23 Best & Fun Things To Do in Monticello (FL)

Monticello is a small city located in Jefferson County, Florida. It serves as the county seat and is part of the Tallahassee metropolitan area. Monticello is known for its rich history and is named after Thomas Jefferson’s famous estate. The population is about 2,589, making it a close-knit community.

Monticello sits in northern Florida. It is well-connected by U.S. Route 90 and U.S. Route 19, making it accessible from nearby Tallahassee. The city covers about 4 square miles of land and enjoys a humid subtropical climate, with hot summers and mild winters.

One of Monticello’s unique features is its historic sites. The Jefferson County Courthouse, modeled after Monticello (Jefferson’s estate), sits at the city center. Other attractions include the Perkins Opera House and Monticello Old Jail Museum. Letchworth Mounds, one of the state’s most significant Native American archaeological sites, is located nearby.

Monticello is also famous for holding Florida’s record-high temperature of 109°F in 1931. The city’s charm lies in its historic character, warm climate, and small-town atmosphere, making it a notable spot in northern Florida.

Are you planning to visit Monticello? Here are the best things to do in Monticello, FL.

Things To Do in Monticello, FL

1. Visit the Jefferson County Courthouse

The Jefferson County Courthouse, built in 1909, is a striking symbol of history and architecture in Monticello. This grand building stands in the heart of downtown and represents the city’s deep historical roots.

The courthouse, with its neoclassical design, has tall white columns and a stunning central dome, making it a great stop for history lovers and architecture enthusiasts. The courthouse’s interior features intricate woodwork and stained glass, adding to its charm. It’s not just a courthouse; it’s a reflection of the city’s past.

The building is more than a functional courthouse. It also serves as a cultural hub, often hosting community events and gatherings. The courthouse’s location at Courthouse Circle also makes it a natural starting point for exploring Monticello’s historic district.

Surrounding the courthouse are local shops, restaurants, and other historic buildings, so you can easily spend a day strolling around the area. Make sure to take some time to enjoy the picturesque view of this architectural gem.

Address: 1 Courthouse Circle, Monticello, FL 32344

2. Explore Letchworth-Love Mounds Archaeological State Park

Letchworth-Love Mounds Archaeological State Park is one of the most significant prehistoric sites in Florida. The park features one of the largest Native American mounds in the state, believed to have been built between 200 and 800 A.D. This site offers visitors a chance to step back in time and learn about the region’s early inhabitants.

As you explore the park, you’ll find well-maintained trails that lead you through lush woodlands. These trails offer beautiful views of the surrounding nature, and informative signs provide details about the mounds’ history. The centerpiece of the park is the large ceremonial mound, standing over 46 feet tall. You can also enjoy a picnic in the scenic surroundings, with facilities provided for visitors.

Letchworth-Love Mounds is a peaceful spot that combines the beauty of nature with the rich cultural history of Florida. Make sure to bring your camera to capture the scenic views and historic landmarks.

Address: 4500 Sunray Road South, Monticello, FL 32344

3. Tour the Monticello Opera House

The Monticello Opera House is a cultural treasure nestled in the heart of the city. This historic venue was built in 1890 and has served as a place for entertainment for over a century. With its Victorian architecture and vintage charm, the opera house is a must-see for visitors who appreciate art and history.

Inside, you’ll find a beautifully restored theater with ornate detailing and a cozy, intimate setting. The opera house regularly hosts performances ranging from plays to musical concerts, offering a variety of entertainment for all ages. It also serves as a community gathering space, hosting special events, weddings, and local festivals throughout the year.

Even if you can’t catch a show during your visit, the building itself is worth exploring. Tours of the opera house allow you to step back in time and experience the grandeur of the late 19th century. The Monticello Opera House is a key piece of Monticello’s history and culture, and a great way to spend an evening in town.

Address: 185 W Washington St, Monticello, FL 32344

4. Stroll through the Monticello Historic District

Monticello’s Historic District is a charming walk through time. As you stroll down its streets, you’ll notice the beautifully preserved homes and buildings, many dating back to the 19th century.

The district covers over 35 blocks and is a treasure trove of architectural styles, from Greek Revival to Victorian. Each building has its own story, and walking through the area gives you a sense of the rich history that shaped this quaint town.

Make sure to explore the residential areas where grand old homes are surrounded by ancient oaks draped in Spanish moss. You’ll also find historic landmarks like the Wirick-Simmons House and the Denham-Lacy House, which are testaments to the town’s deep-rooted Southern charm. Along your walk, stop by local boutiques, antique shops, and cafes that add to the district’s welcoming feel.

