Historic Jefferson County’s 25 Must-Do Ideas

Woman in a frame with historic courthouse in background
@JoGoesEverywhere uses the “selfie frame” at the Monticello Courthouse

There is one county in Florida that doesn’t have a single stoplight—Jefferson—my kind of place! By Florida standards, this historic county is quite old. When it was chartered in 1827, Florida was still a territory. The county was named for the country’s third president, Thomas Jefferson. The county seat, in honor of his Virginia home, Monticello (but townspeople are quick to tell you it is not pronounced that way!) The people are friendly, and the pace is easy with small-town values. Monticello is a lovely town with restored historic homes, set between giant live oaks; many pre-date the Civil War.

One of Jefferson County’s tag lines is “Where History Welcomes Tomorrow.” I can tell you this is true! Everywhere I went, there was excitement about new businesses coming to town, not complaints about competition. Many new companies are making themselves at home repurposing old buildings (even the Chamber of Commerce is in a renovated church.) Kelly & Kelly Properties found a home in a service station (and hosted an “After Hours” Chamber event that I managed to crash!) And instead of lamenting the change that comes with technology, the community has embraced it and put up a “selfie frame” to showcase their historic Courthouse.

The roots of community spirit run deep. In the 1930s, local nursery owner Fred Mahan provided more than 35,000 ornamental plants, mostly Crepe Myrtles, to beautify the highway from Monticello to Tallahassee.

1. Stay in a Historic House

The Avera-Clarke House Bed & Breakfast was built in 1890 by Thomas Clarke. Clarke was a delegate to Florida’s Constitutional Convention in 1885. His son, Judge Scott Dilworth Clarke, and his family lived in the house. There are beautifully-appointed rooms in the main house. There is also a separate ADA-approved guest house (not a “cottage”—I could move into this place and be quite happy!) The 1.5-acre grounds are beautifully landscaped.

Historic two-story yellow home

2. Tour a Research Institute

The Aucilla Research Institute has an extensive collection of fossils. The Institute performs original earth science and natural history research in the prehistoric and historical past of the Big Bend region. The Aucilla Institute offers incredible opportunities for researchers and students to conduct paleontological, archaeological, geographical, topographical, and ecological fieldwork throughout the area.

I know this sounds pretty advanced and maybe too “scientific” for the average Jo (pun intended!), but this is what it really means:  These folks have proven that the first Americans had a settlement and were hunting big game in Florida 14,500 years ago! That is more than 1,500 years earlier than initially documented. Talk about historic! And they have even discovered a mastodon tusk marked by a human-made tool! Wow!

a jawbone with teeth
A prehistoric jawbone

The facility has a collection of Native American arrowheads and points and has established a Virtual Museum. It is still under construction, but you can see the additions as they add to it.

3. Tour the Wirick-Simmons House

The entrance to historic Wirick-Simmons House - 2 story white building
Wirick-Simmons House

This Greek Revival house (one of a very few in Florida) was built in 1831 by a circuit-riding Methodist minister and has been restored to its former beauty. The Jefferson County Historical Association uses the house as their home base. The group is dedicated to preserving and responsibly using the historical treasures found in Jefferson County. The group hosts a bi-annual Tour of Homes, and the garden and lawn are available for receptions.

4. Stop and Admire a Church

One of Florida’s prettiest Carpenter Gothic churches is Monticello’s Historic District. Carpenter Gothic is an architectural style that involves taking architectural details originally carved by stonemasons and recreating them in wood. The technique uses the skills of local materials, building designers, and carpenters. Christ Episcopal Church on North Cherry Street, built in 1885, is one of those churches. One of the distinctive features of this style is narrow windows and doors with a Gothic-style pointed arch at the top, making it resemble a lance. There are two original stained-glass windows made in England. They are memorial windows donated by the families of devoted churchwomen. Over eighty of these churches were built in Florida between 1870 and 1900. More than 30 remain, mainly in North Florida.

