You’re in good company if you’re heading to the Sunshine State this winter. Leesburg, Florida, is a calm lakeside town in Central Florida that draws snowbirds with warm weather, friendly locals, and miles of shoreline. Its location near Lake Harris and its historic downtown make it an easy place to settle in for the season.
So come for a short escape. Or become a Florida snowbird staying all winter long. The area offers plenty of things to do in Leesburg, Florida, during snowbird season.
1. Explore Venetian Gardens on Lake Harris
Venetian Gardens is one of Leesburg’s most lively hubs. The park sits along the shores of Lake Harris with paved walking paths, fishing spots, photo-worthy bridges, and stunning water views. Locals take advantage of the scenic spot for peaceful morning walks, birdwatching, or relaxing by the water.
Start your day at Venetian Gardens with a morning stroll or light exercise. Here you can enjoy Florida’s mild winter months while taking in the scenic views before exploring more things to do in Leesburg, FL.
2. Visit Downtown Leesburg’s Local Shops & Historic Charm
Historic Downtown Leesburg is a place you can slow down and explore at your own pace. Main Street is lined with small boutiques, cozy cafés, and locally owned restaurants.
One stop worth making is Grandpa Joe’s Candy Shop. The nostalgic treasure is packed with thousands of sweets. From old-fashioned favorites to fun novelty treats, it’s an experience that brings out the kid in everyone. Step inside and you’ll feel a wave of nostalgia as you browse the colorful treats from decades past.
Continue down Main Street to see the iconic Tropic Theater. It’s a vintage landmark known for live shows and community events throughout the year.
3. Take Part In the Artwalk on 4th Street
The monthly 4th Street Live Artwalk in Downtown Leesburg is a favorite for snowbirds who enjoy meeting local creatives. On the second Friday of each month, the street transforms into an outdoor gallery with musicians, crafters, and painters set up along the sidewalks.
The family-friendly atmosphere is upbeat and inviting, and you can browse artwork or shop from vendors while enjoying the downtown setting.
Pro Tip: For art lovers looking for a memorable experience, stop by Myron Leggett Studio on the corner of 4th and Main Street. Leggett has spent more than 30 years painting intricate portraits in downtown Leesburg. You may catch him creating new pieces from his storefront window.
4. Eat at Great Chicago Fire Brewery & Tap Room
Head to Great Chicago Fire Brewery & Tap Room if you’re craving hearty Chicago-style pizza or a cold brew. The restaurant is a common gathering place for Midwestern snowbirds in Florida who enjoy familiar flavors during their stay.
The brewery also connects visitors to one of Leesburg’s biggest events each year – Leesburg BikeFest. The brewery’s lively atmosphere draws riders year-round. Monthly Bike Nights with Gator Harley Davidson bring out locals and seasonal visitors alike. Visitors enjoy a mix of food, conversation, and the energy of the local motorcycle scene.
5. Experience Leesburg Bikefest & Scenic Backroads
Leesburg Bikefest deserves its own spot on your list. The event is one of the largest in the region and brings thousands of riders into downtown each spring. The 2026 festival runs from Friday, April 24, through Sunday, April 26, filling downtown with three days of live music, bike shows, stunt performances, and hundreds of vendors.
The celebration stretches across more than 30 city blocks, creating an energy that snowbirds won’t want to miss before heading north for the season.
Even outside the event weekend, Leesburg has a strong and welcoming motorcycle community. Riders enjoy peaceful rural backroads that highlight prime real estate for open-road cruising. This part of Central Florida is a favorite for anyone who wants to take in the views from behind the handlebars.
Stay for Leesburg Bikefest & Save
Book RV sites starting at $62/night during the Central Florida motorcycle rally. Reserve your spot now at Holiday RV Park!
6. Join Local Recreation Activities
The Leesburg Recreation Department makes it easy for all age groups to stay active and connected in Leesburg, FL. Its programs focus on wellness, movement, and social connection while highlighting the best of local parks and community spaces.
Snowbirds appreciate the recreation programs for:
- Fitness & Wellness Options
- Seasonal Events & Community Activities
- Lifelong Learning & Hobby Workshops
- Access to Parks & Pet-Friendly Facilities
Snowbirds living in 55+ communities like Holiday RV Park and Lake Griffin Harbor Village enjoy all of that without leaving the community. These RV and manufactured home communities offer indoor and outdoor recreation, social events, and activities year-round. It makes it easy for snowbirds in Florida to enjoy retirement in a resort-style community.
7. Hit the Water: Boating on the Harris Chain of Lakes
Boating on the Harris Chain of Lakes is part of what makes Leesburg a favorite Florida destination. Visitors can rent a Pontoon boat, bring their own, or join a guided tour to experience life on the water. The Lakes’ calm shoreline, abundant wildlife, and open water make it a great setting for fishing, boating, or taking in the views.
Cruise over to Lake Harris Hideaway, a waterfront restaurant, and dock your boat for live music, drinks, and a bite to eat. With lake access in the community, guests and residents of Holiday RV Park and Lake Griffin Harbor Village can take advantage of lakeside restaurants and some of the best freshwater fishing spots in the region.
Why Florida Snowbirds Love Staying in Leesburg
Leesburg is often considered one of the most popular snowbird destinations in the United States. The atmosphere is friendly. The lifestyle is simple. And rentals in Florida are more affordable here than in many coastal areas.
Visitors can choose from a range of ways to stay that fit their lifestyle and budget. Holiday RV Park offers spacious RV sites and a relaxed setting that appeals to short-term and long-term snowbirds.
If a winter home in Florida is what you’re after, Lake Griffin Harbor Village provides a retirement community with manufactured homes just outside of Orlando, Florida.
Add Leesburg to your must-see list next time you’re in Florida. Leesburg offers the perfect balance of relaxation and activity, all in a place that feels like home.