For years, I have been driving Interstate 10 west to Tallahassee either as a student at Florida State University or the parent of two daughters at FSU. In all of those years, I rarely ventured off the main highway to visit any of the smaller towns. However, now that I have moved to Tallahassee, Monticello is becoming one of my favorite small Florida town.

First, let me say, the drive into Monticello on U.S. Highway 90 will more than likely be full of color in the coming month, as crepe myrtles lined both sides of the road. That in itself would be worth the drive, but there is much more to this charming town.

Jefferson County Courthouse

Monticello is the county seat of Jefferson County, named after Thomas Jefferson, the third President of the United States and author of the Declaration of Independence. If you know history, you might know Jefferson’s home in Virginia also bore the name Monticello. The town was named after that home and serves as the hub of the county. The Jefferson County Courthouse sits in the center of town and was built in 1909. The Latin phrase “Suum Cuique”, can be seen above its doors, meaning “to each his own” or “may all get their due.”

Walking and Driving Tour of Monticello

Monticello is known for its historic buildings. If you want to get a glimpse of them, all you have to do is to take a drive off the main highway through town and meander through the side streets.  In all, there are more than 600 buildings in the area that were built before 1920. A walking and driving tour has been established to lead visitors to 26 of those structures.

Make sure to stop at the Chamber of Commerce on the way in to pick up a brochure showing the route along with a brief history of those buildings.

The Avera-Clarke House was built in 1890 by state legislator Thomas L. Clarke.  It sits on the corner of U.S. 90 and Pine Street and now serves as a bed and breakfast. With its red shutters and white picket fence, the building itself seems to say “welcome home.”

Other homes in Monticello represent those typical of the Old South.

Monticello Opera House

One of the primary historic structures is The Monticello Opera House, built in 1890 by businessman John H. Perkins, in what is known as the Perkins Block. Sitting across from the courthouse, it still serves as a cultural and arts center for the area.  The second floor of the building houses the theatre itself, which is often said to have nearly perfect acoustics.  Local companies regularly put on musical and theatrical shows, as well as other musical groups. (Check the calendar of events for dates and times.)

Shopping and Other Activities in Monticello

We visited on a Sunday, and other than church activities, the streets of Monticello were relatively empty. The shops were closed, but the town still showed off its charm with antique stores, restaurants and other locally owned businesses.

 

As is the case with small towns, Monticello also lays claim to other activities. The second weekend in May is the Southern Music Rising Festival featuring musicians from all over the country. They set up in the Opera House and on the porches of the houses throughout downtown to entertain visitors with old time music. The town also comes to life during the third weekend in June with the Jefferson County Watermelon Festival.

And if you are into haunted ghost tours, Monticello is known as the “South’s Most Haunted Small Town.” Historic Monticello Ghost Tours are held through September and cemetery scavenger hunts are also offered through reservations.

Monticello is a small town with a big heart and a big history.  This trip definitely taught me a lesson: make it a point to get off the main highways and visit some of the smaller towns in the state. Those towns are where you will experience the “real Florida.”