Savor & Stroll: A Historic Walking Tour of Downtown Kissimmee

Start your tour by paying tribute to Bette Sprinkle, affectionately known as the “First Lady of Osceola County.” Next to the intersection of Broadway and West Darlington Avenue, you’ll find a statue of one of  Downtown Kissimmee's most beloved figures, Bette Sprinkle. For 25 years, Sprinkle played a vital role in shaping the community, leading the Downtown Business Association and launching the city’s very first farmers market.

After her passing in 2004, a bronze statue was erected to honor Sprinkle’s contributions to the area. Located outside her former drapery store, now Aviles Hair Salon, the statue reflects her impeccable style and community pride. If you look closely, you’ll find a butterfly on the back of the statue, symbolizing Sprinkle’s free spirit and commitment to beautifying the downtown she called home. Today, her niece runs the drapery store on Darlington Avenue, proudly continuing the family tradition in the heart of Kissimmee.

After taking in some local history, it’s time for a delicious treat! Just a short stroll across West Darlington Avenue, you’ll find La Ro Café, a local favorite for Venezuelan pastries and coffee. This cozy café blends long-standing family recipes with a passion for quality, making it a must-visit on your tour.

For a quick snack, try their savory cachito, a ham-and-cheese pastry ideal for on-the-go. Pair it with their caramel iced coffee to fuel up for the rest of your adventure. And if you’re craving something sweet, don’t miss their signature Milhojas — a flaky pastry with creamy layers that are "just like Nonnita used to make."

Walking north on Broadway, you can’t miss the signs of Kissimmee’s rich cattle heritage. From the symbols on the lamp posts to the details on the sidewalks, it’s everywhere you look! But if you really want to feel the town's history, head north to the corner of East Dakin Avenue. Keep an eye out for the iconic giant horse sign—there, you’ll find a building still marked "Hardware," a nod to its past as the legendary Makinson Hardware, now transformed into the vibrant 1881 Restaurant & Bar.

The Legacy of Makinson Hardware

Makinson Hardware’s story began in 1881 when the first business charter was signed, setting the foundation for a legacy that would last nearly 140 years. Over time, this beloved store became Florida’s oldest operating hardware store until its closure. But Makinson Hardware was more than just a place to buy tools and get your lawnmower repaired. It was a community hub where locals knew each other by name and kept running tabs (paid only once a month!). Farmers, fishermen, and cowboys alike relied on this store for essential supplies, making it a cornerstone of Kissimmee’s history.

A Taste of the Past at 1881 Restaurant & Bar

Although Makinson Hardware closed in 2021, its legacy lives on through 1881 Restaurant & Bar. The new establishment preserves the historic charm of the building, with its vintage brick and nostalgic photos of Kissimmee’s past adorning the interior, all donated and curated by the Makinson family and the current owners, the Parsons Family. Step outside, and you’ll discover a stunning mural featuring Kissimmee locals from yesteryear as you relax by the bar.

Take on the Gold Buckle Hamburger, a monster burger served with bacon, jalapenos, and caramelized onions that will have you feeling like a real cowboy. Then, saddle up for dessert with the Bette Sprinkle Sundae, a warm skillet cookie topped with vanilla ice cream and a cherry. And now that you’re officially in the loop after checking out the Bette Sprinkle statue, you can enjoy this sweet treat like a true local insider!

Continue your walk down East Dakin Avenue toward the corner of Lakeview Drive and East Monument Avenue, where you'll find Kissimmee’s most beloved landmark: the Monument of States. Towering 50 feet, this colorful structure was finished in 1943 thanks to the visionary efforts of Dr. Charles Bressler-Pettis. During World War II, he wanted to create a powerful symbol of national unity, so he reached out to governors across all 50 states, asking them to contribute a rock or stone native to their state.

The result is an eclectic monument of more than 1,500 stones from 48 states and 21 countries! Each piece represents the country's unity during a war, and walking around it today offers a fun glimpse into Kissimmee’s unique patriotic spirit. Look for rocks engraved with state names. Can you spot yours?

Finish your walking tour with a refreshing treat at Ruby Plaza Café. Indulge in limbhelados — Puerto Rican-inspired frozen treats made with fresh fruit and top-quality ingredients. Tucked away at the intersection of Ruby Avenue and Lakeview Drive, this local favorite is known for its scrumptious snacks and frozen desserts. After over 20 years of perfecting his recipe, the café’s owner brings the flavors of the Caribbean to life in every bite.

For a tropical delight, try the coconut limbhelado, packed with chunks of fresh coconut. Or, if you're a certified chocoholic, the Nutella bizcochados is a decadent choice — rich ice cream layered with Puerto Rican sponge cake and dusted with hazelnuts. Savor each bite by kicking back and soaking in the gorgeous views of Lake Tohopekaliga nearby. After a fun-filled walking tour, you deserve to indulge in these sweet treats!