Are you looking for the best things to do in Leesburg, Florida?
No worries, I got you!
Coming back to Leesburg after all these years feels like stepping into a familiar dream with new colors.
This charming Central Florida gem nestled between sparkling lakes has evolved while keeping its small-town heart intact.
I grew up in this beautiful town, and I’m excited to showcase everything that it has to offer (or at least my favorite things to do).
So, let me guide you through the must-visit spots in my hometown that’ll make your trip unforgettable!
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Key Takeaways
- Venetian Gardens offers a serene environment perfect for relaxation, fishing, and enjoying nature.
- Ski Beach Bar and Grill is a popular spot for delicious food and waterfront views (a place that I MUST visit whenever I’m in town).
- Leesburg hosts vibrant special events throughout the year, including Bike Week and the Black Heritage Festival.
- Downtown Leesburg is a charming area to explore local shops, dining, and community culture.
- Unique attractions like the Burns Drugstore Speakeasy provide a glimpse into Leesburg’s historical charm.
Keep reading to see the amazing things that you can do in Leesburg, Florida!
1. Venetian Gardens
The crown jewel of Leesburg hasn’t lost its magic! Venetian Gardens offers breathtaking waterfront views that instantly transport you to a peaceful state of mind.
What makes it special? The winding boardwalks, lush landscaping, and the way the sunlight dances across Lake Harris at sunset.
I spent a lot of my childhood roaming the grounds of this beautiful place with my dad and my sister.
We’d fish here, climb trees, and just allow our imaginations to take us on magical adventures.
While you’re there, be sure to check out the Venetian Gardens Theater.
It’s a state-of-the-art auditorium with amazing views of Lake Harris, and in my opinion, one of the best things to do in Leesburg, Florida, for both locals and visitors.
HIPSTER POWER TIP: Visit on weekday mornings for the quietest experience – you might spot some local wildlife if you’re patient!
2. Ski Beach Bar and Grill
Nothing beats grabbing a cold drink while watching boats cruise by at this lakeside hangout.
The laid-back vibe at Ski Beach Bar and Grill in Leesburg, Florida, perfectly captures Leesburg’s easygoing spirit.
I love getting the Golden Fried Chicken Platter, but the Chicken N Waffles are still legendary. With the live music on weekends, it just feels like the perfect Florida hangout.
I recommend checking out the Florisiana dishes on the menu, like the Florisiana Boil.
It’s one of my favorites!
It comes with a full pound of shrimp or crawfish with red potatoes, corn, and andouille sausage served with melted butter and cocktail.
Honestly, I just love the whole vibe here!
The delicious food, great service, and the beautiful views of Lake Harris make it even better.
HIPSTER POWER TIP: Arrive before 5 pm to snag those coveted waterfront tables (especially on a wonderful Florida day) as they can fill up fast!
3. Special Events in the City
Leesburg knows how to throw a party!
The city’s calendar is always packed with community celebrations that showcase its vibrant culture, even as a small town here in Central Florida.
Bike Week
The rumble of motorcycles kicks off one of Leesburg’s most exciting events!
Drawing inspiration from the famous Daytona Beach Bike Week, Leesburg’s version brings its own unique charm and twist.
You can expect leather-clad riders, custom choppers, and street vendors for a fun festival atmosphere that feels like one big block party.
Even if you don’t ride, the people-watching is phenomenal with celebrity appearances, pro wrestling action, and epic headline bands, there’s plenty to see and do.
Black Heritage Festival
This powerful celebration honors Leesburg’s rich Black American history with music, food, and cultural displays.
The festival has grown tremendously, evolving over the past 20 years with gospel performances that will move you regardless of your beliefs.
I attended the very first festival when I was attending Leesburg High School and it was amazing. I even performed at that same festival as well.
It was a dream of my godfather, Pastor John Christian II, and former mayor of Leesburg, to bring such an amazing event to the community.
Leesburg’s Black Heritage Festival has blossomed into an incredible celebration, making it one of the best things to do in Leesburg, Florida!
4th of July
Leesburg goes all-out for Independence Day with a spectacular fireworks display over Lake Harris that rivals much larger cities.
I always try to get there a bit early since the family-friendly parades start early, and you definitely don’t want to miss them.
Then the fun goes on well into the evening for a booming Florida 4th of July night.
It’s one of the best events in Florida for the 4th of July and one that I have so many great memories from my childhood.
HIPSTER POWER TIP: Park at Venetian Gardens by 3 p.m. to avoid the traffic crunch later!
Christmas Parade
The holiday spirit shines bright during Leesburg’s Annual Christmas Parade!
Main Street transforms with twinkling lights and cheerful decorations at the beginning of December and the holiday season.
It always makes me feel like I have been placed directly into a romantic Hallmark Christmas movie.
4. Explore Downtown
Downtown Leesburg has undergone a remarkable renaissance while preserving its historic charm.
The brick-paved streets are lined with boutique shops, beautiful art galleries, and cozy cafés perfect for a Florida weekend getaway.
