Outside Tallahassee Is Florida's 'Friendliest Small Town' Full Of Artsy Fun, Cafes, And A Vibrant Downtown

There is a small town in Florida's panhandle, just 17 miles from Tallahassee, with a rich Cuban heritage and artsy vibes. When one thinks of Havana, images of Cuban cigars and sugar cane fields may come to mind. Similarly, the town of Havana, Florida was once a thriving agricultural hub for tobacco during its earlier days. With a population of roughly 2,300 residents, this sleepy city's once-booming tobacco industry has given way to the vintage shops and antique stores that now line its streets.

Traveling through northern Florida, one can appreciate the natural beauty and historic charm of cities near Tallahassee, like Chipley. Located between the Georgia state line and the underrated college city of Tallahassee, Havana's proximity to U.S. Highway 27 makes it an ideal destination for a day trip in the Panhandle or a quiet stop on a road trip through the South. The town has walkable, pedestrian-friendly streets filled with vintage furniture stores and quaint cafes, as well as a thriving antiques and arts scene.

Havana is a tight-knit community of farms, residences, and local businesses, each infusing their own local flavor into this lesser-known town. Downtown Havana's Main Street bustles with unique shops and gorgeous public spaces that enhance its hometown feel, while holiday festivals set the town ablaze with festive cheer. October welcomes Pumpkinfest, a family-friendly celebration filled with fun activities, delicious refreshments, and live music. Wintertime visitors can look forward to a tree-lighting ceremony and WinterFest celebrations along Main Street.

Nicknamed Florida's "Friendliest Small Town," Havana was established in 1906 as a popular agricultural hub during the tobacco trade era. Considering Havana's bustling hand-rolled cigar industry, it makes sense that the town was named after the Cuban capital famous for cigar manufacturing. Travelers can visit the Havana History and Heritage Society Shade Tobacco Museum to learn more about the town's origins and how this crop contributed to the livelihood of Cuban immigrants in the area. The museum is housed in the original Planters Exchange structure, built in 1928 and once used by tobacco farmers during the industry's heyday. Inside, you'll see old photographs and paintings of tobacco fields, farming artifacts from the era, and various cigar displays throughout the building. Miniature models of tobacco barns encased in glass and murals adorn the space, offering a fascinating glimpse into the town's early agricultural history.

Like Dade City, a hub for antique shopping, dining, and family fun, Havana's downtown district is full of quirky boutiques. Make sure to look for the vibrant murals around town that highlight Havana's artistic flair and Americana roots. You'll see colorful artwork depicting the town's moniker, as well as tributes to old businesses such as the Havana Motor Company, featuring a vintage Ford truck and classic yellow school bus. Among the standout shops is Bernard's Hidden Treasures, which houses a unique array of vases and statuettes. The Havana Herald, a vintage printing shop, is filled with typesetting equipment and office supplies. You can also stop by Coon Bottom Farms Country Store for a glimpse of the town's past, with vintage printers and old town records available to browse.

The friendly town of Havana offers its residents peaceful surroundings and a serene way of life. With a lovely mix of antique shops and quaint cafes, all within close proximity to Tallahassee, it's perfect for those who want a taste of vintage Florida with big-city amenities nearby. A must-see antique shop is Weekend Finds Antiques & Gifts, located on Havana's Main Street. Part of the Florida Antique Trail, this curious boutique is stocked with classic wooden furniture, beautiful embroidered textiles, and charming handmade gifts. 

Havana has a thriving artists' community, bolstered by initiatives such as Artists Helping Artists, which supports creatives by showcasing their works and exhibits. The 2,000-square-foot Artists Helping Artists Gallery features a wide range of locally-made pieces, including wooden sculptures, pottery, paintings, jewelry, and much more. Also worth visiting is the D. Arthur McBride Portrait Studio and Gallery, which features an impressive collection of oil paintings depicting natural landscapes, wildlife, and life-like portraits. 

After exploring Havana's vibrant galleries and boutiques, stop at Poppy's Coffee & More for an afternoon pick-me-up. You'll find fragrant coffee blends from all over the world in this charming cafe, along with delicious treats. Rooster's Roasters is another adorable coffee shop a few doors down, featuring fresh roasted coffee and homemade baked goods. After your coffee fix, visit 850 Cigar Lounge to get a taste of what Havana is all about. Visitors can enjoy an array of quality cigars just down the road from both cafes.