Monticello’s homes and historic streets tell the story of a small Southern town’s journey from an optimistic frontier settlement to the Civil War. On this walking tour, you’ll follow the true story of Mary Adeline Walker and her husband William (central characters in the *Palmetto Pioneers* book series) through Monticello’s remarkably preserved historic district. The tour begins at the Jefferson County Courthouse Circle, the political and social heart of 1840s Monticello, where citizens first learned Florida had achieved statehood in 1845. As you walk, you’ll discover how Jefferson County became one of Florida’s political centers and how its position as one of the state’s largest slave-holding counties influenced its swift support for secession. Throughout the journey, you’ll learn how Monticello’s early settlers, nicknamed “Palmetto Pioneers“ for their South Carolina origins, transformed a Florida frontier outpost into a thriving cotton-shipping town. The tour ends at William Budd’s general store on the courthouse square, now a popular local coffee shop where visitors can relax – just as townspeople once gathered to exchange news when the nation was moving toward conflict. Along the way, you’ll have a chance to: • Discover the site of Monticello’s first railroad depot, constructed in 1859 when the town’s wealthy citizens demanded a spur line to ship their cotton • See the antebellum home of Dr. Thomas Palmer, who served as the Walker family physician before becoming chief surgeon at a Confederate hospital in Richmond during the Civil War • Visit Jefferson Academy, Florida’s oldest brick school building, constructed by enslaved laborers in 1852 and still standing today • Explore the historically significant location of Monticello’s First Baptist Church, where Mary and William worshipped and community gatherings took place • See the impressive Greek Revival homes of William Budd and William Dilworth, local leaders whose families profoundly shaped the town’s development • Understand how Jefferson County’s position as one of Florida’s largest slave-holding counties influenced its swift support for secession and the Confederacy This 75-minute walking tour is based on meticulous historical research by the author of the *Palmetto Pioneers* series. It brings to life the true stories of people who witnessed Florida’s rapid transition from territory to state to Confederate stronghold, all within the span of a single generation.