Jefferson County in 60 Seconds

By: Gary McKechnie

Every county has at least one feature that makes it different from any other. In Jefferson County that something is something that’s missing. 

Try as you might, you won’t find a single traffic light in all of Jefferson County, Florida. Really. In a county that stretches from the Georgia border to the Gulf of Mexico (earning it the nickname “Keystone County”) their absence speaks volumes about the area’s rural nature.

So you may well find yourself asking what will you find in Jefferson County, Florida? 


Things Will Be Great When You’re Downtown

If you know even a little bit about history, you may recall that Thomas Jefferson passed away on July 4, 1826 -- the 50th anniversary of the signing of the Declaration of Independence. So several months later when Floridians sat down to form a new county, it must have been easy to name it in honor of our third president. That done, there was only one possible name for the county seat.


You’ll find it on Highway 90, 25 miles east of Tallahassee where, in the center of a roundabout (no stoplights here) the county courthouse features a Latin motto “Suum Cuique” (‘To Each His Own’) above its door. Here, as in many of north Florida’s rural counties, there’s a distinct Southern feeling that colors the heart of town.

West of the courthouse on U.S. 90, a smart first stop is the Monticello-Jefferson County Chamber of Commerce where you can find the aforementioned driving maps along with brochures and informative pamphlets for local sights and attractions. If the Chamber, which is inside a converted church, is closed, just pick up materials from a rack of brochures outside.

A short drive west you’ll see a memorial to the flag-raisers at Iwo Jima. While the image most recognize is Joe Rosenthal’s famous photograph, prior to that soldiers had raised a smaller flag in the same spot. One of those men was Ernest "Boots" Thomas, Jr., a 20-year-old who was raised in Monticello and, sadly, killed in action on March 3, 1945, just nine days after he helped plant the flag atop Mount Suribachi. In 1948, his body was returned to Monticello where he was buried at Roseland Cemetery.

Back by the courthouse, getting to know the town is easy. Walk in any direction where shops and restaurants radiate outward on each street. There’s an organic café and bakery, a Mexican restaurant, a pizza place, and an assortment of retail stores including some wonderful thrift stores and antique shops featuring an impressive assortment of items.

Then there’s Monticello’s famed Opera House. Built in 1890, this historic building remains a “rural center for the arts” with regular performances such as plays, touring musicians, holiday shows, and murder mysteries. The performance hall is upstairs, with downstairs space available for private parties and weddings.

The stately old courthouse in Monticello, in Jefferson County

The stately old courthouse in Monticello, in Jefferson County.

- Colin Hackley for VISIT FLORIDA

A few blocks east, just past a fabulously restored antebellum home that brings to mind Tara from “Gone with the Wind,” the Jefferson County Farmers Market is as colorful and delightful as any country market you’ve seen.

Before heading out, take a self-guided tour of the town (you’ll find maps at the Chamber). Monticello’s entire 27-square block historic district, which encompasses roughly 600 pre-1930s buildings, received its own listing on the National Register of Historic Places and within this group are 22 individual buildings also listed on the register including the the Jefferson County Jail and the Monticello High School. 

On the Road – and On the Waterfront

If you have your heart set on a country drive, Jefferson County is the right place. The county offers a map (again, at the Chamber) that charts four Heritage Road Drives that explore different sections of the county and, collectively, provide a better understanding of the region.

Since the county’s topography is a blend of river roads, farms, hills, flatland forests, and dirt roads, nearly every suggested drive will reveal a new and different look. With the help of historic markers and additional research, you’ll start to understand the timeline of the Native Americans, Spanish, British, and early settlers who came here to expand an empire or eke out a living through farming, timber, or ranching. The four trails include the Miccosukee-Magnolia Trail (northwest), the Plantation Trail (northeast), the Spanish Trace (central), and the Flatwoods-Wilderness Trail (southern).

Exploring Jefferson County will largely depend on your confidence in yourself, your maps, and your GPS. For instance, when viewed on a map sprawling Lake Miccosukee just north of Monticello seems as if it would be a natural for skiing and other water sports. It turns out the shores of this shallow lake are difficult to reach. If you do head out to find it, the roads will take you far, far into the countryside with only a handful of trails leading to the waterfront. That said, working your way toward the 6,312-acre prairie lake and surrounding wetlands may be worth the effort if you’re more inclined for fishing and duck hunting. Several miles west of Monticello, a boat ramp by the U.S. 90 bridge enters at a canal that leads to the lake. 

