Once known for growing watermelons, this fast-growing city is wedged between two large bodies of freshwater, namely Lake Harris and Lake Griffin.
Leesburg’s exciting, culturally-rich downtown is a few steps from the shore of Lake Harris. On the waterfront here is one of my favorite parks in the world.
In the 1930s, the Works Progress Administration created Venetian Gardens, a series of enchanting islands joined by little bridges.
Lake Harris is also part of the Harris Chain of Lakes, the largest chain of lakes in Florida. From here you’ll have access to almost 80 square miles of freshwater, all linked by waterways.
1. Harris Chain of Lakes
Lake Harris is one link in the largest chain of lakes in Florida. Standing on the waterfront at Venetian Gardens, I’m always blown away by the notion that there’s’ more than 50,000 acres of freshwater waiting to be discovered from this very spot.
In the chain are Lakes Dora, Beauclair, Carlton, Eustis, Apopka, Griffin and Yale. All but one, Yale, are connected by navigable waterways. So the opportunities for adventure are almost endless.
For instance, you could set a course for the swimming spot at Horseshoe Island on Lake Harris. Or you could drop a line for largemouth bass, or spend the time island hopping, observing wildlife on the way.
2. Downtown Leesburg
In step with the city’s sharp growth since 2000, Leesburg’s downtown has blossomed as a place to shop, dine, and hang out.
There’s eye-catching street art, beautiful architecture, and an inviting streetscape, with palms, little gardens, and a beautiful plaza in front of City Hall on Main Street.
One of the many fine old buildings to check out are the Leesburg Opera House (1889), and the nearby Tropic Theatre. This opened as a B-movie house in 1932, and now serves as a stage for performing arts.
As a shopping destination, downtown Leesburg has more than its fair share of antiques stores, along with mom and pop stores for handmade gifts, collectibles, and homewares.
I’m always impressed by the dining scene, running the gamut from pub grub to seafood, pizza and steaks. Head a couple of blocks north and you’ll be at the picture-perfect Veterans Memorial Park on Fountain Lake, while the Venetian Gardens are a couple of minutes south.
3. Venetian Gardens
By Lake Harris and close to downtown is possibly my favorite spot in Leesburg. An inspiring example of a Depression-era WPA project, the Venetian Gardens were laid out in the 1930s.
Here there’s a network of beautiful little islands reached via ornamented footbridges. You can easily lose a couple of hours, roaming, taking in the views and appreciating the abundant birdlife and turtles.
Although this park is passive, there are recreation amenities close by. If you’re here with smaller kids, you’ve got the awesome Rogers Park Splash Pad on the west side.
Around the shore to the east is the Venetian Cove Marina where you can rent pontoons for a trip on the Harris Chain of Lakes.
4. Emeralda Marsh Conservation Area
On the northwestern shore of Lake Griffin, there’s another beautiful protected area offering a great outing from Leesburg.
A stop on the Great Florida Birding Trail, Emeralda Marsh Conservation Area covers more than 7,000 acres. This is my favorite local spot for wildlife watching.
The narrow levees are crossed by trails with distant views over the wetlands. At the driest time of year, from the third week of February to the end of May, you can also drive along the levees on a four-mile loop.
As with any wetland environment, the birdlife changes with the seasons. For example bobolinks flock to this place in the spring months, while migratory ducks and least bitterns stop by in fall and winter.
Whenever you come, you’re always likely to see wading birds like herons, egrets, ibises, roseate spoonbills, and sandhill cranes.
5. Leesburg Heritage Museum
If you’re looking for a time out from the lakes and waterways, one of my favorite spots is the local history museum.
The building is one of the grandest in the city, and constructed in 1922 for the Leesburg Woman’s Club. Over time this was the HQ for a host of businesses and organizations, including the library and the Chamber of Commerce.
It’s a fine place for newcomers to introduce themselves to Leesburg. Exhibits go into detail on the watermelon industry, which was big business up to the 1950s and was celebrated with an annual festival.
You can also find out about Leesburg landmarks like the Magnolia Hotel (1906), and the Lake View Hotel (1884) where famous figures like Annie Oakley would stay in winter.
6. Leesburg Center for the Arts
Based downtown, the Leesburg Center for the Arts was founded in 2000 to improve the quality of life in the city and Lake County. The center bills itself as a judgment-free ‘zone for art discovery, exploration, and experimentation.’
You can get a sense of the area’s art scene at the intimate gallery, which has a steady flow of exhibits all year. When I was around there was a compelling open show for textile and fabric art, with embroidery, weaving, cross-stitch and quilts.
The center also maintains a large-scale gallery at Plaza Lincoln, by the airport on US 441. As part of its commitment to community enrichment, there’s a ton of programs. Among them are classes in a wide array of skills to workshops, lectures, and open studios.
7. PEAR Park
This Lake County property in the south of Leesburg is divided between a large wildlife conservation area, and a smaller area for active recreation.
The land has an interesting past, as for more than 70 years from 1929 it was home to an experimental agricultural research station belonging to the University of Florida.
