Pt 28 Ocala: Where History Rides and Legends Run
A drive-tour of history, horses and hidden gems through Ocala’s Charm
Step into a world where grand oaks whisper the past, wildflowers paint the landscape, and thoroughbreds gallop toward destiny. Ocala in spring is pure magic—let’s hit the road.
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After an amazing night’s sleep under a clear sky, our coach swaying gently like a hammock nestled among palm trees, I woke up feeling completely rested. The only thing on my mind? Experiencing Ocala.
I knew Ocala had made its mark in the mid-20th century as a leader in thoroughbred horse breeding, but I was curious—what about its history?
Long before European settlers arrived, Ocala was home to the Timucua people, an Indigenous group that thrived in northern Florida. Known for their elaborate villages and ceremonial mounds, they had a deep connection to the land.
The name Ocala is derived from the Timucuan word "Ocale," the name of a village encountered by Spanish explorers in the 16th century. It is believed to mean "big hammock" or "fair land"—a fitting description of the lush, rolling landscape.
In the 1500s, Spanish explorer Hernando de Soto led an expedition through the Ocala region in search of gold and riches. As was often the case with European conquests, their arrival of course disrupted Indigenous life, leading to conflict and the devastating decline of the Timucua population due to warfare and disease. However, the Spanish never fully settled Ocala, focusing instead on the coasts and major trade routes.
During the 1700s and 1800s, Florida changed hands multiple times between Spain and Britain before finally becoming part of the United States in 1821. By then, the Seminole people, descendants of Creek Indians who had migrated from Georgia and Alabama, had established themselves in the region.
Tensions escalated between the Seminoles and the U.S. government as settlers pushed into their lands, culminating in the Second Seminole War (1835–1842), one of the longest, most costly, and brutal conflicts in U.S. history.
Fort King, built in 1827, became a key military outpost and the site of multiple battles. After years of relentless fighting, most Seminoles were forcibly relocated to reservations in Oklahoma, clearing the way for American settlement. In 1846, Ocala was officially incorporated as a city.
Following the Civil War, Ocala became a thriving center for agriculture and horse breeding. The region’s mild climate and rich soil made it ideal for farming, especially citrus and cotton.
Then, in 1881, Ocala gained national attention as the host city for the Ocala Convention, where the Farmers’ Alliance, a national agrarian movement, pushed for economic and political reforms, ultimately influencing the rise of the Populist Party.
But like Seattle decades later, Ocala faced a devastating fire in 1883 that destroyed much of its wooden downtown. When the city rebuilt, it used brick instead of wood, earning the nickname "The Brick City."
By the mid-20th century, Ocala had already established itself in horse breeding, but one moment sealed its legacy. In 1956, an Ocala-bred horse named Needles became the first Florida-bred horse to win the Kentucky Derby. That victory launched Ocala onto the international stage as a powerhouse in thoroughbred racing.
Today, Ocala holds onto its prestigious title of "Horse Capital of the World," home to more than 600 thoroughbred farms producing champion racehorses.
But Ocala isn’t just about horses. It’s a haven for nature lovers, retirees, and adventurers alike. The area boasts:
Silver Springs State Park, home to one of the largest artesian springs in the world, where crystal-clear waters and famous glass-bottom boat tours reveal an underwater world teeming with wildlife.
Ocala National Forest, one of the largest national forests in the U.S., offering vast wilderness, hiking trails, and serene freshwater springs perfect for swimming and kayaking.
Between its rich history, thriving equestrian scene, and stunning landscapes, Ocala is a place where past and present intertwine beautifully. A city that, much like the horses it’s known for, continues to run strong. I could not wait to explore what it had to offer.
The first thing I do before venturing out is create a loop on Google Maps that includes grocery stores—it’s the geeky nutritionist in me!
It seems that Publix Super Market reigns supreme in this region. I counted nine Publix locations in and around Ocala. And on the topic of shopping, there is no shortage of it either, with all the popular box chains at your service.
But I’m always on the lookout for health food stores, natural grocery markets, and farmers markets, preferably local and, of course, with high-quality options.
Earth Fare, a chain found in the Carolinas, Virginia, Tennessee, and one in Ocala, Florida—perfect! This chain prides itself on sourcing local products and eliminating just about every type of chemical, additive, sweetener, and junk we don’t need in our food. They also offer all humanely pasture-raised animal products.
Just outside of Ocala, in The Villages, is The Green Apple Health Foods. They carry both food and supplements, so I was well taken care of.
