Winter Garden – Discover the History

Downtown Winter Garden is one of the most beautiful places in Central Florida.  We all know it as ‘Historic Downtown’ but understanding the incredible history of this great place is often overlooked.  Skip the trip out of town this weekend and spend some time discovering Winter Garden’s history with family and friends.  Here are a few of our favorite places downtown to connect with the rich history of Winter Garden.

Choo! Choo! Take a Trip to the Central Florida Railroad Museum

Located in the Tavares and Gulf Rail Company building downtown, the Central Florida Railroad Museum is fun for the whole family.  Stop in for a tour or browse at your leisure (We recommend the tour.  There are some very knowledgeable volunteer guides at the museum).

You’ll explore the early days of communication in the telegraph room.  You’ll hear stories of Clark Gable and Humphrey Bogart taking the train to Winter Garden for fishing trips. You can explore the Clinchfield Caboose. Bring your kids. Bring your parents.  There is something for everyone at the museum.

Open Daily from 1-5pm – Click HERE for more info

Catch a ‘Talkie’ at the Garden Theatre

Built in the 30’s, the Garden Theatre was the hot spot for locals to watch newsreels and was the first theatre in Central Florida to feature ‘talkies’.  Sadly, The Plant St. staple closed its doors in 1963 and became home to a supply store for a local farming company in Winter Garden.

Thanks to the efforts of the Winter Garden Heritage Society, the theatre was restored and reopened to the public in 2008.  It has since re-energized Historic Downtown Winter Garden with plays, concerts, movies and more!  You can now rent out the historical site for weddings, meetings, private movie screenings, and even ghost tours.

Click HERE for Events and more info

Hit the Winter Garden Heritage Museum

Whether we call it home or not, we know the historical significance of Winter Garden.  But there is so much more to this unique place that gives it the small-town charm it’s residents love.

Head over to the Heritage Museum and learn about early architecture and the local inventors who shaped the way we live every day.  Check out the Timucua Indian artifacts from their village along the shores of Lake Apopka.  Learn about the rich theatre history, world class fishing camps, and the local legends who proudly served our country.

The museum is open 1-5pm daily. Click HERE for more info or to Donate


The Clean Cans Team believes in community and spending time with family and friends.  Stop by these or any historic attractions on your way downtown to grab a bite at one of Winter Garden’s incredible restaurants.

Go out. Have fun. Don’t let summer chores stand in your way. (Like cleaning a grimy, sticky, smelly trash can). Let us do the dirty work!