Brooksville punches well above its size. And I really mean that.
Most people have never even heard of it, and there are others who’ve usually only known it as “the town near Weeki Wachee.” But this small town in Florida (about an hour north of Tampa) has great history, natural wonders, good wine, and one of the most legitimately mysterious historic houses in the state, all within a few miles of each other.
The more you come back and the longer you stay, the more exciting things you’ll discover in and around town.
This guide covers what to do in Brooksville, where to eat, and who this town is really for. If you’ve been wanting to experience an Old Florida road trip or just looking for a day trip from Tampa that doesn’t involve long theme park lines, then Brooksville belongs on your list.
For more small towns like this one, check out my full guide to 12 Charming Small Towns in Florida Worth the Detour.
🏨 Where to stay:
Dolan House Bed and Breakfast – A beautifully restored historic home right in downtown Brooksville. Small, charming, and within walking distance of the May-Stringer House and the mural trail. The most character-rich option in town.
Hampton Inn Brooksville – Clean, reliable, and the best standard hotel option near town. Good breakfast included and easy highway access if you’re road tripping from Tampa.
🍴 Where to eat:
Florida Cracker Kitchen – Hand-cracked eggs, scratch-made tomato gravy, and oversized cinnamon rolls. The most Brooksville breakfast you can get – order the Cowboy Corned Beef Hash.
Green Door on Broad – Elevated Southern cuisine in a charming downtown setting. Consistently praised for the ribeye and the glazed honey maple salmon. Reservations recommended on weekends.
Good Time – Natural wines, Florida craft beers, and rotating food trucks in a laid-back downtown spot. Perfect afternoon stop between the winery and the mural trail.
🎟️ Best things to do:
May-Stringer House Late-Night Tours – 6-hr Paranormal investigation inside one of Florida’s most documented haunted buildings. Runs Saturdays 8 pm-2 am and sells out months in advance. Book early.
Weeki Wachee Springs Clear Kayak Tour – Paddle the spring run fed by 117 million gallons of water daily. The clarity is extraordinary – you can see straight to the bottom the entire way.
Sparacia Witherell Winery – A 30-acre family-run muscadine vineyard with free tastings, a shaded patio, and no rush whatsoever. One of the best small wineries in Florida.
Chinsegut Hill Historic Site – Free to visit. One of Florida’s highest natural elevations at 240 feet, with trails through the preserved grounds of a former cotton plantation that once hosted Thomas Edison and Helen Keller.
Travel Tip: Brooksville is about an hour north of Tampa – easy as a day trip, but the May-Stringer House paranormal investigations run until 2am, so if that’s on your list, book a hotel and make it an overnight. The Dolan House puts you steps from the action.
What Not to Miss in Brooksville
1. May-Stringer House
The May-Stringer House is a four-story, 14-room Victorian “Painted Lady” that has been standing since 1855. It’s on the National Register of Historic Places and is considered one of the most haunted buildings in Florida.
There is so much history here. The original owner, John L. May, purchased the land in 1855 and built a modest four-room home for his wife, Marena and their two daughters. He died of tuberculosis just three years later.
Marena stayed through the Civil War, eventually remarried Confederate soldier Frank Saxon, and then died in 1869, giving birth to their daughter Jessie Mae. The baby survived, but only for three years before she too passed away from unknown causes.
John, Marena, Jessie Mae, and an infant son who died weeks after birth are all buried in the backyard of the property.
After the Mays and Saxons, the house passed to Dr. Sheldon Stringer, who expanded it from four rooms to fourteen and used it as both a family home and medical practice, which eventually led to more deaths in the property.
Today, the Hernando Historical Museum Association operates the property as a museum with over 10,000 artifacts on display. The rooms are set up by theme: a Victorian dining room, period bedrooms, a military room, an 1880s doctor’s office and a 1900s communications room.
Throughout the years, the May-Stringer house has been known as a very active paranormal hot spot. Paranormal investigators have documented cold spots, shadow figures, orbs of light, and the sound of children crying.
The most active ghost is said to be Jessie Mae herself, the three-year-old who died in this house and whose room still carries something heavy in the air.
When I walked into Jessie Mae’s room, it felt like stepping into a void. It was the kind of quiet that didn’t match the rest of the house and “empty” in a way that felt intentional. This room has quite the energy, but nothing compared to the attic.
The attic is a different energy entirely. That’s where “Mr. Nasty” lives, also called Gary. The spirit is believed to have arrived inside an antique wooden chest, the kind used for magic tricks or theater performances back in the day.
As I stood in front of that chest, the air felt thick and off. Not evil exactly, but heavy and dark. For that reason, I didn’t linger.