Next, I needed to tap into farmers markets. Right downtown, just outside of the historic district, is The Ocala Downtown Market, open on Saturdays. The vendors are always changing but consistently deliver a diverse array of farmers, artisans, craftspeople, and food trucks. I’ve learned long ago—be there as soon as they open if you want something specific because within an hour, it’s gone.
There’s also a smaller farmers market, Circle Square Commons Farmers Market, on Thursdays. It has a lovely selection of fresh, seasonal produce from local growers, as well as baked goods, plants, and handmade products. The baked goods are how I get Ernie to tag along.
Essentially, hitting both of these farmers markets means not running out of fresh food for the week while also giving back to the local community I’m in.
So, with this in mind, I set up a day of just driving around, seeing what’s what, and ticking off things to explore. After all, we were going to be here a while, so I might as well line up my itinerary.
But for today, I settled on a weird-loop I started in Ocala’s Downtown Square. It is the heart of Ocala, featuring historic storefronts, a charming gazebo, and a lively small-town atmosphere. A great place to park the car and walk around and take in the history and a good wholesome lunch. Of course this is ticked off as a day of adventure in of itself. I also ticked off the beautifully restored 1941 Marion Theatre and Art Deco-style cinema with its original neon marquee sign.
Around the corner was Eighth Street, and I couldn’t wait to drive through Ocala’s Eighth Street Historic District. Since I was already there, why not?
It felt like stepping back in time, offering me a glimpse of that true Southern charm. Stately old homes stood proudly, their grand facades framed by towering live oaks draped in Spanish moss. There was an air of quiet elegance, as if this district had managed to preserve not just Florida’s architectural past but also the very essence of a bygone era.
With my windows down, I started my journey near SE 8th Street and Watula Avenue. Almost immediately, I found myself beneath a cathedral-like canopy of ancient oaks, their gnarled branches twisting overhead, forming a natural tunnel of green. The dappled sunlight filtered through the dense foliage, casting golden patterns across the street as I slowly (too slowly) cruised past grand Victorian, Colonial Revival, and Mediterranean-style mansions, each in pristine condition, as if they had been built just yesterday.
Adding to the surreal beauty of the moment were the azaleas and dogwoods in full bloom, splashing vibrant pinks and whites against the deep green of the oaks. It was breathtaking. I felt incredibly lucky to witness one of the most picturesque times of the year in this area, a brief and fleeting moment when nature seemed to dress Ocala in its finest colors.
I could immediately understand why this district was officially added to the National Register of Historic Places in 1984. Many of the homes here date back to the late 19th and early 20th centuries, built during a time when Ocala flourished as a center of commerce and Southern sophistication.
As I passed the Neoclassical Revival homes, I couldn’t help but imagine the stories they held within their walls. Majestic white columns stretched skyward, grand porticos framing the entrances in a way that reminded me of something straight out of Gone with the Wind. I could almost see a garden party unfolding on one of the grand wraparound porches—women dressed in stylish gowns, their delicate fans fluttering against the Florida heat, while the men, in their crisp suits and top hats, sipped sweet tea or perhaps something a little stronger. Laughter and conversation would have drifted out into the warm air, mixing with the distant sound of a horse-drawn carriage approaching along the brick-lined streets.
Then, as if stepping even further back in time, I came upon the John W. Pearson House, built in 1885. This Victorian masterpiece stood as one of the most impressive structures along the drive, with intricate gingerbread trim, an expansive wraparound porch, and towering turrets that looked as if they belonged in a fairy tale. I could almost see John and his family gathered outside on a warm spring afternoon, perhaps sitting on the porch with a pitcher of fresh-squeezed lemonade. Maybe his children played in the yard beneath the shade of the oaks, their laughter carried away on the soft April breeze.
Before I knew it, the homes began to shift in style. Mediterranean influences emerged—red tile roofs, stucco facades, and arched doorways, a nod to the Spanish Revival trend that swept through Florida in the early 1900s. These homes felt sun-drenched and warm, as if plucked straight from the coastline and placed gently among the oaks. Then came the cozy bungalows and Craftsman-style homes, smaller in scale but no less charming, each one exuding a sense of warmth with their broad porches and intricate woodwork.
The beauty of this drive wasn’t just in the architecture but in the feeling it evoked. The quiet streets felt untouched by time, the swaying moss overhead adding a rhythmic, almost hypnotic sense of peace. The only sounds were the chirping of birds and the occasional rustling of leaves, a stark contrast to the hustle and bustle just a few streets over.
I knew I had to come back just before sunset. The thought of these grand homes bathed in the pinks and oranges of a setting sun was too tempting to resist. And I can tell you, it did not disappoint.