The Monticello Historic District is not only a delight for history buffs but also a peaceful place to unwind. Take your time to enjoy the scenery, snap a few photos, and soak in the relaxing atmosphere that makes Monticello feel like a step back in time.

Address: Downtown Monticello, FL 32344

5. Discover the Monticello Old Jail Museum

The Monticello Old Jail Museum offers a glimpse into the town’s past, specifically its law enforcement history. It was built in 1893, and served as the county’s prison for nearly 100 years. Today, it stands as a fascinating museum that showcases the life and times of prisoners, jailers, and the justice system of the late 19th and early 20th centuries.

As you step inside the brick building, you’ll be greeted by preserved jail cells, some of which still have the original iron bars. The museum features exhibits on the local sheriff’s department and the history of crime and punishment in Monticello.

The stories of past inmates and jailers provide a captivating, sometimes eerie, experience. Guided tours are available, where you can learn about the notorious figures who once occupied the cells and the conditions they endured.

The Monticello Old Jail Museum offers a unique way to explore the town’s history. It’s a small but mighty piece of the past, and definitely worth a visit if you’re in Monticello.

Address: 380 W Dogwood St, Monticello, FL 32344

6. Visit Christ Episcopal Church

Christ Episcopal Church in Monticello is not only a place of worship but also a historical landmark. The church was established in 1840. It has stood the test of time and remains a key part of the community. The beautiful Gothic Revival structure is surrounded by a peaceful, well-maintained garden that invites visitors to sit and reflect.

Inside the church, the atmosphere is serene, with tall stained glass windows and wooden pews that have hosted countless services over the years. The church also has a rich history, having been used as a hospital during the Civil War.

It’s easy to feel a connection to the past as you walk through the aisles, taking in the quiet beauty of the space. The Christ Episcopal Church is still an active congregation, but its doors are open to visitors who want to experience its historic and spiritual significance. 

Address: 425 N Cherry St, Monticello, FL 32344

7. Explore the Aucilla River

The Aucilla River is a hidden gem for nature lovers visiting Monticello. Flowing through North Florida, the river winds its way through scenic landscapes, providing a perfect backdrop for outdoor adventures. The Aucilla River is especially popular among kayakers and canoe enthusiasts due to its clear waters and lush surroundings.

The river is part of the Aucilla Wildlife Management Area, which is teeming with wildlife. You might spot deer, wild turkeys, and even alligators along the riverbanks. Birdwatchers will also enjoy the variety of species found here, including herons and egrets. If you’re a fan of fishing, the Aucilla River is known for its bass and catfish.

Whether you’re paddling downstream or just enjoying the peaceful atmosphere from the shore, the Aucilla River offers a tranquil escape into nature. There are several access points along the river, and it’s a great spot to spend the day exploring the natural beauty of Monticello’s surroundings.

Address: Aucilla River, Monticello, FL 32344

8. Attend a performance at Perkins Opera House

The Perkins Opera House is one of Monticello’s top cultural venues. This historic building, constructed in the late 19th century, still hosts a variety of performances throughout the year. From local theater productions to musical performances, there’s always something entertaining happening here.

Attending a show at the Perkins Opera House is a step back in time. The theater’s interior has been carefully preserved, with vintage seats, intricate woodwork, and a warm, intimate setting. The acoustics in the opera house are excellent, ensuring that no matter where you sit, you’ll have a great experience. The performances themselves range from classic plays to modern productions, so there’s something for everyone.

Perkins Opera House is a wonderful way to spend an evening in Monticello. The atmosphere, the history, and the entertainment make it a memorable experience.

Address: 185 W Washington St, Monticello, FL 32344

9. Hike in the surrounding natural areas

Monticello is surrounded by stunning natural areas, perfect for hiking enthusiasts. There are several trails that offer different levels of difficulty, so whether you’re an experienced hiker or just looking for a leisurely stroll, you’ll find a trail that suits you.

One of the top spots for hiking near Monticello is the Aucilla Sinks Trail. This unique trail takes you along the Aucilla River, where you can see fascinating geological formations called “sinks.” These are areas where the river disappears underground and re-emerges farther downstream. The trail is well-marked, and the landscape is filled with lush vegetation and wildlife, making it a beautiful place to explore.

Other nearby hiking spots include the Florida National Scenic Trail, which runs through parts of Jefferson County, and the Wacissa River Trail. Both offer scenic views, opportunities for wildlife sightings, and a peaceful atmosphere away from the hustle and bustle.

