15 Best Things to Do in Brooksville (FL)

Not far from the geographic center of Florida, Brooksville is an old city that goes back to a merger of two towns in the 1850s. Many cities with such a long past carry a lot of baggage, and Brooksville is no different.

I had a rewarding time delving into some of this history at the May-Stringer House, an historical museum, and the Chinsegut Historic Site, a former plantation at one of the highest points in Florida.

On the brighter side, modern Brooksville has an effervescent downtown right up my street, bubbling with events, against a backdrop of venerable buildings and mature live oaks.

A paved trail leads east right from the city into the pine and cypress woods of Withlacoochee State Forest, while there are contemporary restaurants, craft breweries, and family attractions to check out locally.

1. Downtown Brooksville

An interesting mix of old and new, Brooksville has all of the things people want from a 21st-century downtown. That means you can get around easily on foot, and there’s a concentration of local shops, culture, and service businesses.

When it comes to food there’s bistro cuisine, diner fare, elegant small plates to go with wine, Mexican, health food and Chinese.

At the very heart is a classic courthouse square, with the Hernando County Courthouse dating back to 1913. What I loved most of all were the spectacular old live oaks surrounding this building on all sides, with thick streams of Spanish moss.

2. Tom Varn Park

This sprawling public park is conveniently located just west of the center of town. With extensive woods and a cute pond with a lot of turtles, Tom Varn Park is a fine place to continue a stroll around Brooksville.

The park features a number of trails, including a 1.5-mile loop, served by covered pavilions for picnics. A playground, swings, and baseball diamond round out the park’s amenities.

Throughout the year, it hosts several fairs and festivals too. For me, the pick of them is the annual Art in the Park arts and crafts festival, which I’ll come to later.

3. May-Stringer House

This theatrical Victorian mansion on the east side of the downtown area is the home of the Hernando Heritage Museum. Dating back to 1855, the May-Stringer House has had many different owners and gained its current appearance in the late 19th century.

With 14 rooms, the house stands four stories tall, and is easily spotted for its gingerbread trim and triangular gables.

Several rooms inside have been decorated in period style, from a 1900s telegraph room to the Victorian bedrooms, 1800s doctor’s office and a stately dining room.

The collections encompass more than 10,000 items related to the county’s foundation, settlement, and development. You can visit Tuesday-Saturday, with docent-led tours on the hour.

Rumor has it that the house is one of the most haunted in Florida. For visitors more daring than me, evening ghost tours are available by appointment.

4. Withlacoochee State Forest

Brooksville borders Florida’s third-largest state forest, with almost 160,000 acres across a patchwork of district tracts in five different counties.

The largest within easy reach is the Croom Tract, which is arguably the most beautiful. Here you can make your way through 20,000 acres of longleaf pine and cypress woodlands.

The tract is crossed on its east side by the Withlacoochee River, so as well as hiking and bicycling, this is a fantastic place for canoeing and kayaking. As I’ll point out later, you can begin your adventure right in the middle of Brooksville.

The Good Neighbor Trail connects the city with the state forest along an old railbed, linking with the Withlacoochee State Trail near the riverbank.

5. 1885 Brooksville Train Depot

An exciting piece of history, this depot is the original one built in 1885 when the Florida Southern Railway reached Brooksville.

The complex is now a museum, one of three run by the Hernando Historical Museum Association.

Exploring the depot you can check out the ticket office, and the spacious freight room, loaded with railroad memorabilia, and artifacts from the tough early days of settlement in Hernando County.

The enclosed freight dock has a bell and siren for kids to ring, and contains a preserved 1925 LaFrance Fire Engine. Outside is an historic box car, salvaged from the swamps and pulled to this site.

Finally, I love how the railroad has been turned into a multi-use trail. From here you can hike or ride east to the state forest, where the trail connects with the 46-mile Withlacoochee State Trail.

6. Market 48 Brewing

Opened in the mid-2010s, this craft brewery in the west of Brooksville has a faithful following. Marker 48 Brewing is a pillar of the community, hosting all kinds of big events like Trunk or Treat in Halloween, and supporting worthy local causes with fundraisers.

Week to week there’s a lot happening at the taproom. When I took a look, this included an art class, karaoke, trivia, and of course a lot of live music.

As for the beverages, the brewery has gained a lot of recognition for its hard seltzers. A couple available at the time of writing were Mango, and Peach Papaya. Also look out for the weekly small-batch limited releases.

7. Chinsegut Hill Historic Site

Chinsegut Hill Museum — Chinsegut Hill Historic Site

Ten minutes north of downtown, Chinsegut Hill (269 ft) is one of the highest points in peninsular Florida. Capping the hill is a manor house in the Frame Vernacular style, built in the 1850s as part of a sugarcane plantation using enslaved people.