Out front, two time capsules are buried in the yard. One is from Merrit Funeral Home, to be opened February 19, 2100. The other is from Brewer Memorial Funeral Homes, scheduled for February 26, 2044. A strange detail that adds to the layered weirdness of this place.
The museum offers daytime history tours that begin on the hour, with the last tour starting at 2 pm. But if you’re serious about the paranormal side, the late-night investigations and ghost tours are a must.
These happen on select Fridays and Saturdays throughout the year, but they often sell out well in advance, often months ahead, so book early through the Hernando Historical Museum Association.
Address: 601 Museum Court, Brooksville, FL
2. Chinsegut Hill Historic Site
Chinsegut Hill (chin-SEE-gut) sits at one of the highest natural elevations in Florida, roughly 260 feet above sea level. That might not sound like much, but in a state known for being almost entirely flat, it’s quite noticeable and the landscape here feels completely different.
The word chinsegut comes from the Inuit Indians and means the “spirit of things lost and regained”.
The property dates back to the 1840s, when it was a cotton plantation, with the Manor House built in 1842 and passed through several significant owners over the decades.
In the 1920s and 1930s, the estate was owned by Colonel Raymond Robins and his wife, Margaret Dreier Robins, prominent social reformers who hosted progressive-era luminaries such as Helen Keller, Thomas Edison, and author Marjorie Kinnan Rawlings.
The Robins family eventually donated over 2,000 acres of land to the federal government for agricultural research. Later, an additional 114 acres were incorporated into the Chinsegut Wildlife and Environmental Area.
The Manor House on the property is preserved as a historic site and is listed on the National Register of Historic Places.
It’s free to visit. The grounds are open for exploring, and the house can be toured on certain days. Worth the stop if you’re spending a full day in Brooksville.
Address: 22495 Chinsegut Hill Rd, Brooksville, FL
3. Weeki Wachee Springs State Park
It’s almost certain that one of your family members or a friend visited this park as a kid.
The famous live mermaid shows have been running here since 1947, making Weeki Wachee one of Florida’s oldest and strangest roadside attractions.
Performers in mermaid tails swim underwater in a natural spring, performing choreographed routines while breathing through air hoses. It’s pure Old Florida fun, if you ask me.
Beyond the mermaid theater, Weeki Wachee Springs State Park sits at the headsprings of the Weeki Wachee River, one of the clearest and most beautiful paddling runs in the state.
The spring pumps out roughly 117 million gallons of fresh water daily, and the visibility is surreal. You can rent kayaks or paddleboards at the park and float the spring run, watching fish and turtles below you in water so clear it almost doesn’t look real.
There’s also a swimming area at Buccaneer Bay, which is essentially a water park fed by the spring. In summer, this is where locals come to cool off.
Weeki Wachee is about 20 minutes from downtown Brooksville and it’s a must-visit for kayaking. Oh, and the mermaids, of course.
Address: 6131 Commercial Way, Spring Hill, FL
Dames Cave at Withlacoochee State Forest
Dames Cave is one of those little surprises that doesn’t fit the mental image most people have of the state. It’s the same way I feel about the caverns in Marianna. Who knew Florida had such a vast cave system!
At just about a 15-minute drive from Downtown Brooksville, this moderate hiking trail through Withlacoochee State Forest leads to a cave system in the Citrus Tract with 37 dry caves discovered to date. And while most of them are closed to the public, Dames Cave is not.
The cave’s main chamber ceiling has collapsed, exposing a big opening from which you can look down into the cave. On one of the sides, there is a gap through which you can enter to explore the cave. This cave is also known as Vandal Cave due to the graffiti on its limestone walls.
It’s not a massive cave system, but it’s atmospheric and worth the hike, especially if you’re someone who likes finding the weird corners of a place.
The Withlacoochee State Forest also has the Croom Tract, which offers some of the best off-roading for dirt bikes and ATVs. Miles of trails wind through the woods, ranging from beginner-friendly to genuinely challenging. If you’re traveling with bikes, this is a destination in itself.
There is a parking area for Dames Cave right off of S Lecanto Hwy, on the right side going northbound. No admission fees.
Address: 10701 S Lecanto Hwy, Lecanto, FL
4. Downtown Brooksville Murals
Brooksville’s downtown is small but walkable, with colorful murals painted on buildings throughout the historic district.
The town has put together a self-guided mural and arts tour, which gives you a reason to wander the side streets and notice details you’d otherwise miss.
5. The Mermaid Trail (Scavenger Hunt)
Go on a search for mermaids? Sign me up! The Mermaid Tale Trail runs throughout Hernando County, with mermaid statues placed at various locations as a nod to nearby Weeki Wachee.