Hiking in Monticello’s natural areas is a great way to experience Florida’s unique ecosystems. Pack some water, wear comfortable shoes, and get ready to enjoy the outdoors.

Address: Aucilla Sinks Trail, 6517 N Salt Rd, Lamont, FL 32336

10. Visit the Lyndhurst Plantation

Lyndhurst Plantation is a stunning reminder of Monticello’s rich agricultural past. This historic plantation dates back to the 19th century and was once a thriving cotton plantation. The grand house and surrounding grounds give visitors a glimpse into the lifestyle of the era, showcasing the architecture and traditions of Southern plantations.

The plantation house itself is a beautiful example of antebellum architecture. Its large columns, spacious porches, and well-preserved interiors transport you back in time. Touring the house reveals antique furniture, period décor, and historical artifacts that paint a picture of life during the plantation’s prime.

The grounds of Lyndhurst Plantation are equally impressive. Lush gardens and ancient oak trees draped with Spanish moss create a peaceful and picturesque setting. The plantation also offers educational programs about its history and the role of plantations in Florida’s past, making it a thoughtful and engaging visit for history enthusiasts.

Address: 101 N Jefferson St, Monticello, FL 32344

11. Check out Bethel School

Bethel School is a historic one-room schoolhouse located just outside of Monticello. Built in the early 1900s, this simple wooden structure was once used to educate local children. Today, it serves as a fascinating museum that tells the story of rural education in early 20th-century Florida.

As you step inside Bethel School, you’ll see the original wooden desks, chalkboards, and teaching tools that were once used by both students and teachers. The small space is filled with artifacts, including old textbooks and photographs, that help visitors understand the challenges and triumphs of education during that time. It’s easy to imagine the lively classroom environment as you explore the preserved space.

Outside the school, you’ll find a quiet area surrounded by trees, providing a peaceful contrast to the bustling classroom that once existed inside. Visiting Bethel School is a great way to connect with Monticello’s local history and appreciate the role small schools played in shaping the community.

Address: Bethel Road, Monticello, FL 32344

12. Walk around Palmer House

Palmer House is another one of Monticello’s historic gems. This beautifully restored Victorian home dates back to the late 1800s and is one of the finest examples of Queen Anne-style architecture in the area. Walking around Palmer House gives you a chance to appreciate its intricate details, including the wraparound porch, turret, and decorative woodwork.

Inside the house, the grandeur continues with ornate fireplaces, stained glass windows, and period furnishings. The house is often open for tours, where knowledgeable guides share stories about the family who once lived there and the history of the home.

Each room offers a glimpse into a different aspect of life in the Victorian era, from the formal parlor to the cozy bedrooms. Surrounding Palmer House is a lush garden filled with blooming flowers and towering trees, making it a peaceful spot to take a leisurely walk. 

Address: 625 W Washington St, Monticello, FL 32344

13. Visit the Denham-Lacy House

The Denham-Lacy House is a stunning example of Monticello’s rich architectural heritage. The Victorian-style home, which was built in 1874, reflects the elegance and charm of the post-Civil War era. The house is known for its intricate woodwork, high ceilings, and beautifully preserved rooms that take you back in time.

Today, the Denham-Lacy House operates as a bed and breakfast, offering visitors a chance to experience its historic charm firsthand. The interior of the home is filled with antique furnishings and period décor, creating an atmosphere of warmth and nostalgia. Each room tells a story, from the ornate parlor to the cozy bedrooms, offering a glimpse into the lives of the families who once lived there.

The house is surrounded by well-kept gardens and towering trees, making it a peaceful retreat in the heart of Monticello. Even if you’re not staying the night, a visit to the Denham-Lacy House is a must for history buffs and those who appreciate historic architecture.

Address: 555 W Palmer Mill Rd, Monticello, FL 32344

14. Explore Palmer-Perkins House

The Palmer-Perkins House is another historic treasure in Monticello, known for its beautiful architecture and deep history. It was built in the mid-1800s and showcases Greek Revival design, a style that was popular in the South during that time. The house has been carefully preserved, allowing visitors to appreciate its grand columns, large windows, and expansive porches.

Inside, the Palmer-Perkins House boasts well-preserved original features like hardwood floors, tall ceilings, and intricate molding. It offers visitors a peek into the elegance of 19th-century living. The house is occasionally open for tours and special events, where guides share fascinating stories about the home’s past and its significance to the Monticello community.