The property has had many uses over time, and is now a 114-acre preserve that can be visited on weekends.

For me guided tours are the best way to get an in-depth insight into the plantation, its history, and the lives of its various residents.

The museum’s permanent exhibits include historical artifacts and memorabilia, while there are also temporary exhibits on specific themes. On my visit, there was a display all about the 1920s, looking at Prohibition and the Christian revival in particular.

8. Boyett’s Grove & Citrus Attraction

An artifact of Hernando County’s citrus industry, Boyett’s Grove evolved into a visitor attraction after a freeze took out the orange crop in the 1960s.

This spot is a few things rolled into one, all with a charming dose of kitsch. There’s an aviary, a mini golf course, a giant gift shop/ice cream bar, and a dinosaur cave for kids.

For a taste of what came before, my time to be here is November through May for the citrus season.

At this time of year you can see an old-school orange grove in action, picking, washing, waxing and sorting its fruit as it did more than 60 years ago.

9. Brooksville Blueberry Festival

Brooksville is in one of the most prolific blueberry producing areas in Florida, so it’s natural that there should be a major celebration for this fruit.

This was previously a state event, but that was relocated to Kissimmee a few years before I visited. Now the festival lives on as a local event.

With more than 300 vendors, the Brooksville Blueberry Festival hits downtown Brooksville in late April when the weather is usually fabulous.

Music and arts & crafts are essential to the event of course, but blueberries take center stage at Blueberry Lane. Here you can indulge in all sorts of blueberry treats, from shortcake to wine, muffins, beer, breads, and blueberries themselves.

10. Sweetfields Farm

Out in the bucolic countryside in the south of Brooksville, this family owned and operated farm welcomes the public for seasonal events.

The big one is the Fall Season Event, which was happening when I was in town. From around late September into early November, this features a pumpkin patch, and a corn maze with a different design each year. There are also hayrides, barnyard animals, and a haystack playground.

Earlier in the year, springtime brings a spectacular sunflower maze, a slew of family activities, and bountiful fresh produce.

11. Hernando Oaks Golf and Country Club

The Sunshine State is the country’s premier golf destination. When many states are digging out from a cold and snowy winter, golfers in Florida are teeing-up.

The championship, semi-private course at the Hernando Oaks Golf and Country Club is Brooksville’s premier golf course. In a picture-perfect landscape of pine and live oaks, it plays just short of 7,000 yards from the blue tees.

In particular, I enjoyed the back nine at Hernando Oaks, which feels like you’re playing in a landscaped wilderness.

There’s a well-stocked pro shop at the clubhouse, as well as the Oak’s Grill, with a satisfying menu of burgers, flatbreads, sandwiches and salads.

12. Rising Sun Bistro and Market

The star of downtown Brooksville’s dining scene, Rising Sun Bistro and Market is an ever-popular destination.

On offer here is good food at reasonable prices in a comfortable, family-owned restaurant with a gentle country ambiance.

In an elegant old commercial building, the restaurant has ever-changing seasonal menus, with local ingredients where possible. For my part, I loved the brick oven pizza, and my app, which was fried green tomatoes with pimento.

They’re also particularly well-known for their coffee, which they source from local small-batch roasters and blend on-site.

13. Art in the Park

Out under the moss-draped oaks in Tom Varn Park there’s an art fair going back some 40 years now. Art in the Park takes place every March and cultivates an unpretentious feel.

I love this laid-back vibe, despite the high-quality art on show, and the considerable prize money.

You can check out the work of accomplished artists and crafters from all over the United States, displaying and selling everything from sculpture to ceramics, painting, jewelry, fiber art, and photography.

Thousands of people attend every year, while kids get the chance to be creative, there’s a county-wide student art show, and you can enjoy live music at spots all around the park.

14. Belle Parc RV Resort

For RV enthusiasts who happen to be 55 and older, the Belle Parc RV Resort is a great place to park up and relax while visiting Brooksville.

It’s in the name, but Belle Parc is more of a resort than a typical RV site. Among the amenities are a pool heated or cooled seasonally, as well as a fishing dock, hot tub, fitness center, TV room, tennis courts, pickleball and more.

The proximity to local attractions offers an abundance of activities. You can fill your schedule with biking, kayaking, and exploring the region’s many historical sites.

15. Brooksville Visitor Information Center

Another thing going for downtown Brooksville is the presence of the oak-shaded Hernando Park on the north side. Awaiting you here is Brooksville’s Adventure Coast Welcome Center.

A great place to start, this facility is staffed by knowledgeable and enthusiastic locals who know the area like the back of their hand. From here you can get a handle on Brooksville and Adventure Coast attractions, tours, restaurants, lodgings, and more.

Open during normal office hours, Monday to Saturday, the center is stocked with brochures, maps, guides and travel magazines.