To most people, Brooksville is just a pit stop between Tampa and Ocala, but it’s a unique place to those who call it home. In addition to its historic downtown, Spanish oaks, and rolling hills, some of Brooksville’s character comes from its locally-owned restaurants serving fresh, homestyle food for generations.

You may think Brooksville would be lacking in dining options, but this small town has a surprising variety of eateries including lunchtime cafes, authentic Italian restaurants, and a roadside hot dog joint a celebrity once visited (keep reading to find out who it was!). You’ll also find a low-key pub and a Greek restaurant that also serves Cuban and Italian cuisines.

Next time you’re in the area, grab lunch at one of Brooksville’s favorite restaurants that have stood the test of time and see why the locals love them.

Coney Island Drive Inn

Established in 1960, Coney Island is a roadside hot dog joint reminiscent of yesteryear. This Brooksville institution is known for their world-famous foot-long hot dogs and equally impressive chicken wings. Enjoy either with a huge, thick-spoon milkshake inside Coney Island’s memorabilia-decked walls or outside near your car like in the good old days.

If you happen to dine inside, you’ll find plenty of Elvis pictures because The King himself actually ate at this restaurant in 1961! At the time, he was in North Central Florida filming his ninth movie Follow That Dream in nearby Inverness and just had to see what all the buzz in Brooksville was about!

Luigis Pizza of Brooksville

Brooksville’s oldest Italian restaurant, Luigi’s has been serving the area pizzas, pastas, and more in a warm, family atmosphere since 1970. You can’t go wrong with anything on their large menu, but Luigi’s savory calzones are a local favorite and definitely require a group effort to finish.

Red Mule Pub

Grab some drinks and enjoy good grub at the Red Mule Pub, Brooksville’s watering hole since 1978. This low-key spot is actually the only place in Florida where you’ll find a Chicago-style Vienna pastrami and corned beef sandwich, which is absolutely tasty and full of flavor. They also serve soups, salads, party trays, and sandwiches, including their signature Reuben. While waiting for your food, snack on free peanuts and play a game of “I Spy”- there’s plenty of hidden objects as the Red Mule is packed with memorabilia from wall to wall!

Papa Joe's Italian Restaurant

Forget Olive Garden, Papa Joe’s has been Brooksville’s premier fine dining restaurant since 1981! Its rich, authentic Italian dishes and upscale atmosphere are perfect for a number of occasions from family dinners to business meetings to romantic dates, especially during prom season. Papa Joe’s may look modern for a restaurant established in the 80s, but that’s because the original building burned down in 2014. Fortunately, the community rallied behind this beloved local business, and it quickly reopened with new, Tuscany-inspired interiors the following year.

Main Street Eatery

Everybody agrees: Main Street Eatery is the best place to grab lunch in Downtown Brooksville. This popular eatery has been serving locals homemade soups, salads, deli-style sandwiches, and desserts since its opening 1989. Not only is their food delicious, it’s also healthy because most of their meat is 98% fat-free and meals are served in perfectly-sized portions. In other words, you don’t have to feel guilty about getting their signature peanut butter pie for dessert!

However, it’s more than the food that has kept people coming back to Main Street Eatery for almost 30 years. For many, the eatery feels like home because of the staff’s friendly service and hospitality. “Our top priority is to make our customers feel like they are part of our family,” says Peggie Bell, owner of Main Street Eatery. “We pride ourselves in providing delicious, homemade food in a friendly, comfortable atmosphere. Come to Downtown Brooksville and have lunch with us!”

Main Street Eatery is just steps away from shops, art galleries, museums, murals, and historic homes, so you’ll definitely want to stroll through Downtown Brooksville before or after lunch. There is so much to see and do, but if you’re not sure where to start, just ask one of the servers at the eatery- they’ll be glad to tell you some great places nearby!

Mykonos II

Opened in 1993, Mykono’s II serves the best Greek food in Brooksville along with Italian and Cuban favorites. There are not many places where you can get spinach pie with garlic bread and a guava pastry, especially in such a casual, laid-back atmosphere.

Mallie Kylas Cafe

Located in the historic Hawkins House, Mallie Kyla’s has been a popular lunchtime spot in Brooksville since 1996. It’s the smallest restaurant in town with two small dining areas and a hallway in between, but Mallie Kyla’s is always packed with a line snaking through Westover’s, the adjoining decor, flower, and gift shop. This cozy cafe keeps customers coming back with their delectable soups, salads, and sandwiches as well as weekly specials like shrimp and grits on Wednesdays. If you have room for dessert, then you’re in luck because Mallie Kyla’s has the best cakes in town, hands down!

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Cafe' Masaryktown

Just off of FL-41 South, you’ll find a quaint, yellow two-story building brightening up the roadside in this little area outside of Brooksville called Masaryktown. In a seemingly humble setting, Cafe' Masaryktown boasts big flavor with their extensive menu featuring Cuban classics like empanadas, picadillo, and mojo pork. Although all of their entrees are appetizing, this cafe claims to have the best Cuban sandwich north of Habana, and we have to agree!

If Cafe' Masaryktown seems homier than other restaurants with its cozy, separating dining rooms, that’s because the building was originally established as the Masaryk Hotel and Restaurant in 1925 and was converted to the cafe years later in 1998. 

Whether you’re visiting or just passing through, you’ll definitely want to try these Brooksville restaurants and see for yourself why the locals have loved them for so many years.

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Cover photo courtesy of Chad Johnston