Gothic style church
Christ Episcopal Church

5. Enjoy Shopping While You Wait for Your Lunch

At Tupelo’s Bakery, you can order your lunch and then peruse the store for crafts, and bee-utiful bee-related items, including beekeeping gear. The food is created from local and organic ingredients. There is a daily “Tupelo’s Famous Quiche” – but you’d better get there EARLY if you want that! Or you can order online to reserve your slice! The Hippie Chick Salad Plate is a delicious concoction that includes dried cranberries and toasted pecans.

glass case filled with dessert choices, woman owner leaning on top of the case
Tummy space is limited – select dessert first!

6. Make New Friends

At the North Florida Wildlife Center, you will make friends with various birds and animals. A behind-the-scenes tour was a fantastic way to spend the afternoon. And the lemurs were such little imps! One kept grabbing the camera to take a look–I guess he wanted to make sure I was capturing his best side! He didn’t need to worry—he was so cute there was no such thing as a “bad shot.”

Lemur looking at my GoPro as if checking his picture
How did my picture turn out?

7. Lights, Camera, ACTION!

Visit the Monticello Opera House, built-in 1890. It is located in sight of the Courthouse. In the front office, highlighted by cast iron and stained glass storefront, you will find memorabilia from the past 130 years. Be sure to inspect the original seat—you’re in for a surprise! With luck, you’ll be able to attend one of the musical or theatrical productions or musical group performances and enjoy the acoustically-perfect second-floor theater. Catered dinners are usually a part of the evening. So dinner and a play—who could ask for more? Upcoming 2022 shows include The Scarlet LetterWait Until Dark and a Murder Mystery Dinner Theater.

View from the stage of the Opera House seats
Opera House seats viewed from the stage

8. Visit Historic Plantations

Visit the plantations of the past in Jefferson County. More than 90,000 acres account for just the 12 largest plantations in the area! Conservation measures will ensure that these lands will never be developed. Many are now used for hunting. The hunting is done on horseback or from the comfort of a horse-drawn rack. Plantation employees serve as guides and dog handlers. Lunch is brought to the field at noon in insulated coolers and bags, and the main course is cooked in the woods.

9. Become a Porch-Sitter

At The Porch on The Green, you can sit on the front porch of a house that was built in 1922 and restored in 2006. Enjoy the evening breeze while you enjoy your dinner. The fried mozzarella is lightly fried, drizzled with balsamic glaze, and served over marinara. Yum! The soups selection varies daily, and there is an entree selection on the specials list. I was lucky and their fantastic Bourbon Glazed Salmon was available. I now understand the saying about something being “so good you want to slap yo Mama!” Oh my goodness! My host ordered the Caprese Chicken Pesto (and perfect host that she was, she shared!) It was another fabulous dish!

10. Spend the Morning With Aunt Louise

Louise may not be your aunt, but you will be family after visiting her farm! Aunt Louise’s Farm is fun, and you can learn a lot too! Check the calendar on their website before you make your plans. Monticello received an award in 1999—“Outstanding Rural Community of the Year.” This heritage is evidenced by the county’s largest employer—a plant nursery! Farms like Aunt Louise’s continue to share that rural heritage with today’s youngsters, teaching them to treasure those historical traditions.

Woman sitting in a feed tub filled with corn kernals
This is how the Director of Tourism unwinds!
man driving red tractor, pulling a sided trailer full of happy kids
Enjoy a hayride during your visit
  • Get lost in the 2.5-acre corn maze, filled with scarecrows and funny signs
  • In the Spring, that field is filled with wildflowers
  • Sit in a giant cattle feed tub filled with corn kernels
  • Meet the farm animals:  goats, sheep, miniature cows and horses, ducks, turkeys, peacocks, baby bunnies, and alpacas
  • Ride the barrel train
  • Bring your lunch and make use of the picnic tables

11. Earthen Mound

The Letchworth-Love Mounds Archaeological State Park is the largest earthen mound built by Native Americans in the southeast. Artifacts and evidence date this area nearly 12,000 years of human habitation. When you see a place like this and think about the numbers, all you can do is shake your head in wonder!