The grounds of the Palmer-Perkins House are just as impressive as the interior. Lush gardens and mature trees surround the property, making it a serene place to explore. 

Address: 625 E Palmer Mill Rd, Monticello, FL 32344

15. Discover Wirick-Simmons House

The Wirick-Simmons House, built in the 1830s, is one of Monticello’s most iconic historic landmarks. This Greek Revival-style home is a testament to the town’s deep historical roots. The house has been meticulously preserved and is listed on the National Register of Historic Places. Its grand columns, wide porches, and classic Southern charm make it a favorite among visitors.

The interior of the Wirick-Simmons House is just as impressive as the exterior. You’ll find period furnishings, original woodwork, and décor that reflects the home’s early days. Each room has its own unique character, giving visitors a sense of what life was like for the wealthy families of Monticello in the 19th century. Guided tours are available, providing interesting insights into the history of the house and the people who lived there.

Outside, the grounds are beautifully landscaped with towering trees and a peaceful garden area. The house often hosts special events, such as historical reenactments and community gatherings, making it a lively part of Monticello’s cultural scene.

Address: 144 W Pearl St, Monticello, FL 32344

16. Take a Drive Through Scenic U.S. Route 19 and U.S. Route 90

One of the best ways to experience the charm of Monticello is by taking a drive along U.S. Route 19 and U.S. Route 90. These scenic highways offer a relaxing journey through rolling countryside, past historic landmarks, and under the shade of towering oak trees draped in Spanish moss.

U.S. Route 19 leads you through small towns and rural landscapes, providing picturesque views of farms and woodlands. Meanwhile, U.S. Route 90 offers a more historic route, passing through the center of Monticello with glimpses of old buildings, local shops, and cafes. Both routes are ideal for leisurely drives, allowing you to take in the peaceful atmosphere that defines this region of Florida.

Whether you’re a local or just passing through, this scenic drive offers a great way to appreciate Monticello’s beauty and charm. Roll down your windows, feel the fresh air, and enjoy the slower pace of life that these roads offer.

Address: U.S. Route 19 and U.S. Route 90, Monticello, FL 32344

17. Visit Monticello High School

Monticello High School holds a special place in the history of the town. The school, which was originally built in 1852, has served as an educational institution for generations. Though no longer in operation as a school, it stands as an important landmark in Monticello’s history. The building itself is a beautiful piece of architecture, with classic brick construction and large windows that reflect the educational values of the past.

Walking around the school grounds, you’ll feel the presence of the students and teachers who once filled its halls. The site is often included in local tours due to its historical significance. Monticello High School played a key role in the development of the community, and many residents still share fond memories of their time there.

Today, the old high school serves as a reminder of the town’s commitment to education and community spirit. Though it’s not open to the public regularly, the building’s exterior is worth a visit, especially for those interested in local history and architecture.

Address: 425 N Mulberry St, Monticello, FL 32344

18. Experience Local Dining in Downtown Monticello

Downtown Monticello is the place to be if you want to experience the town’s local dining scene. Small, family-owned restaurants and cafes line the streets, each offering a taste of Southern hospitality and comfort food. Whether you’re craving a hearty breakfast, a casual lunch, or a delicious dinner, you’ll find plenty of options to choose from.

One of the highlights is Tupelo’s Bakery & Café, known for its fresh, homemade breads, sandwiches, and pastries. If you’re in the mood for something more Southern, head to Rev Café, where fried chicken and shrimp po’boys are local favorites. For an elegant dinner, stop by Brick House Eatery, where the menu features a mix of classic dishes and contemporary twists, all made with local ingredients.

What makes dining in Monticello special is the friendly, relaxed atmosphere. The restaurants here aren’t just about food—they’re about community. Many places feature outdoor seating, allowing you to enjoy the town’s pleasant weather while you eat. Be sure to save room for dessert, as many spots offer homemade pies and cakes that are simply too good to pass up.

Address: Downtown Monticello, FL 32344

19. Explore Howard Academy

Howard Academy is a historic site in Monticello with deep cultural significance. Established in 1936, it was originally built as a school for African American students during segregation. The academy stands as a reminder of the town’s educational history and the resilience of its African American community.

Today, Howard Academy is preserved as a historic site. The building itself has retained much of its original character, with simple, sturdy architecture that reflects the era in which it was built. Inside, visitors can explore exhibits that showcase the history of the school, its students, and the community’s journey toward integration. Photographs, personal stories, and artifacts give a detailed account of the school’s impact on the local population.

