The Palmetto Pioneers: A Monticello Walking Tour
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About the Tour
About the Tour
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.
Tour Producer
Tour Producer
Cindy Roe Littlejohn
Cindy Roe Littlejohn is an author of historical narrative nonfiction books and the series “Palmetto Pioneers.” Her territorial Florida adventure, “Palmetto Pioneers: the Emigrants” and its sequel “From Harmony to Hostility” have received critical acclaim. Her debut book in her “Palmetto Pioneers” series won a bronze medal at the IPPY Awards for nonfiction in the southeast and two gold medals for history and biography, and a silver for cover design from the 2024 Florida Authors and Publishers Association awards. The second book was a finalist for an IPPY award and won a bronze from FAPA.
She has a ph.d. In Communication from Florida State University, is on the executive committee of the Florida Historic Old Capitol, and sits on the board of the Jefferson County Historical Association. She is considered a local and state historian and is an Associate Scholar for the Aucilla Research Institute.
She published the first book in the series "The Emigrants" in the summer of 2022. On March 15, 2024, she released her second novel in the series, "From Harmony to Hostility," which follows the Walker family into the Civil War. Her third book in the series “Yankees in the Courthouse” was released at the end of 2025.
She comes from a small rural town in North Florida and is the eighth generation of her family to have lived there.
Preview Location
Preview Location
Location 17
Old Monticello Jail & Hanging Tree
To your left is where they built Monticello's first substantial jail. In the book, it is the jail run by William, who became sheriff in 1855. We are passing the back of the jail. A tall log fence kept prisoners in and the public out. The fence made it look li... Read More
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Major Landmarks
Major Landmarks
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Courthouse Circle
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Monticello Historic Main Street
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First Presbyterian Church
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Christ Episcopal Church
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CowHaus Coffee Company
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Monticello Jefferson County Chamber of Commerce
Getting There
Getting There
Route Overview
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Start locationUS-90, Monticello, FL 32344, USA
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Total distance3km
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Final location90-190 US-19, Monticello, FL 32344, USA
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Distance back to start location76.27m
Directions to Starting Point
The tour begins at the intersection of Washington Street (US 90) and Jefferson Street (US 19) in the courthouse square public parking lot, whose entrance is at 185 Walnut Street.
Show Directions
Tips
Tips
Places to stop along the way
If you are in the mood for a sit-down meal, several very good restaurants are within a few blocks of the tour. The Social Monticello is at the northeast corner and Rev Cafe is at the southeast corner of the Courthouse Square. The Porch on the Green is two blocks east of the Railroad Spur/Walking Trail on East Washington Street. Jackie's Brickhouse Eatery is one block north of the Courthouse Square on North Jefferson. Rancho Grande is one block west of the intersection of Pearl and Waukeenah Streets. Tupelos Bakery is two blocks east of the intersection of West Washington and Water Streets. VJ's Florida Bar & Grill is located on South Jefferson and Papa & Nonni's is on North Jefferson. The latter two restaurants, though, are many blocks off the tour but can be reached by car. For coffee, may I suggest the Cowhaus Coffee Company, which is the last stop on the tour. For a refreshing drink, such as their Watermelon Cooler, check out Groove Nutrition, which is a half block west of the Cowhaus on the Courthouse Square. For homemade gourmet doughnuts, check out Glazed Over on North Cherry Street, just north of The Social. You can find a full bar at either The Social, Rev Cafe, Rancho Grande, or The Porch on the Green.
Best time of day
Anytime during daylight hours, but if it is summer, try to do it early in the morning or very late in the afternoon.
Precautions
Monticello is a safe city for walking, but be aware that some of this tour briefly enters an industrial area. Remember that Monticello is a working-class small town. Bring along a bottle of water, sunblock, sunglasses, and possibly an umbrella. Florida gets an average of 60 inches of rain a year. If it is winter, realize that North Florida enjoys four seasons, so a jacket may be needed. It snowed a couple of inches in town last January, though this was very unusual.
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