A Travel Guide to Winter Garden, Florida's Best Concerts & Events

Winter Garden, Florida, isn't just a charming historic town nestled on the shores of Lake Apopka—it is a vibrant cultural hub in West Orange County that comes alive with music, festivals, and community gatherings throughout the year. For locals and visitors alike, the historic downtown area, lined with brick streets and moss-draped oaks, serves as the perfect backdrop for some of Central Florida’s most beloved events. From the bustling weekly rhythms of the Farmers Market to the annual extravaganzas like the Music Fest, there is always a reason to gather a group and head to Plant Street.

At Charter Bus Rental Company Winter Garden, we know that the only thing harder than finding a parking spot in downtown Winter Garden on a Friday night is trying to coordinate a caravan of five different cars for a group outing. Whether you are a senior group from a nearby active living community, a corporate team looking for a night out at Crooked Can, or a wedding party enjoying the local nightlife, reliable transportation is key to enjoying these events stress-free. We have been serving the Winter Garden area for over 15 years, helping groups navigate the local event scene with comfort and ease. Let us handle the driving while you enjoy the show!

A few of the companies we’ve worked with

Experience the Rhythm at the Winter Garden Music Fest

One of the crown jewels of the local event calendar is the Winter Garden Music Fest. This annual event transforms the historic downtown district into a sprawling concert venue, with stages set up throughout the area featuring varied genres ranging from rock and blues to jazz and country. It is a massive draw for the community, often bringing in thousands of spectators who want to enjoy live performances, street performers, and local food vendors.

However, with road closures on Plant Street and thousands of attendees, parking becomes non-existent very quickly. The downtown parking garage on Tremaine Street fills up hours before the headliners take the stage. This is where Charter Bus Rental Company Winter Garden steps in. We can arrange a 56-passenger charter bus rental to drop your group off near the designated entry points, allowing you to bypass the circle-the-block parking game entirely. Your group can enjoy the music, sample food from the local vendors, and dance the night away, knowing that your air-conditioned motorcoach is waiting to take you home safely. We can even coordinate multi-bus shuttles for large community organizations or HOAs attending the festival together.

Saturdays at the Winter Garden Farmers Market

While not a traditional "concert," the Winter Garden Farmers Market is an event in its own right and has been voted the best in the nation multiple times. Every Saturday morning, the area around the downtown pavilion comes alive with live music on the stage, bustling crowds, and rows of vendors selling everything from organic produce to artisan crafts. It is a favorite weekly outing for garden clubs, senior centers, and tour groups.

Visiting the market with a large group can be tricky due to the sheer volume of foot traffic and limited parking. A private minibus rental is the perfect solution. We can drop your group off right by the entrance near the clock tower. One of the biggest advantages of taking a charter bus to the Farmers Market is the storage space! If your group plans on buying flats of strawberries, potted plants, or handcrafted furniture, you don’t have to worry about fitting it all in a sedan. Our buses come with spacious undercarriage storage bays perfect for hauling your market treasures back home. Plus, after a morning in the Florida sun, stepping into a cool, climate-controlled bus with reclining seats is the perfect way to end the outing.

Spring Fever in the Garden & Seasonal Parades

Winter Garden is famous for going big on seasonal celebrations. "Spring Fever in the Garden" is a massive festival that takes over the downtown area with chalk art, landscaping displays, and live entertainment. Similarly, the city's Halloween events and the incredibly popular Christmas Golf Cart Parade draw huge crowds lining the streets. These events are spectacular, but they also involve significant road closures and detours that can be confusing for out-of-town drivers.

When you book with Charter Bus Rental Company Winter Garden, you are hiring a driver who knows the local lay of the land. We stay updated on road closures along Dillard Street and Plant Street to ensure your group arrives as close to the action as possible without getting stuck in gridlock. For large family reunions or church groups attending these seasonal festivals, a charter bus keeps everyone together. You won’t have to worry about grandma walking six blocks from a remote parking lot or kids getting separated from the group. We provide door-to-event service that prioritizes safety and convenience.

Live Performances at the Garden Theatre

Located at 160 W Plant St, Winter Garden, FL 34787, the Garden Theatre is a beautifully restored historic venue that hosts plays, concerts, movies, and dance performances year-round. It is a cultural beacon for West Orange County. Whether you are a school teacher planning a field trip to see a matinee performance of a classic play or a group of theatre aficionados attending an evening concert, the Garden Theatre is a must-visit.

For school groups, our charter bus rentals offer a safe and reliable alternative to traditional yellow school buses. Our buses are equipped with seatbelts, DVD players (perfect for watching a movie related to the play you are about to see), and PA systems for teachers to make announcements. For adult groups attending evening shows, a minibus allows you to turn the night into a VIP experience. You can arrange for dinner at a nearby restaurant like Market to Table or Urban Coalhouse, and your driver will handle the logistics of moving the group from the restaurant to the theatre door. No need to worry about valet fees or walking in heels—we offer seamless curb-to-curb service.