The grounds around Howard Academy are peaceful, providing a quiet space to reflect on the progress and challenges of the past. A visit here offers not only a chance to learn about Monticello’s educational history but also an opportunity to appreciate the importance of preserving such significant landmarks.

Address: Mamie Scott Drive, Monticello, FL 32344

20. Visit the Monticello Historic Cemetery

The Monticello Historic Cemetery, established in the early 1800s, is one of the oldest cemeteries in the area, with gravestones that date back centuries. Many prominent local figures, including war veterans and early settlers, are buried here. Walking through the cemetery offers a glimpse into Monticello’s past and the lives of those who shaped the town.

The cemetery is well-maintained, with towering oaks and moss-draped trees adding to the peaceful atmosphere. Each gravestone tells its own story, and some feature intricate carvings and designs that reflect the customs of different time periods. There are also guided tours available, offering insights into the history and significance of the cemetery and its inhabitants.

Visiting the Monticello Historic Cemetery is a reflective experience. It connects you to the town’s rich history in a quiet, contemplative setting. It’s an ideal stop for those interested in genealogy, history, or simply seeking a moment of calm amid Monticello’s bustling streets.

Address: 425 N Jefferson St, Monticello, FL 32344

21. Tour Local Antique Shops and Galleries

Monticello is a haven for antique lovers and art enthusiasts. The town’s charming downtown area is home to several antique shops and galleries, each offering a unique collection of treasures. Whether you’re searching for vintage furniture, rare collectibles, or handmade art, Monticello’s local shops provide a delightful experience.

One of the popular stops is The Vintage Chandelier, where you’ll find an eclectic mix of antiques, from rustic farmhouse décor to elegant chandeliers.

For those who love discovering hidden gems, Monticello Antiques Marketplace is a must-visit, with its vast selection of items that range from old books to classic toys. Art lovers will enjoy stopping by the Jefferson Arts Gallery, where local artists showcase their paintings, pottery, and sculptures.

Browsing these shops and galleries is a leisurely activity that lets you uncover unique finds while supporting local businesses. The owners are friendly and often eager to share stories about their collections. Even if you don’t buy anything, it’s a fun way to explore Monticello’s creative side and appreciate the craftsmanship of past eras.

Address: Downtown Monticello, FL 32344

22. Participate in Local Festivals or Events

Monticello is a small town with a big sense of community, and one of the best ways to experience this is by attending one of its many local festivals or events. Throughout the year, Monticello hosts several gatherings that bring residents and visitors together to celebrate everything from local history to seasonal produce.

One of the most popular events is the annual Watermelon Festival, which has been held for over 70 years. This lively festival features a parade, live music, arts and crafts, and, of course, plenty of fresh watermelon. It’s a fun, family-friendly event that showcases Monticello’s agricultural heritage.

Another notable event is the Southern Music Rising festival, which celebrates local and regional musicians. Music lovers can enjoy a variety of performances, from country to blues, all in a relaxed, outdoor setting.

There are also arts and crafts booths, food vendors, and plenty of activities for the kids. These local festivals and events are a wonderful way to experience the culture and warmth of Monticello. 

Address: Various locations around Monticello, FL 32344

23. Explore the Natural Beauty of Lake Miccosukee

Lake Miccosukee is one of Monticello’s natural treasures and a must-visit spot for outdoor enthusiasts. This large, shallow lake is located just a few miles outside of town and offers a peaceful escape into nature. Surrounded by wetlands and cypress trees, the lake provides a stunning backdrop for a variety of outdoor activities.

Fishing is a popular pastime at Lake Miccosukee. The lake is home to bass, catfish, and bream, making it a favorite spot for both amateur and experienced anglers. The quiet waters and abundant fish make it an ideal place to spend a relaxing day casting a line. Boating is also common here, with several boat ramps available for easy access to the lake.

For those who prefer staying on land, the area around Lake Miccosukee is great for birdwatching. The wetlands attract a wide variety of bird species, including herons, egrets, and even bald eagles. It’s a serene spot for a nature walk or a quiet picnic.

Exploring Lake Miccosukee is the perfect way to experience the natural beauty of Monticello and unwind in a tranquil setting.

Address: Lake Miccosukee, Monticello, FL 32344

Final Thoughts

Monticello, FL, offers a perfect blend of rich history, natural beauty, and vibrant local culture. Its warm, welcoming atmosphere and variety of attractions make it a great destination for all ages.

From scenic drives to engaging festivals, Monticello gives visitors an authentic taste of Southern charm. This hidden gem provides a memorable experience for anyone looking to explore Florida’s quieter side.