Weekend Guide Exploring Brooksville, Florida

Located an hour North of Tampa, Florida, Brooksville isn’t the picturesque touristy beach town that comes to mind when you think of Florida. In fact, it doesn’t have a beach at all. What it lacks in giftshops selling t-shirts and shells, it makes up for in the serene, untouched forest and a deep history dating back to the 1800s. Slow down by spending a weekend exploring miles of hiking trails and historic homes, ending the day at the nearby vineyards. 

Chinsegut Hill Historic Site

Visiting the Chinsegut Hit Historic Site was the best $5 I’ve spent in a long time. As I dove up the narrow drive, the landscape unfolded into uncharacteristic hills for Florida. The canopy of arched trees blocked the view until I crested the hill opening into the manicured yard of the colossal white house comfortably sitting amongst the thick woods. 

Open on Saturday and Sunday, tours for the Chinsegut Hill Home start every half hour. The sprawling grounds are more than the beauty of the home, but the lives of all the people who lived there. Guides take you through an immersive history of the four families who owned the home until deeded over to the U.S Department of Agriculture in 1954. 


Although wealthy families built and inhabited the house, the tour does not shy away from educating visitors about the history of the enslaved people brought to this land in the 1840s. The original owner, Bird Pearson, acquired the land through the Armed Occupation Act to start his families homestead. The impacts of this Act incentivized people to inhabit the area by removing the Seminole Indians from their native lands. In exchange, homesteaders received five acres of land. As the land was cultivated and settled, the acreage of land increased, incentivizing the increase of enslaved people brought to the area during this time. Some of the enslaved worked for all four families, even after the Emancipation Proclamation in 1863; the tour highlights their stories. 

As time progressed, new families made Chinsegut home; most notable were Raymond and Margaret Robinson, who were heavily involved in progressive political causes during the early 1920s and 1930s. These political connections brought many famous visitors to the Chinsegut Hill estate; Thomas Edison, J.C. Penney, and Helen Keller are some of the most familiar names who spent time there.

Chinsegut Hill Historic Site in Brooksville, Florida. White house on a hill, surrounded by oak trees.
Chinsegut Hill Historic Site in Brooksville, Florida. In side the living room decorated with wooden furniture and a fireplace.

Hernando Heritage Museum 

The Hernando Heritage Museum Association is a collection of three separate museums: the May-Stringer House, the 1885 Brooksville Train Depot, and the Countryman One-Room Schoolhouse. During my afternoon wandering the brick streets of downtown Brooksville, I stumbled into the last tour of the May-Stringer House. From the street, the silver and scarlet Victorian era home looks like a life-size doll house. The lace-like trim, wrap-around porch, and steeply pointed roof made me feel like I was a character in one of the American Girl books I obsessively read in elementary school. 

The May-Stringer House is open Tuesday – Saturday from 11:00 a.m. – 3:00p.m, and tours begin every hour. The origin story of this home starts very similarly to the Chinsegut Hill Estate. The May-Stinger home was acquired through the Armed Occupation Act. The original footprint of this estate was a small four-room home. After the passing of the original owner John May, his widow Marena May remarried after the Civil War. She and her daughter would, unfortunately, die in the home. They would be buried in the family cemetery behind the house. These deaths have fueled rumors of the home being one of the most haunted homes in Florida. Visitors have said to have heard the crying of Marena through the halls looking for her baby. 

Several years later, the property was sold to Dr. Sheldon Stringer. He expanded the home’s footprint from four to fourteen rooms and added the Victorian details I admired on the house’s exterior. The estate was not just a family home but also served as the doctor’s medical practice for many years. Many of the rooms in the home today are dedicated to what the house would have looked like during Dr. Stringer’s time. 

May-Stringer House in Brooksville Florida. A large silver and red Victoria style home.
May-Stringer House in Brooksville Florida. Floral wall papered room with vintage panino.

The Olive Grove

One of my favorite things to do late at night is to scroll endlessly through Airbnb rentals. I came across The Olive Grove through one of their A-frame Airbnb listings, which led me to find their events’ Facebook page. They hosted their annual olive harvest event the weekend of my visit. A weekend-long celebration in September where visitors can learn how to grow olive trees in the Florida climate, infuse freshly pressed olive oil, and create clay oil lamps. 

The annual olive harvest event is one of many in the rotation of weekend activities. Pottery sessions and mosaics art classes are hosted at The Olive Grove to allow your creativity to flow under the protective arms of the property’s prominent oak trees. Local musicians and bands take the stage to provide entertainment for special and private events. If shopping is your favorite pastime, The Olive Grove store is open to purchase olives, olive oil, infused balsamic (if blueberry balsamic is in stock, you must try it), pickled vegetables, and homemade pasta. There’s something for everyone to enjoy. Remember to check their Facebook page for the most up-to-date upcoming events. 

The Olive Grove A-frame airbnb
A bottle of olive oil sold at The Olive Grove in Brooksville.

Citrus Wildlife Management Area – Dames Cave

In the rare instance Florida temperatures drop below 80°, take advantage of the opportunity to hike the trails in the Citrus Wildlife Management Area. Located 20-minutes North of Brooksville, this area of preserved Florida landscape includes nearly 50,000 acres to hike, horseback ride, hunt, fish, bike, or camp. The trails are well-maintained and clearly marked as you wander through the skyscraper-like pine trees. And the flat terrine makes exploring the area attainable for all hiking abilities. 