Easy Access to Orlando’s Major Concert Arenas

While Winter Garden has its own charm, one of its biggest perks is its proximity to Orlando. Residents of Winter Garden frequently travel to the Kia Center (formerly the Amway Center) or Camping World Stadium for massive headliner concerts, NBA games, and major festivals. However, the drive down Highway 50 or the 408 during rush hour to get to a 7:00 PM show can be stressful, and parking in downtown Orlando is expensive and chaotic.

Charter Bus Rental Company Winter Garden makes attending big-city events easy for Winter Garden residents. Gather your neighborhood friends, your coworkers, or your social club and rent a party bus or charter bus for the night. You can start the pre-party on the bus with your own music playlist connecting to our sound systems via AUX or Bluetooth. You can enjoy beverages on board (provided everyone is of legal age), and let a driver handle the I-4 traffic. We will drop you off right near the arena entrance and pick you up when the encore is over. It turns a stressful commute into a fun extension of the concert experience.

Live Music and Brews at Crooked Can Brewing Company

Located inside the Plant Street Market (426 W Plant St, Winter Garden, FL 34787), Crooked Can Brewing Company is the heartbeat of Winter Garden’s social scene. With its sprawling outdoor patio, it is a prime spot for live music, trivia nights, and Oktoberfest celebrations. It is a favorite destination for bachelor and bachelorette parties, corporate happy hours, and birthday celebrations.

If you are planning a group outing involving alcohol, safety is the number one priority. By booking a shuttle bus or party bus with Charter Bus Rental Company Winter Garden, you automatically secure a designated driver for your entire group. Everyone can sample the award-winning craft brews and enjoy the live bands without worrying about how they will get back to their hotel or home. We can arrange a "brewery hop" itinerary that starts at Crooked Can and visits other local favorites, or simply provide a shuttle service for a corporate mixer. With our 18-passenger minibuses or larger coaches, we have the right size vehicle for any party size.

Why Choose a Charter Bus for Winter Garden Events?

Choosing a charter bus for events in Winter Garden isn't just about luxury—it's about logistics and comfort. The historic nature of downtown Winter Garden means that streets are often narrow, and while there are parking garages, they fill up rapidly during special events. When you drive separate cars, you risk members of your group arriving late, getting lost, or having to park miles away.

When you book with Charter Bus Rental Company Winter Garden, you are choosing efficiency. Our buses are equipped with modern amenities designed to make the Florida heat bearable. After standing at an outdoor concert or walking the Farmers Market, your group will be relieved to step into a cool bus with plush, reclining seats. You can share photos of the event instantly using our onboard WiFi, or simply rest your eyes while we handle the drive. We offer transparent pricing and a team dedicated to your schedule. We serve the entire region, from the luxury communities of Waterleigh and Hamlin to the historic districts, ensuring that no matter where your group originates, you travel in style.

Book Your Winter Garden Event Transportation Today!

Don't let traffic and parking logistics overshadow the fun of Winter Garden's incredible event lineup. Whether you are heading to the Music Fest, the Farmers Market, or a show at the Garden Theatre, Charter Bus Rental Company Winter Garden is ready to be your transportation partner. Our reservation specialists are available 24/7/365 to answer your questions, help you plan your itinerary, and provide a free, no-obligation quote.

We’ve helped everyone from local schools to Fortune 500 companies enjoy everything this city has to offer. We would love to earn your business and show you why we are the top choice for group travel in Central Florida. Call us today at 352-353-8690 to lock in your bus. Let's get your group on the road to a great time!

Frequently Asked Questions About Winter Garden Concert Transportation

Where do charter buses drop off in downtown Winter Garden?

Downtown Winter Garden has specific regulations regarding commercial vehicle traffic, especially during events like the Farmers Market or Music Fest when streets are closed. Generally, we coordinate drop-offs at safe, accessible locations near City Hall or designated loading zones on the perimeter of the event space (often near Dillard Street or Tremaine Street). Your driver will coordinate the exact pickup and drop-off points with you to ensure your group has the shortest walk possible while complying with city traffic laws.

How far in advance should we book a bus for the Winter Garden Music Fest?

The Winter Garden Music Fest is one of the busiest weekends of the year in West Orange County. Because demand for large vehicles spikes during major local festivals, we highly recommend booking your charter bus rental at least 3 to 6 months in advance. Booking early not only guarantees that you get the specific type of bus you want (like a party bus or a 56-passenger coach) but also helps you lock in the best possible rate before demand drives prices up.

Can you shuttle guests from Orlando hotels to a wedding in Winter Garden?

Absolutely! We specialize in wedding shuttle services. We can pick up your guests from hotels near Universal, Disney, or downtown Orlando and transport them to Winter Garden wedding venues such as the Heller Hall at the Winter Garden Heritage Foundation or Tanner Hall. We can run a continuous shuttle loop or provide a single trip to the ceremony and a return trip at the end of the night. We can also provide transportation to and from Orlando International Airport (MCO) for your out-of-town guests.