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Winter Garden: A Slice of Old-Florida

Winter Garden, about 20 minutes away from Central Florida’s famed theme parks in Orlando, is a superior slice of old-Florida. The brick lined streets and beautiful architecture exude small town charm, reminiscent of the way Florida used to be — before “The Mouse” moved in! In 1996 Historic Downtown Winter Garden was added to the National Registry of Historic Places. It encompasses nearly 100 acres, with 26 historic buildings.

This quaint little urban area is a former citrus town. And, although the groves have mostly been replaced with residential communities and popular retail developments, the history of this once bustling citrus hub is masterfully portrayed and well documented in the various Winter Garden museums.

Also, the award-winning West Orange Trail runs right through the middle of downtown Winter Garden. The paved 22-mile trail (converted railroad track) is a favorite of runners, rollerbladers, cyclists, and horseback riders.

 

 

Historic Winter Garden — Many Free Things To Do

One thing that surprised me was the amount of free things to do in downtown Winter Garden. Hubby and I spent a half day learning about the big-time history of this little-town, and mostly everything we did was free! That’s unheard of in Central Florida, the vacation capital of the world, where tourists tend to leave monumental amounts of money to experience the “magic” of the Sunshine State.

Read on to discover the best free things to do while in Winter Garden!

 

 

Central Florida Railroad Museum of Winter Garden

All aboard! No need to put-on your conductor’s hat to take this railroad tour. The railroad museum is housed in the old Tavares and Gulf Rail Company building. As you enter, through the old screen door, don’t forget to sign the guestbook to put your personal mark on history.

Inside the museum we were greeted by a volunteer, a railroad history buff that was eager to share his wealth of railroad knowledge. He offered to give us a personal guided tour of the museum, about an hour long, but because of time constraints we declined. The museum chronicles the history of the two main railroads that ran through Winter Garden, the Tavares and Gulf Rail Company and The Atlantic Coast Line. The building was jam-packed with railroad artifacts, some of which I had no clue what they were. But the helpful volunteer was always available to answer any questions.

I learned that the railroad was a vital component of the Winter Garden economy. In fact, it was its lifeblood. It imported passengers from all over the Sunshine State and exported produce and freight. The train even brought famous celebrities like Humphrey Bogart and Clark Gable to Winter Garden. Their lodging of choice was the distinguished and acclaimed Edgewater Hotel. They would go bass fishing on the local lakes and enjoy the rustic laid-back charm of Winter Garden to escape the Hollywood hype.

Some of the authentic railroad articles housed in the museum are rails and spikes used for building the tracks, scale models of trains from various parts of the United States, vintage dining car china, telegraph equipment, and an old 2-piece telephone.

The Central Florida Railroad Museum in downtown Winter Garden is located at 101 South Boyd Street and open every day from 1 – 5 PM, with free admission.

 

 

 

 

The Winter Garden Heritage Museum

Just as the name implies, this museum is dedicated to preserving the unique heritage of Winter Garden. Here, through the well preserved displays, you can take a walk down memory lane and peer into the past of this intriguing small town. The museum was built inside the 1918 Atlantic Coast Line Depot. And just like the other museums in Winter Garden, it’s staffed by local volunteers who donate their time.

In The Winter Garden Heritage Museum you’ll see vintage Winter Garden photography, documents from early settlers, a collection of Timucua Indian artifacts, early barber tools that were used at the Reeves Bros. Barber Shop (including the original red & white barber pole), vintage medical equipment, antique typewriter, an old telegraph, and a sizable collection of citrus crate labels. Additionally, many fishing-related items from Lake Apopka (5th largest lake in Florida) are on display like the turtle shell and alligator head.

In another room you’ll see photos of three old theaters in Winter Garden’s past, including the first Central Florida theater to show sound motion pictures (recently renovated and now called the Garden Theatre). One especially sentimental part of the museum is the section dedicated to local Winter Garden war heroes, with items donated by military veterans like the World War I helmet on display. All total, the Winter Garden Heritage Museum houses an extensive collection of over 5,000 artifacts documenting the area’s past.

The Winter Garden Heritage Museum is located at 1 North Main Street. It is open 7 days a week from 1 – 5 PM, and admission is free. You can’t miss the building, as it has a bright yellow caboose in front of it, which can also be accessed at no charge.

 

 

 

 

 

 

The Historic Edgewater Hotel

Okay, the Edgewater Hotel may not offer free rooms or dining, but you must at least walk into the lobby of this gorgeous hotel that was established in the roaring 20s (1927). It is free to look around. When you see the original wood countertops, antique sinks and fixtures, and fully operational 1926 Otis elevator at this Bed & Breakfast Style Inn, you’ll understand why this Winter Garden gem attracted Hollywood elite like Humphrey Bogart and Clark Gable.

