By  Mike Miller  Updated February 13, 2023

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

Brooksville, Florida is 50 miles north of Tampa and just a few miles east of Weeki Wachee Springs on State Road 50.  Its population is 8,191. 

Like many Florida cities, Brooksville has been dwarfed by a huge next door development that created many thousands of new homes.

Watercolor of Old Truck at Florida Cracker KitchenWatercolor of Old Truck at Florida Cracker Kitchen

Its neighbor to the west, Spring Hill, now has a population of 111,076.  Brooksville is more than 100 years older than Spring Hill and less than 1/10th the size.


There were early Native Americans in the area when Hernando deSoto came by in the 1500s.

Chocochattee Town, near Brooksville, was the de facto seat of government for the Seminole nation for almost 70 years going back to 1767.

Fort DeSoto was built on the north side of what is now Brooksville during the Seminole Wars in the 1840s. 

Brooksville Decorative Water Tower
Brooksville Decorative Water Tower
Photographic Destinations by Bob Kyle

There was no well water available at the fort because of the underlying limestone formation, so the fort moved to an area with freshwater springs that were on the site of the future Brooksville.

The fort became a regular stop on the stage coach line that ran from Palatka to Tampa.

Settlers began arriving in the late 1840s and created two new communities,  Pierceville and Melendez. 

These communities merged in 1856 and became known as Brooksville, named for Congressman Preston Brooks of South Carolina.

Read More About the History of Brooksville, Florida


The history of Preston Brooks that inspired the town's name does not fit with its peaceful demeanor of today.

Lovely ancient oaks line the brick streets. Grand well maintained southern mansions stand proudly in quiet neighborhoods.

Mansion in Brooksville, FloridaMansion in Brooksville, Florida on Brooksville Avenue

It is within a long commuter's drive of Tampa and an ever increasing number of Tampa workers are making the trip, especially since the completion of the Suncoast Parkway, a toll road.

Hernando County CourthouseHernando County Courthouse in Brooksville, Florida

Although a medium sized town, it is easy to get lost in Brooksville because of the many state and federal highways that meander through town in a most unusual way.

The highway network in Brooksville, FloridaThe Highways That Go Through Brooksville, Florida

For example, US-41 comes into town from the southwest, then turns east through town before going north again.

US-98 comes in from the southeast, then turns west before going north again.

State Road 50 bypasses the town on its south side, but State Road 50A goes directly through town.

All of these highway confluences result in a series of one way streets that locals have no problems with but that confuse tourists.

Confederate Monument in Brooksville, FloridaConfederate Monument in Brooksville, Florida

The weather worn statue of a confederate soldier still stands guard in front of the Hernando County courthouse in downtown Brooksville.

Brooksville AvenueBrooksville Avenue, Brooksville, Florida

The downtown area has not been gentrified like in so many Florida towns.

It is a collection of interesting old buildings and quite a few that have seen better days.

Brooksville Avenue homeHome on Brooksville Avenue

It's a real town where people live, work, play and enjoy the many good restaurants in the area.

Unlike most of table-flat Florida, Brooksville and Hernando County have many rolling hills. Some of them are among the highest elevations in Florida.

Chinsegut Hill Manor HouseChinsegut Hill Manor House

One of the most interesting attractions in Brooksville is Chinsegut Hill Manor House, known locally also as Mount Airy, Snow Hill or just The Hill.

This is a historic site that was originally the plantation of Colonel Byrd Pearson from South Carolina who named his sprawling estate "Mount Airy".  

The house was partially completed before Florida became a state. The property has had other uses and names over the years.


Another place that's fun to visit in Brooksville is the Hernando Heritage Museum at 601 Museum Court.  It is located within the historic May-Stringer House. 

May-Stringer HouseMay-Stringer House

The house is on the National Register of Historic Places, and features many artifacts and Victorian era rooms.


Recommended Brooksville Restaurant


101 North Main Street
Brooksville, Florida
Tel 352-799-2789

The Main Street Eatery has been serving homemade lunch, and only lunch, since it was opened in 1989 by Mr. and Mrs. Bill Bell. 

Main Street EateryMain Street Eatery

It is very popular with the locals who work in the nearby shops and government buildings, but it has also been discovered by tourists.

The paper table mats have ads for many of the downtown Brooksville businesses, so it is a good place to get oriented.

The Eatery has a delicious selection of sandwiches, salads, soups and desserts. Their offerings range from healthy to decadent.

For example, you can have their house salad with garden fresh veggies, celery and carrots and a healthy dressing.

Or you can also have their Buzzard Breath Chili, a spicy concoction topped with Cheddar Cheese and crispy tortilla chips.

If you can eat one bowl of this hot chili, the second bowl is free.

They serve spicy chicken wings, cheese nachos, pasta salad, Greek salad, and even have a diet platter made with Jell-O and cottage cheese.

All of their sandwiches are made using 97% fat free meats.

They proclaim that their Cuban sandwich is the finest north of Havana. That would include those in Miami, of course, so that is quite a claim!

Main Street EateryMain Street Eatery

My favorite soup at this cozy small restaurant is their "Bill's Famous Cajun Bean with Hamburger Soup". 

This delicious meal is not as spicy as the chili, and is sometimes made with three or four different kinds of beans.

I once asked Mrs. Bell for the recipe and was politely refused, so I just have to keep going up there to have it when the craving hits me.

The interior of Main Street Eatery is "retro art deco", with a small counter and maybe two or three booths and ten tables.

It's smack dab in the middle of historic downtown Brooksville.

They even have free WiFi if you get lonely for your e-mail.

More Photos Kyle


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