Monticello, Florida


A crowd gathered around the courthouse for a speech (1945)

Monticello is located in the heart of Jefferson County in the rural panhandle of northern Florida.  Officially incorporated in 1831, it continues to serve as the county’s seat of government. The county courthouse stands in the center of town at the convergence of its two main roads – Washington (Highway 90) running east and west, and Jefferson (Highway 19), running north and south.  Today, Monticello is home to nearly 2,500 people who take pride in its “small town charm.”  Early settlers found the region’s thick forests and rich soil an ideal place to live, and many of their descendants remain there to this day. 


Laborers loading watermelons into a seeding machine (1946)

Agriculture is the most important industry in Monticello’s history.  As one Florida Union Times writer put it, “The farm products of this land of hills, and vales, brooks, rivulets and rills are the material essence of life to the town.”  Cotton, corn, pecans, and especially watermelons, were the city’s most abundant crops.


A portrait of "Mauma" Mollie (ca 1855)

As a farming community, enslaved laborers were vital to the region’s development.  Men and women worked from dawn to sundown clearing trees, digging ditches, plowing fields, and sowing crops.  Children also carried out small tasks in the field as well as the main house. Although the law required a white supervisor to be present at all times, some enslaved men even served as overseers and managed the daily tasks on the plantation.

Plantations owners also depended on women like “Mauma” Mollie to cook and help care for their families.  In 1873, Jefferson resident Henry Edward Partridge remembered his nurse Mollie, “in whose cabin we had often eaten the homely meal of fried bacon & ash cake and where we always had welcome and sympathy and whom we loved as a second mother.”


The Monticello Opera House (2012)

The Monticello Opera House is a testament to the city’s vibrant past..  In October 1888, the first passenger train arrived in Monticello, opening up a floodgate for northern tourists.  They were eager to escape the harsh cold and explore the hunting and fishing opportunities in northern Florida.  In 1890, businessman John H. Perkins built the “Perkins Block,” a large brick structure that included a general store and mercantile shop on the ground floor and a theater on the top floor.  Depending on the event, guests could pay twenty-five to seventy-five cents to see drama, listen to live music, or marvel at the circus.

Over the next few decades, the tourism industry began to wane.  Business for the opera house slowed and eventually halted.  The building closed and remained in disrepair until the 1970s, when local citizens formed The Monticello Opera Company and restored the site to its former glory.  They now have a regular schedule of events by local and guest performers.


Monticello High School senior class of 1930

The end of the Civil War brought the development of a public school system that provided education to every child, regardless of social status.  By 1890, sixty-five schools operated in Jefferson County – thirty were designated for white students and thirty-five for black students.  In 1851, Jefferson County High School (seen in the background of this picture) was the first brick school building in Florida.  It enrolled white students only until county officials finally desegregated the school system in 1965.


St. Elmo Hotel (19--)

Built in the 1890s, the St. Elmo Hotel was one of many guesthouses eagerly welcoming visitors to Monticello.  Early twentieth century tourists found greater independence through their family automobiles and flocked by the thousands to Florida’s sunny coast.  Automobiles also meant greater mobility for Monticello residents, and many sought entertainment and employment outside the city.  This was in part due to Jefferson County’s economic decline that began when various diseases wreaked havoc on farmers’ crops and livestock.  Florida’s “land bust” in 1925 and the nation’s descent into depression did nothing to improve conditions.  In 1927, the railroads also chose to bypass the city and discontinued passenger services, severely damaging tourism and trade.  The St. Elmo closed after a fire in 1917, and many other hotels struggled to stay open as the century progressed. Despite some economic recovery over the decades, Monticello was never the same.


"Boots" Thomas and members of the forty-man patrol planting the first American flag at Iwo Jima

From the Civil War, through both world wars, to the continuing “War on Terror,” citizens of Monticello and throughout the county have served in their country’s armed forces.  On February 23, 1945, Monticello native Platoon Sargent Ernest “Boots” Thomas, Jr. helped lead a forty-man company of U.S. Marines to the top of Mount Suribachi on the island of Iwo Jima.  He with four others raised the first American flag on Japanese soil.  (The second flag-raising was immortalized by photographer Joe Rosenthal and became the inspiration for the Marine Corps War Memorial outside Arlington Cemetery.)   Thomas was killed by enemy fire a few weeks later.  He was awarded the Navy Cross and was buried in Jefferson County.


Children holding watermelon slices at the annual Watermelon Festival

Since 1950, Monticello residents come together every summer to celebrate the Jefferson County Watermelon Festival.  The county was once considered the greatest watermelon seed producer in the world.  Today’s residents enjoy celebrating their heritage as the highlight of the year.  Special events include community dinners, a parade, arts and craft shows, a street dance, a five-kilometer race, and of course, plenty of watermelons.

Monticello, Florida