By  Mike Miller  Updated June 2, 2023

Monticello, Florida Things To Do, Lodging, Dining, & Real Estate At End Of Article

Monticello is the county seat of Jefferson County.  The county was named after Thomas Jefferson.

The town named after his home is located about 20 miles east of Tallahassee.

Jefferson County CourthouseJefferson County Courthouse

The name of the town is not pronounced like Jefferson's famous home in Virginia, however.

It is....... MONTI-I-SELL-O,
not........ MONT-I-CHELL-O.

The population is about 2,569 people. It is a small working class southern town that serves not only as the county seat, but as a supply center for the surrounding farms.

Jefferson County is very old by Florida standards, being chartered in 1827 when Florida was still a territory.

Bailey-Brinson HouseBailey-Brinson House

Monticello is a pretty little town with giant oak trees forming canopy streets and a lot of old restored homes, many of them going back to before the Civil War.

Many of these homes were restored during the Great Depression of the 1930's.

Main Street in Monticello is a Florida Main Street Community, and has historic sites such as the 1890 Perkins Opera House and the recently restored 1906 County Courthouse.

The opera house is still functional and puts on musical and theater performances, and the ground floor ballroom is a local gathering and meeting place.

Monticello Florida Christ Episcopal ChurchChrist Episcopal Church

There is also one of the prettiest Carpenter Gothic churches in all of Florida in the Monticello Historic District.

Christ Episcopal Church is at 425 North Cherry Street.

The Dun Rovin Motel in Monticello Has Dun Gone Into HistoryThe Dun Rovin Motel in Monticello Has Dun Gone Into History


Jack YoungbloodJack Youngblood

If you are a Florida Gator football fan, you may know Monticello is famous as the boyhood home of Pro Football Hall of Famer Jack Youngblood.

Jack went to Monticello-Jefferson County High School and graduated in 1967.

He helped his team go to the state playoffs, and was voted as one of the State of Florida's 33 greatest high school football players of all time.

He had a great college career at the University of Florida, and an equally great career with the Los Angeles Rams of the NFL.

He is enshrined in the Pro Football Hall of Fame in Canton, Ohio.

Jefferson County likes to refer to itself as the "Keystone County" because it is the only Florida county that reaches from the Georgia state line all the way south to the Gulf of Mexico.

The old saying in Florida is that south Florida is northern, and north Florida is southern.

That is certainly true of Monticello, a true gem of an old southern City.

John Denham House, Built in 1872, Now a B&BJohn Denham House, Built in 1872, Now a B&B
Photo Courtesy Phil Eschbach


The Cottage Bed & Breakfast, 295 W. Palmer Mill Road, Monticello, FL 32344. Tel: 850-342-3541. Set among peaceful green fields and old oaks. Each room has a queen bed, european decor, sitting area, private bath, cable tv, comfy robes and central heat/air. 

1872 John Denham House, 555 W. Palmer Mill Road, Monticello, FL 32344. Tel: 850-997-4568.  This is a beautiful restoration of the house that was built in 1872.  It has eight fireplaces and a lot of beautiful antiques on an acre of land. 



190 N. Jefferson Street
Monticello, Florida 32344
Tel:  850-997-2100

When we are traveling around Florida we like to find nice local restaurants to eat in.  We like to go where the locals go.

Brick House Eatery is one such restaurant.

Brick House Eatery, MonticelloBrick House Eatery, Monticello

It is open for breakfast, lunch, and dinner.  You can expect to see close to a full house when you visit.  It is very popular, but service is fast and a wait is reasonable.


An interesting side trip when visiting the town is Monticello Vineyards and Winery.  You can have a nice tour and enjoy sipping some good wine.


Monticello Opera House 
185 W. Washington St, Monticello, FL 32344 | (850) 997-4242 
As discussed earlier on this page, the Opera House dates back to 1890 and continues to host a wide array of performances, from plays and concerts to community events.

This historic venue not only offers entertainment but also a glimpse into the architectural elegance of a bygone era. It’s our favorite spot for those who appreciate the arts and the stories embedded in historic structures. 

Jefferson County Historical Association Museum 
230 N Jefferson St, Monticello, FL 32344 | (850) 997-2465 
Located in the heart of Monticello, this museum is housed in a beautiful 19th-century home and offers insights into the local history and heritage. Artifacts, photographs, and documents are on display. 

Visitors can explore the rich tapestry of life in Jefferson County over the years. It’s a must-visit for history buffs eager to learn about the area's past and its impact on the present. 

Letchworth-Love Mounds Archaeological State Park 
4500 Sunray Rd South, Monticello, FL 32344 | (850) 922-6007 
Just a short drive from Monticello proper, this state park is home to Florida’s tallest Native American ceremonial mound. The site offers a fascinating look into the lives of the ancient people who once inhabited the area.

Nature trails and interpretive signage make it a great place for a peaceful hike with an educational twist. It’s our favorite spot for those interested in archaeology and the natural beauty of Florida. 

Monticello Vineyards & Winery 
1211 Waukeenah Hwy, Monticello, FL 32344 | (850) 294-9463 
I have a link earlier on this page to a more in-depth article I wrote about the winery. A self-described “small and unpretentious Florida farm winery”, this family-owned winery is set amidst the rolling hills of Jefferson County.

With tastings and tours available, visitors can learn about the wine-making process and sample a variety of wines produced from locally grown grapes. It’s a perfect activity for those looking to enjoy the scenic countryside while indulging in local flavors. 

Avera-Clarke House Bed & Breakfast 
580 W. Washington St, Monticello, FL 32344 | (850) 997-5007 
For a truly charming stay, consider booking a room at this historic bed and breakfast. The beautifully restored home offers cozy accommodations and a glimpse into the gracious living of the early 1900s.

With its warm hospitality and delightful breakfasts, it’s a great place for those seeking a memorable and relaxing experience. 

Econfina River State Park 
4384 Econfina River Rd, Lamont, FL 32336 | (850) 922-6007 
Less than 20 miles away, nature lovers will delight in the pristine beauty of Econfina River State Park, where the unspoiled Econfina River meets the Gulf of Mexico.

Offering kayaking, fishing, hiking, and bird watching, the park is a haven for outdoor enthusiasts. Its remote location provides a peaceful setting for enjoying Florida’s natural landscapes. 

Interactive Google Map of Monticello, Florida

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