The trail that drew me into exploring the Citrus Wildlife Area was Dames Cave. I’ve never seen or been in a cave before (especially in Florida), and I couldn’t pass up the opportunity. The hike from my car to the cave was less than 10 minutes. I’m usually comfortable hiking alone; however, an eerie streak of nervousness overtook me when I arrived at the mouth of the cave. Warning alarms were going off in my head, and scenes from every scary movie I’d seen flashed before my eyes. As I slowly climbed down the narrow entrance, clinging to the slippery wet rocks, I let out a weak “Hello.” I didn’t hear an answer, and I wasn’t sure if that was good or if I just gave the monsters below time to prepare for my capture. Once at the bottom, I stood frozen to survey my surroundings. I didn’t see any snakes, bats, humans, or aliens, but I still had the overwhelming feeling of being watched. 


The term cave is used loosely here; it is more of a sinkhole. A one-room hole about a hundred feet below the surface. The floor was muddy, and water dripping from the ceiling echoed as it splashed into the puddles below. There were remnants of a small campfire and leftover beer cans scattered around the cave. I didn’t let my mind venture into thinking this was the opening scene of a horror movie. I just wanted to take a picture and get out of there. After packing my things back into my backpack, I heard voices approaching from above. Determined not to get trapped in this cave, I slung my bag over my shoulders and ran up the rocks like I was charging into battle. Leaping out of the entrance with a frazzled and wild look, I came face to face with three teenage kids, and at that moment, I realized I had become the monster I had feared just moments prior. 

Dames Cave. A women standing in a cave looking up towards the opening of the roof.

Bryant Manor Equestrian Center (Fairmile Farm)

One of my favorite television shows is the Paramount Network’s Yellowstone. With the new season starting in the coming weeks, I’ve been campaigning for my friends to watch it so I can talk to them about the crazy twist and turns that happen each week. One of my friends took the leap and started watching the show. Before I knew it, they were hooked, spending their weekend binging the first two seasons. 

Captivated by the mountain landscape and the central theme of cowboys on horseback managing the Dutton Ranch, my friend wanted to try their hand at horseback riding. This impulse is what led us to discover the Bryant Manor Equestrian Center. They offer a one-hour trail ride on their rescued racehorse around the property. The entrance to the property was a grand gate with Fairmile Farm boldly hanging over the entrance. As we drove up to the barn, cows and horses were organized into large pastures. The winding road eventually led us to the red barn at the far end of the property. After meeting with our trail guild and going over a few safety precautions, the horses were quickly saddled, and we slowly rode into the sunset. 


The horses were well-behaved as we rode through the pasture and past the group of resting bulls. On our way back to the barn, we detoured through a small pond and allowed the horses to graze on the aquatic plants. It was as refreshing for me to sit in the shade as for the horse to stand in the cool water. I was reminded of the power horses have as we sunk lower into the pond, eventually rising to the heels of my boots. 

I could have spent the entire day roaming around the farm. It reminds me of being a kid taking care of the cows, horses, and chickens I had growing up. After our horseback adventure, I  found Fairmile Farm’s Airbnb listing for a two-bedroom barn home. Guests have the option to work on the farm or simply enjoy the peaceful quiet of being in nature, away from the chaotic noise from the day to day. 


Strong Tower Vineyard & Winery

After a long day of crisscrossing Brooksville, settle in to watch the sunset at Strong Tower Vineyard & Winery. As I pulled up the drive, I thought google had made a mistake; this looked like someone’s house. Signs pointed me towards a large wooden door, where I found a gift shop and cases of wine surrounding me. I was stunned at the selection of 15 different types of wines offered in such a small place. The owner greeted me as I walked around, admiring the labels on the bottles. He was kind enough to brief me on the varieties of wines, ranging from heavy red wines to sweet dessert wines. I settled on a glass of Ison, a premium light-bodied red wine made from the delicious Ison grape. I took my glass to the outside seating area and enjoyed the day’s remaining hours under the pergola. 

Opened Wednesday – Sunday, the most exciting days to visit are Friday and Saturday. Food trucks, dancing, yoga classes, and special events are just a few of the lively events hosted on the weekends. Weekday visits are much more intimate, providing a remote place to sit and overlook the vineyard without interruption. 

Women in a dress standing in a vineyard. A glass on wine is being held up covering her face.
The entrance to the Strong Tower Vineyard & Winery. Outside you can see the seating area and chairs.

Exploring Brooksville was a surprise for someone who has lived close to the area for so long. There is so much history and culture living in this small town. I feel like I only scratched the surface. Big cities with fancy theme parks and trendy restaurants get most of the glory when people visit Florida. However, I encourage you to stop into the small towns along the way to discover what they have to offer. You might be surprised at what you will learn. 

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The information in this article was accurate when published but can change without notice. Please confirm rates and details when planning your trip by following the links in this article. If you find out-of-date or inaccurate information, I’d love to hear about it to update the article. Use the comments section below. Thanks! 

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