Located in the vicinity an old Indian village, the town of Monticello was originally known as Robinson after its first postmaster, John G. Robinson. In 1827, the community changed its name to Monticello in honor of Thomas Jefferson's Virginia plantation, using a slight variation in pronunciation. Jefferson's agrarian vision for America took root in the fields around Monticello.

Before the Civil War, the town housed one of the state's three cotton mills and was the center of Florida cotton production. In 1851, construction began on an updated mill, augmenting wood with brick and tin to reduce the threat of fire that had destroyed another mill in the nearby town of Madison. During the Civil War, the new mill survived by manufacturing wool and cotton into yarn and cloth for the Confederacy. In the years following the war, however, the mill ceased production.

In order to regain statehood for Florida following the South's defeat, state legislators met in Monticello to ratify a new state constitution compatible with that of the United States. This document, known as the "Monticello Constitution," was the foundation for Florida's new government.

Cotton production, already in decline in the post-bellum period, fell drastically after boll weevil infestation of 1916. Forced to diversify, Monticello residents turned to lumber, vegetable crops, dairy farms, and nurseries, all of which were negatively impacted by the economic meltdown of the 1930s. With the inception of World War II and the end of the Great Depression, local farmers increased agricultural production to meet the food needs of a nation at war.

As late as the 1940s, Jefferson County produced 80 percent of the world's watermelon seed, a legacy commemorated each June in the Jefferson County Watermelon Festival. The festival is but one of many reasons to visit Monticello. Historic buildings dot the town and the surrounding area. The Monticello Historic District, with its nineteen structures, like the Perkins Opera House, is the center of the community's social and cultural activities. Just outside of town, the antebellum Lyndhurst Plantation stands as testament to the area's agrarian past and Jeffersonian legacy.

This podcast made possible through a grant from the Florida Humanities Council. Script written by Paul Zielinski. Narrated by Dave Dunwoody.