Small Town Squares : Monticello, FL

Our #smalltownsquares series continues with a trip to a tiny town in Florida. Monticello has a special place in my heart. In Georgia, it is where Shane’s family has a beautiful farm, a place where we’ve made so many wondering memories over the years.

In Florida however, it is nearly as magical. A small, almost forgotten town just 20 minutes East of Tallahassee, where I grew up, Monticello has some of the most beautiful bones of a small town square.

Monticello, FL / heirloomed

The Courthouse sends in the center of town with roads weaving around it in all directions. The large Opera House is favorite of mine, filled with rows of seating and a grande stage packing the main room. You just wonder what kind of performances + occasions have taken place in this beautiful place over the years.

The town newspaper still operates out of a little brick building near the town square, otherwise lined with a small diner, real estate office and quite a few antique + second-hand shops (right up my alley). My oldest son enjoyed the Fried Shrimp on the menu at the diner, claiming them to be “his new favorite meal.”

Small Town Florida / heirloomed
Small Town Travel / heirloomed
Antiques / Heirloomed
Antique Mall / heirloomed

A boarded up jail is quite a sight to see, and the old school is currently under renovations. There are often folks parked near the square selling fresh fruits + vegetables from their roadside stands, and a bed + breakfast in a gorgeous old home.

The historic homes in Monticello are plenty. Many of them have seen much better days and need quite a bit of work, but from time to time I see a new one pop up and text it to my Mom in hopes she’ll take the risk. They are oh-so-charming and just filled with potential, especially as Tallahassee doesn’t have much in the way of historic properties remaining.

Old Home / heirloomed
Southern Homes / heirloomed
Small Town Travel / heirloomed

This grande old home was one of my favorites, I didn’t see it listed for sale but gosh I’d love to walk around inside and bring this beauty back to life.

Love to know if you’ve visited Monticello before and what memories you have of this sweet Southern town. #HEIRLOOMED




heirloomed is a lifestyle brand with a mission of "keeping heirlooms around for another generation." Our blog features stories about family recipes, creating traditions with your family, interior design and entertaining by mixing new and vintage pieces, classic style, and small town + historic travel. Our shop features a collection of "goods inspired by the past, for generations to enjoy" with an array of products and meaningful gifts including linen apronstabletop linensartceramics and beyond. Learn more at