SMALL TOWNS ROCK – MONTICELLO, FLORIDA

The centerpiece of Monticello, Florida, thirty miles east of Tallahassee, can be seen from all directions when approaching the downtown of the small town and county seat of Jefferson County. The two main highways into town converge at the Jefferson County Courthouse, which pays homage to our country’s third president.

The Classical Revival structure with French influences was constructed to loosely resemble Monticello, Virginia, the home of Thomas Jefferson. However, in true Old South tradition, the Florida version is pronounced with an “s” sound on the “cello” part. Traffic circles around the courthouse and joins US Highway 90—flowing east and west—with US Highway 19 heading north and south.

Thomas Jefferson died in 1826 one year before the county was formed. Some say the county and town were named to honor his contributions to the founding of the United States. But I found one historical account stating that several of his descendants resided in Jefferson County for many years.

When I first moved to Tallahassee eighteen years ago, Monticello was simply a name on a sign off I-10. But a few years ago, I rediscovered an old friend who lived in Thomasville, Georgia, fifty miles from my home. Monticello sits right smack dab in the middle of both our homes. For the past three years, we’ve been meeting in Monticello for lunch several times a year. We’ve not tired of the restaurants—which are plentiful—nor of the unique shops selling antiques, plants, Tupelo honey, and a multitude of other unique items.

Downtown Monticello

It’s a gem of a small town. Even though the population hovers around 2,500, the traffic around the courthouse circle shows a vibrant population of residents and visitors on any given day of the week.

Thick forests and rich soil drew the first settlers to the area. Cotton, corn, pecans, and watermelon dominated the economy for decades. During the Gilded Age years, 1865-1902, the wealth of the country changed dramatically as did the lives of its people. Immense fortunes brought folks to Florida’s warm climate, and places such as Monticello and Thomasville thrived.

During this boom time, the first passenger train brought tourists to Monticello in 1888. To help provide services for the influx of folks, wealthy businessman John Perkins built the Perkins Block in 1890. The ground floor held a general store and mercantile shop. The second floor became the Monticello Opera House where plays, vaudeville shows, touring opera companies, and even the circus entertained residents and visitors.

In 1909, across the way from the Perkins Block, the courthouse was constructed. The Latin phrase Suum Cuique is inscribed above its entrance doors. It means “To each his own,” but locals sometimes say it means, “Sue ‘em quick.” The structure dominates the town’s center.

The Perkins Block on the right with the courthouse right at the center of it all.

As happened with far too many small towns across the United States, several things conspired to end the boom in the first part of the twentieth century. A series of diseases killed much of the agricultural livelihood, which began the decline. The spiral toward the depression began. A fire destroyed the town’s largest hotel in 1917. And the death toll rang on Monticello in 1927 when it was decided to reroute the railroad through Lloyd, a small farming community west of Monticello. By then, the depression gripped the community, and the theater eventually closed its doors as did the other businesses housed there. It remained in disrepair until 1970, when private donations, fundraising efforts, and state grants sponsored a restoration project. Today, the theater provides year-round entertainment, and its courtyard is the site of many events, including weddings. It also draws people from Tallahassee and Thomasville, my friend and I included, to its downtown area with six or seven restaurants scattered within walking distance of one another.

To honor its agricultural past and present, each June the town holds a watermelon festival.

This year, the 74th Annual Monticello Watermelon Festival occurs on June 13 and 14, 2025. Click here to learn more.

Thank goodness for the resilience of the people of this country who honor the past and charm visitors with its ingenuity.

Leave a comment