Likewise, the Aucilla River seems as if it would be perfect for a day of canoeing, but nature has reserved it for experienced canoeists. While some stretches can be navigated, the challenges are swift currents, man-made dams, shoals, swamps, and sinkholes that take the mysterious river underground, only to have it reappear again further downstream.

Perhaps the county’s most popular waterway is the Wacissa River. To reach it from Monticello, head west on US 90 and after crossing the bridge on the southern reaches of Lake Miccosukee (you’ll see the boat ramp) you’ll enter Leon County for a short stretch. Note that a side road can take you to the Letchworth-Love Indian Mounds Archaeological State Park where you can see Florida's tallest Native American ceremonial mound, built between 3,800 and 3,100 B.C. After the main highway re-enters Jefferson County, watch for Gamble Road (C.R. 59), which will take you for several long and lonely country miles south toward Wacissa. At the junction of highways 59 and 259, pass the Boland Country Store and a mile ahead is the Wacissa River. A small park at the water’s edge frames a picturesque scene of the land that time forgot.

There are towering cypress trees (some with rope swings attached) and islands of water hyacinths all framed by the bend of the broad, sparkling spring-fed Wacissa River. With the Wacissa River Paddling Trail flowing past and nearby liveries renting canoes and kayaks there’s every reason to take to the water. Stick with the waterway and you may reach the historic Slave Canal. To link the Wacissa and Aucilla rivers and move cotton to the coast, in the mid-1800s slaves were forced to dig the nearly five-mile waterway by hand. In time, trains ended up carrying the load so the canal was never completed, but rocks along the banks are a reminder of this tragic time. Overall, the waterway holds a bit of mystery with some tributaries that return to the main channel, some disappearing into the swamp, and long stretches that are surrounded by the jungle. 

From here, back roads lead to other small communities like Waukeenah, Capps, and Lloyd that, if only for the desire to see more off the beaten path Florida, are worth a visit. Eventually the roads lead to Lamont and a sight familiar to anyone who’s ever driven between Tallahassee and Gainesville on U.S. 27.

With its slipshod and rustic look that captures the essence of Old Florida, Robinson’s Pecan House is a roadside market that looks as if it had been constructed by vandals. But if you want pecans, country smoked sausage, hot boiled peanuts, cane syrup, grapefruit, sweet onions, Tupelo honey and mayhaw jelly, this is the place to find it.

Southern Cross

Even though Jefferson County spans the distance between Georgia and Gulf of Mexico, it doesn’t share the same white sand beaches of its Gulf Coast neighbors further west. Instead, much of the county’s southern region is part of the Aucilla Wildlife Management Area, a region seldom seen by any traveler.

It wasn’t always that way. After finding items such as burial mounds, middens, and spearheads used to kill mastodons, archaeologists have confirmed Native Americans were living in the vicinity of the Aucilla and Wacissa rivers 12,000 years ago. In more modern times, people were content to harvest old-growth cypress from the swamps. After obtaining 14,000 acres in 1988, Florida has added to the WMA with additional purchases that are being restored. Hunting for wild turkey, quail, wild hogs, and deer are popular activities.

Odds & Ends


With hills, canopy roads, and quiet country lanes, Jefferson County has some great routes for riding, including a portion of the Florida Sierra Club’s 100-mile Canopy Roads ride. Starting in Tallahassee, a 30-mile stretch crosses into Jefferson County, passing Wacissa Springs and going north to Wacissa Tower (the site of the old Spanish Missions of San Francisco de Oconi and La Conception de Ayubale) before reaching Monticello and returning to the state capital. 

Watermelon Festival

A Monticello tradition since 1949, this June event promises everything from pageants to parades, bed races and BBQ- and
small town fun for the entire family. Arts and crafts, food vendors, a golf tournament, a children's theater production, a classic car show, a street dance, and live music- plus a bunch of sweet watermelon- round out the attractions.

Dixie Plantation

In the northern edge of Jefferson County, this expansive property crosses over into neighboring Georgia – and crosses over several purposes including research, conservancy, equestrian events, and hunting. For some visitors, the highlight is the grand home designed by John Russell Pope in 1936 and completed in 1940. You may be familiar with some of Pope’s other works: the Jefferson Memorial, the National Archives, and the National Gallery of Art.

Avera-Clarke Bed & Breakfast

Located on a full acre near the heart of Monticello, this four-bedroom pet-friendly, eco-friendly inn blends modern touches with antebellum Florida. 

For more on Jefferson County, check out these Jefferson County Highlights.

Click here for An Itinerary for Adventure in Jefferson County, Fla.



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