Small fragments from that facility remain, including the Orvel J. Walter Heritage Grape Arbor. There are more than six miles of trails, through habitats like freshwater marsh, scrub, pine flatwoods and longleaf pine sandhill.
Interpretive kiosks and pavilions will inform you about the park’s ecology, and there are a number of overlooks for wildlife spotting.
8. Pat Thomas Stadium
Since it was built in 1937, a long list of teams have called the Pat Thomas Stadium home. Found by the lake on the east side of Venetian Gardens, today this facility hosts Florida Collegiate Summer League games, as home field for the Leesburg Lightning, established in 2003.
In the past the stadium was the anchor for several minor and major league spring training camps, including the Phillies for more than 20 years up to 1968.
You can come to see Leesburg Lightning in action from the first week of June, with playoffs taking place in the last week of July. When I was in town the Lightning had just claimed their third FCSL championship.
9. Leesburg Art Festival
A wonderful showcase for artists from across Florida and the southeast, the Leesburg Art Festival has been an annual tradition for almost half a century now.
A two-day event, the festival takes place downtown on the first weekend in March. All along Main Street are scores of vendors, presenting everything from handmade jewelry to paintings, clothing, pottery, prints, photography, sculpture, and street art.
Something that really stood out to me was how much activity there was going on. I saw dancers collaborating with musicians, and numerous artists busy creating as the event took place.
Parents and kids can also get involved, at artmake stations, with tie-dying, pottery wheels, chalk art and much more.
10. Melon Patch Theatre
Leesburg has had a flourishing community theater group since 1951. Over the past 70+ years the Melon Patch Players have put on more than 400 productions.
Talent from across Central Florida comes together for professional-quality, musicals, comedies and dramas. The group’s permanent venue is an auditorium on the site of Leesburg’s first high school, donated in 1955.
Audiences are treated to five shows a season, while performers and crew get invaluable experience, on stage and backstage.
Along with the regular season, there are special events all year, including an annual haunted house at Halloween.
11. Haynes Creek Preserve
Near the west shore of Lake Eustis there’s a passive park encompassing a river island on Haynes Creek. Blount’s Island is at the core of the 36-acre Haynes Creek Preserve.
Now, the only difficult part is finding the entrance, which looked like a residential driveway when I stopped by.
But once you’re on the trail you’ll be in a seldom-visited pocket of wilderness, with spectacular live oaks and lots of wildlife sightings. I saw a handful of alligators on my short walk, as well as a majestic great egret.
12. Bourlay Historic Nature Park
On the edge of Lake Griffin, the Bourlay Historic Nature Park is also worthwhile if you’re interested in local heritage.
At the entrance to this parcel of pine flatwoods and hardwoods is an old Cracker-style house. A common type of frontier home built through the 19th century in Florida, this building was relocated to the park and serves as an informal visitor center.
It’s no coincidence that the building was moved here, as Bourlay Historic Nature Park is part of a tract settled in the mid-19th century by Leesburg’s first homesteader, Thomas Robertson.
From here you can set off and explore almost 90 acres of woods on blazed trails, with a scenic fishing pier pushing out onto the lake. My one tip is to douse yourself in bug spray as soon as you get out of the car.
13. Howey Mansion
Possibly the grandest residence in the area is a 20-room Mediterranean Revival mansion, completed in 1927.
Overlooking the peaceful waters of Lake Harris, the historic Howey Mansion was purchased by the current owners in 2017. They have been restoring the building since then, and have turned it into an upscale venue for weddings.
If you want a peek of this beautiful property you can put your name down for a guided tour. My Historical Tour took just over an hour.
As well as seeing the lakefront grounds and the progress on the restoration, I found out about William John Howey (1876-1938). One of the biggest citrus developers in Florida, he was founder and mayor of the surrounding town of Howey-In-The-Hills.
14. Flat Island Preserve
One of my most memorable hikes around Leesburg was Flat Island Preserve, jutting out from the north shore of Lake Denham.
This body of water sits just west of Lake harris. The island is reachable along a narrow isthmus, with a looping trail that takes in hardwood swamps, marshes, and upland hardwood hammocks.
The trail is bordered by beautiful saw palmettos, with long strands of Spanish moss draped from the live oaks overhead.
Including a lovely section of boardwalk, the trail is well-marked and is the result of more than 1,000 volunteer hours from the Florida Trail Association.
15. AMC Lake Square 12
Heading east along US 441, the Lake Square Mall had seen better days when I came through. There’s a pretty high vacancy rate here, but a few well-known retailers include Belk, PetSMart and Bath & Body Works.
To my mind, the main reason to plan a visit is for the modern AMC multiplex, which has all of the latest amenities. These include cozy recliners and stadium seating. In fact, it can be difficult staying awake throughout the movie in these seats.
There’s a MacGuffin’s Bar at this location, so you can enjoy an alcoholic beverage while you watch. Finally, keep an eye out for specials, one of which was 30% off matinees at the time of writing.