Before heading back, I made a quick stop at Tuscawilla Art Park at 213 NE 5th Street. A hidden gem tucked away in the heart of the city, it was a beautiful blend of art, nature, and quiet reflection. I didn’t have time to explore it fully, but it quickly earned a spot on my ever-growing list of places to return to.
I rejoined the 21st-century hustle and bustle, the noise of modern life creeping back in as I left the historic district behind. But rather than getting lost in the clamor, I decided to take a detour. One that promised a completely different kind of scenery. I set off on a drive through Ocala’s Horse Country, a stretch of road where time slows down, and the landscape unfolds in rolling waves of green.
I began on W Hwy 326, a picturesque stretch that winds through the heart of Ocala’s "Horse Capital of the World". As I drove, the traffic thinned, and the busier parts of town faded away in my rearview mirror. Soon, I was surrounded by miles of pristine farmland, where thoroughbreds grazed under the shade of grand oak trees. The sight of foals frolicking alongside their mothers made me smile. These young horses, full of energy and promise, were under the watchful eye of their caretakers, each one hoping to one day join Ocala’s long lineage of champions.
With nothing but clear skies and golden sunlight stretching across the horizon, the landscape felt even more alive. The fresh green pastures, dotted with wildflowers, were almost too perfect, as if they had been painted onto the rolling hills.
Turning onto US-27, I entered one of the most famous equestrian routes in the country. This stretch of road is lined with elite horse farms, some spanning hundreds of acres. Many of the farms here train thoroughbreds for the Kentucky Derby, Belmont Stakes, and other international competitions.
The drive itself felt almost cinematic, the majestic white-fenced properties, the live oaks draped in Spanish moss, and the occasional glimpse of horses galloping in the distance. It made me want to grab an Ocala Old Fashioned, settle into a rocking chair on a wraparound porch, and just watch the world go by. Then again, I don’t really drink, so it would more than likely be freshly squeezed Ocala orange juice. You get my drift.
As I continued, I passed the Golden Ocala Golf & Equestrian Club, an exclusive luxury community that seemed to be a world of its own. Manicured lawns stretched toward elegant estates with expansive horse stables, all tucked behind pristine bridle paths that wound through the property. The golf course itself is world-class, featuring replica holes from Augusta National and St. Andrews, a dream for any golf lover. Even if you don’t set foot on the green, just driving by, you can tell that this is one of Ocala’s most upscale equestrian neighborhoods. The sheer grandeur of it all was something to behold.
And if you’re truly in the mood for a breathtaking panoramic view, I’ll let you in on a little secret. I took a detour onto NW 110th Ave, a quieter backroad that runs parallel to some of the most scenic horse farms. I couldn’t resist pulling over along the roadside for a moment of stillness—no cars, no noise, just the soft rustling of grass in the breeze.
The landscape was in full bloom, wildflowers bursting with color, swaying in the wind as if nature itself was performing a slow, graceful dance. The golden sunlight washed over the fields, creating an almost hypnotic effect, where the rippling grass mimicked the movement of ocean waves.
If I had an easel and some paint, I probably would have stayed for hours, trying to capture the way the light played against the fields, the contrast of deep green pastures against the soft pinks and yellows of wildflowers.
Circling back toward town, I made a few mental notes for later. Katya Vineyards—an upscale spot known for its locally sourced wines and farm-to-table dishes—was definitely on my list. It felt like the perfect place to unwind after a long day of exploring.
I also passed by Silver Springs State Park, famous for its crystal-clear waters and glass-bottom boat tours, and made a mental note to return when I had more time to take it all in.
For something more off-the-beaten-path, the Marshall Swamp Wildlife Management Area seemed like a peaceful escape, offering diverse wildlife and quiet natural landscapes.
And then, for a little nostalgic fun, the Ocala Drive-In caught my eye—a throwback to the golden days of cinema, offering a truly unique movie-watching experience under the stars.
As I headed back, I realized how easily Ocala balances its rich equestrian heritage with natural beauty, luxury, and small-town charm. Whether you’re soaking in the sights of horse country, wandering through historic districts, or floating on spring-fed waters, Ocala has a way of making you feel like you’ve stepped into a different world—one where the past and present blend seamlessly into something unforgettable. But remeber to have a silent moment for the battles and bloodshed that once covered these lands.
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Pt 25-From Pee Bottles to Peaches: The Unfiltered Truth of Life on the Road
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Thank you for tuning in and reading this. I super appreciate you.
~Karen
Oh yes, it is. We ended up staying just outside of Ocala which I’ll write about next. I can still feel the warmth and green.
Ocala is beautiful!