Historic Downtown Winter Garden

This past weekend we decided to skip our regular outing to one of the Walt Disney World parks and take a stroll through the historic downtown area of Winter Garden. This is a gorgeous area to visit, especially on a beautiful Florida afternoon. There are so many shops, cafes and restaurants along the brick paved main street that rolls right through the center of town.

Part of the West Orange rail trail runs right through the center of town, so you will often find bikers everywhere along the outside cafe tables enjoying a post bike ride latte or breakfast. Just be careful where you walk as we were almost run over by bike gangs at least twice.

Winter Garden rose up around the citrus growing boom in the late 19th century. A major rail road line went through the heart of Winter Garden carrying citrus produce throughout the state of Florida. In fact most of the buildings along Plant Street (the main strip through downtown) were built in the early 1900s and have amazing architectural details from that period.

Winter Garden is just west of Orlando and has been voted one of the best places in Florida to live, making it a fast growing suburb. In addition to Winter Garden Village, a major shopping destination with more mainstream chains and companies, downtown Winter Garden offers unique shopping and dining options. I thought I’ d share a few of my favorite spots in this beautiful downtown area.

I wouldn’t be a true Francophile if I didn’t mention Rosalie’s French Cafe first. This is one of the best French cafe’s I’ve ever visited. The decor inside is done in a charming French Country theme. They have a wonderful selection of teas, lattes, pastries and delicious lunch options.

It’s the perfect spot to meet up with a friend. On the weekends it does get packed so I recommend getting there on the earlier side, but it is worth the wait.

Right next door is the cutest shop called Adjectives. It’s the perfect place to browse and find gifts for everyone in your life. Seriously, this store has everything. From home decor to unique vintage items to even fashion, you are bound to find something for everyone on your list.

I found so many lovely vintage things in this store that I want for myself. I’m going to do a full review post of this store later on this week, so stay tuned!

Plant Street Market is a big hall full of different vendors. From tea shops, to macarons, to pizza and more. At one end is the Crooked Can Brewery. So browse through the hall and find your lunch option and then get a pint of locally brewed beer to enjoy it with.

There’s so many options in the Plant Street Market that I’m sure you will find something to satisfy everyone in your lunch group. Everyone can get what they want and reconvene at one of the outside tables to dine el fresco. My favorite place inside Plant Street Market is David Ramirez’s Chocolates

Not only does David Ramirez’s have amazing chocolate creations to enjoy but they have so many unique flavors of one of my favorite treats, MACARONS! David Ramirez is an Executive Pastry Chef who has worked in major cities in the US before settling in Florida. The pastries and artisanal chocolates are made fresh in house everyday. Perfect spot to grab a sweet treat after lunch.

I love the art deco feel of the Garden Theater’s facade. It harkens back to a simpler time. The theater was originally built in the 1930s and was the first place in Central Florida to view films with audio. It has been through several personas over the years, but in 2008 was redone as the theater it stands as today.

The theater boasts many cultural events, sometimes at least one a day. Everything from plays, musicals, live music and movies. One of my favorite moves, Billy Elliot, was turned into a musical which will be playing here soon. Got to get the tickets now!

Another favorite spot of mine is the fountain that sits in the middle of town in Centennial Plaza. Around the base is tile work featuring vintage citrus ads as a nod to the downtown area’s past. Canopies of wisteria border the fountain with porch swings. Its the perfect spot for that next Instagram post or just to sit and enjoy the sights and sounds of downtown Winter Garden as they whizz by on the rail trail.

There is a splash pad fountain near the city hall that kids love to run through and its perfect for cooling off on a hot Florida day, but I find the tranquility of this fountain more to my liking. And kids have a blast as well climbing around the fountains stone edging.

If you find yourself in the Orlando area with a day to spare, make sure to pop over to the historic downtown Winter Garden area. It is reminiscent of a time gone by and is the perfect example of the quintessential old Florida towns. There are so many more places to explore here and other shops I probably didn’t even get to see, so maybe I’ll have to do a Part Deux.

If you’ve visited downtown Winter Garden before, let me know below in the comments your favorite spot.

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