot facility offers spa packages, including massages, manicures, pedicures, and hair styling treatments. The Calluna Spa is designed to leave you feeling refreshed and rejuvenated during your stay.

World Equestrian Center in Ocala Florida. A horse jumping through a gate in the main arena.
World Equestrian Center in Ocala Florida. A horse jumping through a gate in the main arena.

Things To Do

Gypsy Gold Horse Farm

If there is one place you must visit in Ocala, it’s Gypsy Gold Horse Farm. I wrote an extensive post on my visit to this farm, where the Gypsy Vanner horse is bred, in my Florida Farm Series – Florida Farm Spotlight: Gypsy Gold Horse Farm

Dennis and his late wife, Cindy, discovered the Vanner Horse while driving the countryside of Great Britain on a business trip in 1995. They were both enamored by the beauty of a stallion (named Cushti Bok) grazing on the hillside, prompting them to stop by the farmer’s house to buy the horse in the pasture. This decision started them down a path that would introduce them to the Gypsy culture and lifestyle in Great Britain, making lifelong friends with the breeders and eventually bringing sixteen Gypsy Vanner Horses to the United States and creating the Gypsy Vanner Horse Society

Cactus Jack’s Trail Rides

After spending the morning around the Gypsy Vanner horses, you may be itching to try your hand at horseback riding. You won’t have to travel far. Just three miles north of the Gypsy Gold Horse Farm is Cactus Jack’s Trail Rides. Ranging from 1-2 hour trail rides, visitors will enjoy guided tours across the Cross Florida Greenway, including crossing the Landbridge Trailhead that spans over I-75. 

There are 52 horses available to ride at Cactus Jack’s, most of which were rescued or donated. Whether you’re an experienced rider or a first-timer, there is a horse who can take you on a journey through the preserved Florida woodlands.


Fort King National Historic Landmark

On a seasonably comfortable day, visiting Fort King is worth an hour or two of your time. Fort King was a central military post during the Second Seminole War. Today, the site educates and informs the public of the park’s significant history, cultural, and natural resources. 

The unrefined wooden fort is a replica of the one built-in 1835. Annual reenactments are held within the park to provide a living history of the events during this era. I didn’t visit during one of the special event days, but the fort had plenty of educational signage with photos and QR codes to make history come to life. 

An easy 0.7 miles hiking trail along the park’s perimeter, takes visitors through the same wooded area soldiers used to gather resources to sustain the fort. Educational signage is also posted along the trail for a self-guided history of Fort King.

Outside the Fort King National Historic Landmark.

Silver Spring State Park

Silver Spring State Park has been on my State Park bucket list for a long time. I was finally able to check it off my list during my stay in Ocala, but I will have to come back again to fully enjoy all the park’s activities. I rushed across town to make the last Glass Bottom Boat Tour of the day, leaving little time to explore every trail before sunset. 

When traveling on I-75 in Ocala, advertisements for the Silver Spring’s Glass Bottom Boat Tours begin to fill every billboard. Operating since the 1870s (that’s not a typo, they have been doing these tours for over 150 years), the Glass Bottom Boat Tours were the original tourist attraction in Florida. Visitors from all over the world have crowded into these wooden boats to peer down into the crystal clear water below. The captain of the boat drives to notable springs along the river, reciting the circumference and gallons a day each spring pumps into the river, ending each stop with a joke they have told for the millionth time that day. 

The glass at the bottom of the boat is like looking into an aquarium. Turtles and fish seem unfazed by the hovering boat circling overhead. The captains expertly kept the boats circling over each spring, allowing everyone to stare into the springs where movies like the Creature from the Black Lagoon, Rebel Without a Cause, and Tarzan were filmed. Once upon a time, this was Hollywood’s go-to place to film underwater scenes for movies. The clear blue water provided the best visuals for making the audience believe the characters were deep in the ocean. 


The Glass Bottom Boats are the main attraction; there are many other park activities to enjoy. Kayak, canoes, and stand-up paddleboard rentals are available to float down the five-mile Silver River. As long as you don’t rent a double kayak, your paddle down the river will be peaceful and allow you to enjoy the quiet of the untouched Florida wilderness. If you prefer to stay on land, there are various hiking trails ranging from one to four miles. 

If you haven’t gotten enough of the reenactments at Fort King, Silver Springs also hosts tours at Cracker Village on the 2nd and 4th Saturday every month. Allow yourself to be transported into the 19th century when life in Florida wasn’t shining highrises and trendy restaurants. Life on the homestead was slow, and survival depended on the crops and community within your village. Also open on the weekend is the Silver River Museum. The focus is less on the lives of the first settlers in Ocala and more on this area’s geology, paleontology, archaeology, and natural history. 

The Canyons Zipline Adventure Park

Canyons Zipline Adventure Park is a one-stop shop for a day of adventures. Not only do they have 1-3 hour ziplining courses, but they also have horseback riding through the 100-acre property and kayaking on the Lost Springs Lake. There is something for everyone among the variety of activities. Those kayaking the lake will experience a guided tour along the unique canyon wall as people fly overhead on the zip lines. Since Ocala is horse country, this is the perfect place to experience the wilderness on horseback. Guides will lead you along the canyon walls and to Lost Springs Lake. The scenic vistas, moss-covered woods, and enormous cliff walls will leave you feeling transported far away from the typical Florida landscape.  


Where To Eat

Downtown Ocala Square – Ivy on the Square

Between the trinket shops and home décor stores, there are many restaurants and bars to choose from in Downtown Ocala. I walked the square several times before deciding to eat at Ivy on the Square. The tipping point was the high google ratings and an inkling the bar could make a quality bourbon drink. The décor was a dark eclectic industrial feel paired with warmly lit chandeliers. The evening was a bit cooler than usual, and I decided on the French Onion Soup and old-fashioned as I sat at the crowded bar. The soup had the perfect amount of onions to cheese ratio, and the old-fashioned was as I had hoped; since it was made with one of my favorite bourbons, it would have been hard for me to dislike it. It was exactly what I needed after a long day of crisscrossing the city. 

French Onion Soup and old-fashioned at the Ivy on the Square in Ocala Florida.

Whispering Oaks Winery

Whispering Oaks Winery offers more than a glass of antioxidant-rich blueberry wine. The winery campus is more of an event space capable of hosting a wedding or large gathering. A full kitchen serves tapas and flatbreads during lunch, and Friday and Saturday nights are steak night. A rotation of live entertainment is also hosted on the outdoor patio during the weekends. Dinner reservations for steak night fill up fast; book early if you plan on stopping in. 

Winery tours are offered during the weekdays when available. Tours are not always guaranteed, but they take reservations to ensure a tour can be accommodated if you have a specific day and time of arrival at the winery. Just by chance, I was able to catch a brief tour from one of the owners during my stop-in. I was shown the complete process of turning blueberries into award-winning wine. Afterward, I sampled the four wines while watching koi swim in circles in the patio pond. Stopping at Whispering Oaks is a great midday stop to slow down under the oak trees and enjoy the quiet before racing off to the destination.

The entrance to Whispering Oaks Winery.

The information in this article was accurate when published but can change without notice. Please confirm rates and details when planning your trip by following the links in this article. If you find out-of-date or inaccurate information, I’d love to hear about it to update the article. Use the comments section below. Thanks! 

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