Quick Brooksville, Florida History

Brooksville, Florida was originally known as Melendez and then Benton. Incorporated in 1856, it is a wonderful city featuring a hilly terrain that ranges in elevation from 175 to 274 feet. There is a long history of successful planters, growers, and cattlemen in and around Brooksville.

Its southern background is reflected in its name, honoring South Carolina Congressman Preston Brooks who is best noted for hitting abolitionist Senator Charles Sumner on the head with his cane.

Brooksville’s downtown area features the iconic Hernando Courthouse, along with great shopping in unique stores featuring everything from antiques, outfits, high-end resale, stationery, flowers and bric-a-brac to formal gowns – and stationery. Some streets still show the Augusta bricks laid by hand.

Things to Do in Brooksville, Florida

There are several downtown restaurants and coffee shops, along with legal and banking offices, a library, and more than one park. Brooksville has been working hard to revive its downtown to attract more visitors and became a Florida Main Street community in 2016.

For those looking for things to do in Brooksville, the Main Street organization holds several events in Brooksville’s downtown area as well as farmers and artist markets, and a simply magical holiday celebration of all things Christmas during December with everything from musical trees to performing artists, decorations galore and horse-drawn carriage rides. 

Local art is displayed in several downtown businesses and buildings, as well as murals painted throughout the downtown area. A walking tour map of the downtown murals may be found here.

The Brooksville City Hall building houses a changing art exhibit in Gallery 201, and all are welcome. There is no charge.

The architecture is interesting in several buildings and when looking for things to do in Brooksville, Florida, a wonderful historic walking tour can be had for the simple act of following the map here. If you would like more information about each building on the historic tour, download the complete guide here. (Please note that the Hernando Chamber of Commerce has moved to Brooksville’s Tampa Bay Regional Airport. The guide is dated, but the history and map are accurate.)

Another popular thing to do in Brooksville, Florida, is to visit the May Stringer Museum, located at 600 West Jefferson. Housed in the 1850 Stringer House, a Queen Anne masterpiece with a four-story tower, this historic building is reputed to be haunted. There are daily tours Tuesday – Saturday led by docents and the price of admission is only $10 for adults, $5 for children, free for those under 6 years of age, but the exhibits seem more adult-friendly.

F. L. Stringer was a State Senator and judge. With thousands of historic artifacts and regular tours, it commemorates the Civil War era and provides a glimpse at the lifestyle and relics of a gone but not forgotten segment of American history. Ghost tours are held on Friday and Saturday nights by reservation.

In addition to the May Stringer house there is a historic train depot to visit. Next to the historic train depot museum is a one-room schoolhouse to visit on Russell Street. Both of these museums are adjacent to Russell Street Park which has the Good Neighbor Trail running through it.

The Good Neighbor Trail is a paved, multiuse trail that runs about 10.3 miles to connect with the Withlacoochee State Trail.

Continue east to find another wonderful shopping area, featuring the Hawkins House and the Florida Cracker Trading Company and Tap Room. There is even an old-fashioned Coney Island where it is rumored that Elvis Presley may have eaten many years ago with an ice cream shop in front.

The Florida Mermaid Trail

In 2020, a Mermaid Trail was created in downtown Brooksville, which is part treasure hunt and part walking tour. It is an easy activity for one or more to get out and enjoy the historic brick streets and well-kept homes and businesses. Each February, a Mermaid Festival is held in Hernando Park, where residents and visitors compete for the best-dressed mermaids, with and without their pets, and meet the real mermaids of Weeki Wachee Springs State Park. The maps for the Mermaid Trail can be found at Florida’s Adventure Coast Visitor Center, adjacent to the park.

Expanding Beyond Brooksville’s City Limits

You may want to travel north on US 41 to visit the historic Chinsegut Hill Historic Site and rediscover the magic that caused its last private owners to name it Chinsegut, meaning, “a place where lost things are found.” Learn their story of courage and civil rights for all, as well as a historic timeline of occupation during significant national events. And it’s beautiful and somewhat magical.

*Please note that Chinsegut Hill Museum is managed by the Tampa Bay History Center and is open on weekends for tours, as well as some outdoor events on select weekdays. An Emancipation Celebration is held in May.

Don’t forget the Ice Cream

Head back south on U.S. 41 and then travel east on S.R. 50/U.S. 98. Make a right on Spring Lake Highway (541) and follow it to the top of the hill. On the right is Boyett’s Grove Citrus and Timeless Attraction. Here you will find a wonderful animal park where you can feed the animals, a dinosaur cave, taxidermy museum, birds, snakes, an alligator named, “Elvis”, and more.

A putt-putt golf course winds through part of this fun-filled tourist trap. There’s even a snack bar, ice cream parlor, and an old-fashioned Florida gift shop! It’s one of my favorite places on the Nature Coast.