The Edgewater Hotel has since been restored to emulate as much of the 1927 ambiance as possible, while adding modern conveniences like climate control, wireless internet, and gel-top bedding with memory foam. A full made-to-order breakfast is included with all rooms and served by the innkeeper.

And speaking of food, the Edgewater Hotel has three fantastic restaurants — Thai Blossom (serving lunch and dinner), The Tasting Room (serving lunch and dinner), and their signature fine dining restaurant called The Chef’s Table (open for dinner only). The Chef’s Table is one of my favorite restaurants, and worth the drive from almost anywhere in Central Florida. It’s quaint, intimate, and 5-star gourmet dining. It’s consistently rated one of America’s Top Restaurants, and the recipient of more awards than I can count. In fact, The Chef’s Table is where America’s Chef’s come to eat while in Florida! In my book, there’s no better Central Florida restaurant for a romantic rendezvous if you’re looking to impress that special someone with an added “wow factor.” (FYI — the Mushroom and Chive Crepe Torte appetizer with roasted shallot cream and truffle salt is to die for!)

 

 

 

 

The Winter Garden History Center

The Winter Garden History Center is where hubby and I began our tour of historic Winter Garden. It is home to the research library and archives of the Winter Garden Heritage Foundation. The files at the History Center are loaded with historical information, newspaper articles, photos, and maps.

If you’re a native of Winter Garden or have family ties to the region, you’ll find some interesting information here. Some of the collections consist of historical photographs, newspapers, local school yearbooks & memorabilia, and Native American artifacts. You can also learn about the movies and videos that were filmed in and around the Winter Garden area. (For more in-depth information, you can schedule an appointment to research the archives by calling 407-656-3244.)

The Winter Garden History Center is located at 101 South Boyd Street, East Annex Building (just behind the Railroad Museum). It is open Monday through Friday, 1 – 5 PM and is free to the public.

 

 

Plant Street Market

The Plant Street Market is kind of like a permanent farmer’s market. The brick building is full of unique vendors with an artistic flair. Some of the things you can find here are locally roasted coffee, cold pressed juice, farm-to-table food, hand-crafted chocolates, yumalicious (that’s my toddler grandson’s word for anything really, really good to eat) pastries, handmade apparel, creative jewelry, one-of-a-kind home decor items, handmade candles, essential oils, bath products, antiques, and an oxygen bar. Basically, the Plant Street Market has a little bit of everything!

The Plant Street Market is the perfect place to escape the hot Florida sun. Spend a balmy afternoon sampling different foods and drinks, and you can shop for a unique gift while you’re there. Sure, you’re likely to drop a few coins here if you choose, but once again, it costs nothing to look. And, if your timing is right, you may hit a specially hosted event including a festival or concert.

Also, at the far end of the Plant Street Market is the Crooked Can Brewing Company. Crooked Can is an authentic micro-brewery where you’ll be able to sample unique brews or take a tour to learn about the brewing process. But even if you don’t drink beer (like me) Crooked Can is connected to the artisan market with excellent pizza, sushi, burgers, wings, and vegan selections.

The Plant Street Market is located at 426 West Plant Street in Winter Garden, and open 7 days a week. You can check out the complete list of 20 vendors and take a virtual tour at the Plant Street Market website.

 

 

 

Winter Garden Florida — A Step Back In Time

Hubby and I truly enjoyed our visit to Winter Garden. Easing into the relaxing atmosphere was… quite easy! It’s a down-to-earth kind of place where the locals take pride in their small-town city, and stand ready and willing to share a story or two about its rich history. Much has changed since Winter Garden was built on the back of the citrus industry during the end of the 19th century, but a few things have remained the same, like the welcoming spirit of this Central Florida gem.

Winter Garden is the perfect spot to unwind from all the busyness and crowds that are synonymous with the greater Orlando area. As you stroll the red bricked streets it’s easy to forget you’re a short drive away from Disney and other world-famous Central Florida theme parks. But when you must return to the “Mouse” and his house, you’ll do so revived and energized by this brief reprieve.

Don’t forget to check out the Winter Garden Post for upcoming events and additional things to do, some of which are free as well!

 

 

QUESTION:  What’s your favorite thing to do in historic Winter Garden? Can you recommend another Florida town with a relaxed old-Florida atmosphere? Reply in the comment box below, our reader’s would love to know!