To date, there are 36 life-size mermaid statues that you can spot on your own scavenger hunt. You can win prizes through their Mermaid Tale Trail Passport, and you can grab a map of the trail from participating shops and businesses around town.
6. 1885 Brooksville Train Depot
The Train Depot has been in the same location since it was built in 1885 and it’s also worth a quick stop.
The museum is made up of four parts: the original ticket office, where passengers bought tickets and sent telegrams, a freight room with train artifacts and two HO model train exhibits, an enclosed dock with a 1925 LaFrance fire engine (the first fire engine ever purchased by the city of Brooksville), and a restored Cook Utility Box Car.
The boxcar has its own story. It was discovered abandoned in a swampy area southeast of Brooksville in Sumter County, hauled to the depot, and restored.
It originally belonged to Cummer Sons Cypress Lumber Company, which cut timber in the Green Swamp area. The car transported workers to job sites but also served as a mobile space for cooking, sleeping, office work, and machinery operations.
The depot sits at the start of the Good Neighbor Trail, a 10-mile paved path built on the old railroad track bed as part of the Rails to Trails program. That trail connects to the 46-mile Withlacoochee State Trail, one of Florida’s best rail trails for cyclists.
The depot is open on Fridays and Saturdays from noon to 3 pm. Admission: Adults $15, children 6-12 $7.
Address: 70 Russell St, Brooksville, FL
7. Sparacia Witherell Winery
I’ve been to a lot of small wineries in Florida, but Sparacia Witherell Winery quickly became one of my favorites.
It’s a family operation on 30 acres with a muscadine vineyard and tasting room that feels more like someone’s backyard than a commercial winery.
It really feels like family. Like home. And that’s what I love about it.
I really enjoy the pace here. You could easily spend an entire afternoon just vibing. There’s no rush and no crowds. You can enjoy a free wine tasting, purchase a bottle of wine, and then sit on the patio with a glass.
It’s a great place to hang out with family, friends, your significant other, or just enjoy some alone time. The bottles are reasonably priced, and I recommend taking a few home with you.
There is a good parking area. The winery is closed on Mondays and Tuesdays and opens at noon during the rest of the week.
If you’ve done the May-Stringer House tour and need somewhere to decompress, this is it.
Address: 21509 Snow Hill Rd, Brooksville, FL
Where to Eat in Brooksville
Florida Cracker Kitchen – This is where you start your day. I love having breakfast here! Good portions, great food, the smell of coffee and bacon the second you walk in. Get here early on weekends.
Coney Island Drive Inn – A must for Elvis fans! Elvis himself actually stopped at this diner for their famous footlong chili cheese dog during the filming of his movie Follow That Dream.
Great local spot for a light lunch or mid-afternoon milkshake. Classic American drive-in food served the way it used to be. Not trying to be retro. Just is.
Address: 1112 E Jefferson St, Brooksville, FL
Is Brooksville Worth Visiting?
Yes.
Brooksville is one of my picks for a Florida small-town getaway, especially if you want a mix of outdoor and off-the-beaten-path experiences.
Most small towns offer one or two things worth stopping for. But at Brooksville, you could easily spend a morning strolling downtown or visiting the historic sites, an afternoon at Weeki Wachee, spend the evening at a winery, and still feel like you didn’t see everything.
Not to mention, it’s in this small town in Florida where you’ll get to eat where Elvis ate 😊
Practical Info
How far is Brooksville from Tampa? About 50 miles north, roughly an hour by car depending on traffic.
How far is Brooksville from Orlando? About 75 miles west, roughly an hour and 15 minutes by car.
Best time to visit: Any time of year. Florida summers are hot and humid, which makes Weeki Wachee Springs a good place to cool off if you visit in summer. If you’re planning a late-night paranormal investigation at the May-Stringer House, book several months in advance.
How long do you need? A full day is ideal. You could squeeze it into a half day if you’re only doing one or two stops, but Brooksville rewards those who stay longer. Spend a weekend and enjoy the outdoors.
Frequently Asked Questions
Hey, I’m Yanitza 👋 Adventure Travel & U.S. Destination Specialist, travel writer, and hidden-gem hunter with over 8 years of experience helping travelers explore deeper and travel slower. I specialize in crafting authentic, stress-free adventures from small towns to scenic hikes and scuba dives. I’m a firm believer that the best stories happen when you venture beyond tourist hotspots. When I’m not planning getaways or writing travel guides, I’ll probably be home rewatching The Vampire Diaries like it’s my job and daydreaming about future adventures in Spain.