The Rolling Hills of Brooksville, Florida

The Rolling Hills of Brooksville, Florida

Heading north on SR 41 fifty miles north of Tampa, rolling hills appear on the horizon. Chinsegut Hill is one of Florida’s highest points at 269 feet.  Only a couple of locations along the Lake Wales Ridge which spans the spine of the state boast a greater height. There are so many picturesque places in Florida to explore, yet so few that match the charm of a 5 square mile town nestled in the rolling hills of eastern Hernando County. This is Brooksville, a place where you may forget you are still in Florida.  The rolling hills of Brooksville are a special destination on an otherwise sprawling coast.

The Main Street Eatery has the best peanut butter pie!
Main Street Eatery in Downtown Brooksville

As a child, I remember those Sunday afternoon drives through wherever my father felt like going that day. Everyone piled in the car, and off we went sometimes to nowhere in particular. My brother and I usually ended up asleep in the back seat. I can’t think of a better Sunday drive than veering onto one of the narrow back roads and driving through the eastern Hernando rolling hills.

History of Brooksville

Forest-covered limestone and ancient sand dunes define this part of the state. The historic city of Brooksville lies twelve miles southeast of Florida’s geographic center. Even its location has a unique story. Hernando County was once triple the size of what it is today. In 1877, the state separated it into three counties, Pasco to the south and Citrus to the north. Back in 1856, four families established the city of Brooksville; the Howells to the north, the Mays to the east, the Hales in the west, and the Parsons to the south. Named after, Preston Brooks, a South Carolina congressman, their new town of Brooksville was a consolidation of two communities established in the 1840s called Melendez and Pierceville.

The land surrounding Melendez and Pierceville was essential to trade along the west coast of Florida. Ft. Desoto (no relation to the Ft. Desoto in Pinellas County) served as not only a stop for the Concord Stage Line that ran from Palatka to Tampa, but also as a trading post and as protection for settlers from Seminole Indians. The abandonment of the fort is what actually gave rise to city of Brooksville. While the high terrain made the Fort location attractive, they constructed it on a bed of limestone which made obtaining water difficult. The settlers eventually abandoned the location and moved just to the southwest. Their new settlement became Brooksville. A private residence now sits on the landmark location where the old fort once stood.

While the nation fought the Civil War in the 1860s, eastern Hernando County supplied Confederate soldiers with cotton and lumber. In 1864, Union troops attacked the Confederate-held city of Brooksville to destroy the supply line. Despite a valiant attempt to protect the city, the Union army defeated the Confederate troops in what is now known as the Brooksville Raid. The Hernando Historical Museum Association and the North Pinellas County Scout Sertoma Club reenacts the event each January near Weeki Wachee.

Things to do in Brooksville

Today, Brooksville is famous for more than just the surrounding rolling hills. Historic southern homes line cobblestone streets reminiscent of those you find in Savannah, Georgia or Charleston, South Carolina. Take a walking tour through the downtown where buildings and businesses date back to the early 1900s. Grab lunch or afternoon tea at The Tilted Teacup. Then, visit the May-Stinger House Museum. Check out a Train Depot Museum from the late 1800s or a one room schoolhouse still standing, all within walking distance from one another. It’s easy to spend an entire day exploring this quaint historic town.

Things to do around Brooksville

The area around Brooksville, known locally as The Nature Coast, is an outdoor lover’s dream! Once home to settlers and Seminoles, the Chassahowitzka Wildlife Management Areas sit to the east and west. The Withlacoochee State Forest provides the anchor. One of the most attractive areas to outdoor enthusiasts is the Croom Wildlife Tract near Ridge Manor, a 20,000-acre wildlife area featuring dozens of miles of hiking, horseback riding, bicycling and motorcycle trails. The hilly terrain makes it great for getting into shape to do longer more strenuous hikes in the mountains or anywhere else you may find yourself exploring in the future. Silver Lake is ideal for hunting or camping. Fish or kayak the 13 miles of the Withlacoochee River that cuts through the Croom Tract. The Florida National Cemetery rests along the east border. Interstate 75 provides easy access to everything.

The Croom Tract is a great place to hike

When someone says Florida, the obvious images that come to mind are usually those of beaches and palm trees. However, there are some parts of Florida that get so little attention, they are practically unknown.  These treasures don’t fit the ideal portrait of sun and sand. You won’t find them on a brochure inside your local travel agent’s office. Some who have lived here all their lives know as much about them as someone who lives hundreds of miles away. Brooksville may be a sleepy town. Some may consider it dull or the lifestyle slow. The beauty of a gem is that on the surface it looks like a rock. It’s not until you crack it open to look deeper that Brooksville revelas the beauty within its crusty shell. Brooksville is the gem of the Nature Coast.

Historic Brooksville Neighborhood

Visit Brooksville

So, The next time you are sitting in the living room with that urge to get out and do something new, think of how it was a century ago. Automobiles gave rise to the afternoon drive allowing entire families to get out and explore their surroundings. They loaded the car and drove into the untamed countryside for a picnic or maybe to a neighboring town to see old friends or family. The automobile brought people together and they put towns on the map. The automobile made it possible for sleepy old towns like Brooksville to shed its outer crust and expose the extraordinary beauty within. The world may have changed. Technology may have evolved. But people will always have that desire to explore, to get out on the open road and find something hidden, something extraordinary! And there is nothing more extraordinary than those rolling hills of Brooksville?

Get Directions

Brooksville is located on US Hwy 41 in Hernando County about 50 miles north of Tampa.