12. Local Art

The Jefferson Arts Gallery is housed in an old school building. There is a gallery, studios for artists, and classroom space. The exhibits change monthly, and there is a reception on the first or second Saturday.

13. 5 Rivers Adventures

Have you ever wanted to fly down a river or a swamp? On an airboat? Then 5 Rivers Adventures has got you covered! Captain Bradley and Captain Jon are Florida natives who grew up on the rivers and springs they now share with their clients. A day on the beautiful Wacissa or Aucilla River will be fun and educational. Both men love the area and are knowledgeable about the wildlife and the natives who once lived here. They know where the hidden springs are and are always quick to detour, so you have a chance to see everything. Twelve springs feed the Wacissa, and trust me—Captain Jon knew where to find every one of them!

View of a river, lined on both sides by cypress trees
A beautiful day for an airboat ride on the Wacissa River

14. Mini Moo (and) Alpaca Too!

What a great name, right? I mean, can you think of a better name for a farm? Go ahead…I’ll wait. They raise miniature cows, and they also have alpacas. At Mini Moo, you will be visiting a 6th generation farm. They are found in the Waukeenah community and raise miniature cattle, sheep, camelids (alpaca & llamas) and goats. They have special events, yoga weekends, and basically, the whole place is a petting zoo!

15. Circle the Square

The historic town square is a busy spot. They have cute shops and eateries in old buildings, and there is a “selfie frame” for a picture of you with the county’s Courthouse in the background.

The Old Jail is being restored, and tours can be arranged. You will also see the Monticello News building from 1859. Back then, an annual subscription to the local paper was $2.

The Monticello Historic District is a 27-block area, but there were nearly 600 buildings constructed before 1930, so there is plenty to see and admire!

There is a walking & driving tour of Historic Jefferson County that includes the town of Monticello, the district of Lloyd, and African-American historic sites. The brochure or download is available from the Chamber of Commerce.

16. Jefferson County Courthouse

Intricate tile mosaic floor in historic court house entryway

Don’t just settle for a photo of the building. The doors are open, so go on in. Built in 1909, the tile flooring is beautiful, and the walls are filled with historic photos. People working in the offices are friendly and happy to answer questions about the building and the area. The Courthouse is a focal point of Monticello, encircled by a round-about. There is a dome and clock on top, and porticos centered on the four sides. And don’t forget to take a selfie in the frame across the street!

17. Stop by the Depot

Train depots always evoke nostalgia; I suppose because we (I!) have a deep-rooted case of wanderlust. In the community of Lloyd, you can visit the oldest brick railroad station in Florida. The station was built in 1858. Just think what history those walls have seen in 164 years! It is now used by the U. S. Postal Service, so go in and mail a postcard from your visit.

18. Wildlife Watch

View of the Wacissa River with blue skies
The Wacissa River

The Wacissa Wildlife Management Area is more than 89,000 acres of unspoiled land, open to the public for hunting, hiking, and camping. It is bordered by the Aucilla River, one of the state’s richest archaeological areas, and the Wacissa River, which begins from two springs here in this area. These two pristine rivers provide fishing, boating, canoeing, and kayaking.

St. Marks National Wildlife Refuge consists of more than 70,000 acres along the Gulf coast, straddling the county lines of Jefferson, Taylor, and Wakulla. It is a prime area for migratory birds to spend the winter, and the miles of trails through the refuge lead to viewing locations.

19. Slow Down and Enjoy Nature

The Monticello Ecological Park is the perfect place to soak up nature. The three-quarter-mile loop trail weaves through tall pines and hardwood trees, which provide a home for a fantastic variety of birds. The elevated boardwalk is the perfect spot for viewing a spring-fed stream below. Exercise stations are located along the trail for the over-achievers among you.