Then the streets come alive with vendors, music, and local artists for Second Fridays.
HIPSTER POWER TIP: Check out the hidden pond behind the main strip. This area is a peaceful spot to enjoy your coffee and a place my dad would take me and my sister frequently too after a day at the Leesburg Public Library!
5. Via Entertainment
When Florida’s afternoon showers hit, Via Entertainment saves the day!
This massive entertainment complex offers bowling, arcade games, and a surprisingly good restaurant located at the back end of the Lake Square Mall.
Don’t skip the laser tag arena, it’s a blast and always just as fun as I remember each time I go back and play.
Here are some fun things that you can do there:
- Arcade
- Axe-throwing
- Bowling
- Escape Rooms
- Go Karts
- Mini Golf
- Laser Tag
HIPSTER POWER TIP: Be sure to visit on Wednesdays as kids eat free from 4 p.m. until 8 p.m. and it’s half-off on all arcade games!
6. Rogers Park Splash Pad
You’ll be surprised to know that Leesburg has a Splash Pad area and is more like a mini water park!
Perfect for families, this refreshing oasis helps beat the Florida heat without the drive to the beach for the day.
It’s packed with creative water features that kids of all ages love to splash around in!
HIPSTER POWER TIP: There’s limited shade, so bring umbrellas and plenty of sunscreen!
7. Catch a Football or Basketball Game at Leesburg High School
There’s something magical about hometown high school sports!
The Yellow Jackets still bring the Leesburg community together with their competitive spirit.
The energy in the gym during basketball season is still electric after all of these years since my years of cheerleading at Leesburg High School.
Our basketball team even won the Florida State Championships in 2017 and in 2018.
HIPSTER POWER TIP: Be sure to proudly rock your Orange and Black to blend in with the passionate local fans!
8. Two Old Hags Wine Shoppe
Don’t let the quirky name fool you, as this charming wine bar offers sophisticated tastings in a relaxed, small-town setting.
One of my favorite things here at Two Old Hags Wine Shoppe is that their wine flights let you sample unique varieties you won’t find at chain stores.
HIPSTER POWER TIP: Tuesday and Friday evenings feature live acoustic music that perfectly complements the wine experience!
9. Donut King of Leesburg
This donut paradise remains a local institution for good reason! Their hand-crafted donuts put chain stores to shame.
The glazed and chocolate chip donuts still haunt my dreams in the best possible way, but their Castle Burgers always hit the spot if you’re looking to add a savory dish to your dessert feast.
Address: 708 S 14th St Leesburg, FL 34748
10. Leesburg Heritage Society and Historical Museum
Housed right off of Main Street, this museum offers fascinating glimpses into Leesburg’s past through artifacts and photographs.
You can check out exhibits that highlight the history of Leesburg, stretching all the way from 1857 right up to today!
11. Burns Drugstore Speakeasy in Marmaduke’s Lodge
This hidden gem combines history with mixology in a space that’s housed in the back of Marmaduke’s Lodge.
The craft cocktails, created by Katrina Atta, feature creative nods to Leesburg’s past that leans into its 1920s speakeasy aesthetic.
It’s a wonderfully delicious addition to this great city and one of the best things to do here in Leesburg, Florida.
Best Drinks on the Menu:
- Mai Tai
- Hurricane Katrina
- The Ol Pal
- Italian Dirty Martini
HIPSTER POWER TIP: The password changes weekly, so check their social media for hints or ask a friendly local!
HONORABLE MENTION: Leesburg African American Museum
This place is dear to me as it displays the history of the triumphs and struggles we’ve experienced here in Leesburg, Florida.
To come here, you’ll have to book an appointment in advanced for a private showing as the museum is still looking for a curator.
Please reach out to former Mayor, John Christian II, on this Facebook Page to set up a time to visit this historic destination!
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My Final Thoughts
Returning to Leesburg has been a journey of rediscovery, finding the perfect balance between nostalgic favorites and exciting new additions.
The town has grown up without losing its soul, and much like those of us who grew up here.
Whether you’re visiting for a day or staying longer, these authentic experiences will give you a true taste of this special corner of Central Florida.
Leesburg might not be the flashiest destination in Florida, but its genuine charm makes it worth the trip!
Until next time, Happy Florida Travels!
Contributors
About the Author
My name is NikkyJ. I’m a wife, a mother, a pharmacist turned theme park blogger, USA Today 10Best Contributor, and a writer who loves exploring all the hidden gems of Florida!
I was born and raised in Leesburg, Florida which attributes to my passion about for this amazing state.
I want to show you how you can create your own memories while discovering the Sunshine State!
Connect with me on Instagram!
About the Author
Sarah Jordan is a solo traveler enthusiast, professional travel writer, and proud mama to her rescue dog Coconut.
With a love for destinations across the globe, she made Epcot her first theme park and still treasures her EPCOT World Showcase passport to this day.
After finally following her inner wanderlust, she discovered the freedom and empowerment that solo travel brings.