20. Hit the Dusty Trail

Jefferson County has four different Heritage Roads that offer more than just beautifully canopied roads (although they certainly provide those too!) The county is known for its timber, rolling hills, and farmland. Pick the route that best suits the time you have for the drive: as little as 45 minutes up to 2.5 hours, pack a picnic to enjoy on a riverbank, top off your tank, and hit the trail through the naturally beautiful old South. Make a day of it.

Please stop by the kiosk at the Chamber of Commerce for a copy of the map or download it here.

21. Spin Your Wheels

Jefferson County is a little-known gem for the cyclist. There is a 1.5-mile Ike Anderson Bike trail running north-south through the center of Monticello over an abandoned railroad. (Railroad workers slipped in under cover of darkness and removed the rails! True story!!) There are also bike routes for a 30-mile ride, a 60-mile ride, and (gasp!) a 100-mile ride! For all the facts, call the Chamber of Commerce. More information is also on the Trail Link website.

22. Pay Your Respects

One of America’s heroes raised the flag at Iwo Jima. Monticello native, Platoon Sergeant Ernest “Boots” Thomas, Jr., was a 20-year-old Marine when he carried that first flag up Mount Suribachi. He was killed in action on March 3, 1945, only nine days later. His body was returned to Monticello in 1948 and interred at Roseland Cemetery.

Iwo Jima monument
Iwo Jima monument listing names of first Marines who raised the flag

23. Keep Up With the Joneses

Spend some time with Kim and Angela Jones at Florida Georgia Citrus. They grow it, pack it, juice it, and ship it! You can’t get a Satsuma orange any fresher than picking it right off the tree. And to be sure you take home oranges that won’t spoil, follow my lead and bring home their Satsuma Syrup! Mixed with olive oil and vinegar you’ll have a salad dressing in under a minute. But you can pour it over pancakes, or even drizzle it on cheese and crackers. Don’t worry—they give you a card filled with recipe ideas! While you’re there, pick up some bottles of frozen Satsuma juice, too!

24. One Last Stop

I was told, “Before you leave town you have GOT to go to Johnston’s Meat Market and get doughnuts. And go early before they run out!” I’m not known for following orders, but this time I did exactly as instructed. I’m so glad I did! I had good intentions of taking it with me on the road. Yes, that’s the steering wheel and the road in the background. Well…you know what they say about the road and good intentions. *sigh*

creme filled chocolate iced doughnut being eaten in the car
Creme-filled chocolate-iced doughnuts have a short life!

25. Festivals

As the saying goes, pick your poison. All you have to do is choose a month (or a topic), and Jefferson County probably celebrates it!

In February, test your skills (luck?) at the Poker Tournament. March? Tour historic homes. In April, Monticello has their annual Bike Festival before it heats up.

The Jefferson County Watermelon Festival is held annually on the third weekend in June. Not only is there a seed spitting contest, but there is also a parade, arts, crafts, food vendors, a classic car show, and a bed race! What fun! The festival began in 1949, so they are closing in on their diamond anniversary. Knowing this town, I’ll bet they have some fabulous things planned!

Naturally, the Fourth of July calls for a dazzling display of fireworks. August sees a Texas Hold ’Em tournament fundraiser for the building fund. In September, the annual Flea Across Florida event stretches from coast to coast along Highway 90. What a fabulous way to antique and junk hunt!

In October, they double down and have both historic ghost tours and a haunted Main Street. November celebrates the best of BBQ competition, a car show, and a Chili Challenge. Eat all you can hold, meet celebrity judges, and enjoy the music.

December wraps up the season with Christmas Around-the-Downtown, Bethlehem in Monticello, and finally, a New Year’s Eve Gala to ring in the new year.

More information on Jefferson County, things to do, and festivals can be found on the Chamber of Commerce website or the Visit Jefferson site.

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