Orlando, Florida, is a travel destination across the globe for the exciting attractions, lovable characters, and thrilling rides, but there is so much more to experience in Florida. If you venture just a few miles north of the amusement park, and just west of downtown Orlando is Clermont, Florida, a quaint town with rolling hills and a rich history of orange groves, farmland, and railroads, this is a beloved part of “true Florida.” If you’re up for a change from the frenzied commotion of International Drive, head a few miles north and see what Florida has to offer from the local’s point of view! This page has affiliate links and if you purchase something from this page I will receive a small commission at no cost to you. I donate 5% of this blog’s revenue to the Environmental Defense Fund, so you help donate to a great cause if you click on any affiliate links or ads that may be on this page!
Explore Downtown Winter Garden, Florida
Winter Garden, Florida is a quaint, historic strip of shops and restaurants. Plant Street is a picturesque cobblestone street lined with century old brick buildings that serve as shops and restaurants today. The town first began obtaining popularity after the Orange Belt Railroad made its way through neighboring town of Oakland in the mid 1880s and then the Tavares and Gulf Railroad in 1889, enabling Florida oranges to be easily transported north. The city incorporated in 1908 and many of the first buildings were built around this time, when it became a tourist destination in the 1930s, attracting Clark Gable, Errol Flynn and Humphry Bogart. Today its a well preserved piece of history that is frequented by Floridians throughout the year. Personally I’m enamored with the preserved history. If you take notice as you walk down Plant Street, there are many placards on the building toting the historical significance. There is a train museum that I still need to check out but can’t wait to make an afternoon for. There are beautiful parts of this little town that are perfect for pictures or just enjoying the afternoon. The West Orange Bike Trail is a historic path that runs right in the middle of this strip and is a beautiful part of town to explore and take pictures of, just make sure you don’t get run over by a cyclist 😉
Must Stop – Places to Eat in Downtown Winter Garden
There’s also amazing food at every turn, I can’t help but find myself constantly snacking. There is a local brewery and food hall that you cannot skip if you’re in the neighborhood. Crooked Can Brewing Company and Plant Street Market is one building that nestled amongst beautiful oak trees in a gorgeous historic looking building. Its actually a new building, but it has a charming feel like it belongs here for decades and fits right into this historic neighborhood. There is a beautiful serene outdoor eating area that makes you feel comfortable hanging out with a few brews and tasty treats. This phenomenal food hall is lined with vendors; my favorite is Sir Benji’s Donuts, they are prepared for you on the spot and there are about five different options to choose from.
If you’re hungry for a full meal and TexMex sounds appetizing (because when is it not?) please do yourself a favor and make your way to The Whole Enchilada. The enchiladas are obviously the rock stars here and you can’t go wrong with any of them, but my favorite is the Nacho Mama. Seriously look at those nachos. The margaritas are pretty bomb too and you can buy them by the pitcher if you feel like hanging out for a bit. Which you should do, because not only is the street view perfect for people watching, if you head upstairs, the rooftop is the perfect spot to sip margaritas, snack on some nachos and enjoy the chill vibes and Florida sun.
All of downtown Winter Garden is easily walkable and I highly encourage you set aside an afternoon to wander the town and take it all in… sights, food and beverages as well 🙂
Lakeridge Winery and Vineyard in Clermont, Florida
Just a few short miles north of Winter Garden and in Clermont, Florida is Lakeridge Winery and Vineyards. We weren’t expecting much when we were heading here (Florida isn’t really known for winery’s), but as you drive up you are greeted with gorgeous rolling acres of grape vines. Visitors are welcome to a free wine tour that leads you throughout the facility and allows you to sample Lakeridge’s premium wines. All of the wines were delicious, we actually liked more than we didn’t and we hadn’t planned on buying so many, but by the end of the visit, we had purchased six bottles! The prices are very reasonable, ranging mostly between $8 to $20 per bottle, and the more you buy, the more savings you get. With our six bottles, we received $6 off the purchase. I’ll be visiting frequently to grow my wine stock!
On Saturday and Sunday afternoons there are food trucks and live music outside in the vineyard from noon until 4:00. You can check the food truck schedule here. Visitors are welcome to purchase Lakeridge wine by the glass as well as beers, soft drinks and Lakeridge Cheese Trays. Bring your own blankets or chairs, play cornhole and enjoy the live music, vineyard views and beautiful Florida weather.
Southern Hill Farms in Clermont, Florida
Southern Hill Farms is, to give you a visual, just like walking into a fall festival in a Hallmark movie. Make sure you arrive early to ensure you can enjoy the fresh pick fields, depending on the season. The sunflowers are just gorgeous, I loved how beautiful all these flowers were sprawled on this hilly farm. Make sure you check Southern Hill Farm’s social media to see what is available before you go. There are plenty of options for lunch on the property, beer is sold as well. There are also usually activities for the kids, including a climbing wall. Strawberry donuts were sold when I was there as well so I had to grab a half dozen, they were so good! This farm is a must see for the family or just great way to spend a lazy afternoon at a picnic table, with some snacks and cool beverages amongst friends.
Luna Sea Alpaca Farm in Clermont, Florida
Just up the street from Lakeridge Winery is a cute, rustic little farm called Luna Sea Alpaca Farm, owned and operated by a sweet family that just loves their animals. Visitors can call King, the owner (352-223-9459) to schedule your visit for $10 per person. I never saw an alpaca before so this was a treat for me. We met the ducks, fed the chickens, and of course fed and pet the alpacas and llamas they have and learned all about them and the farm. Katy even got a little extra up close and personal with the llama with a little llama kiss. Watch the YouTube video linked below to see our day at Luna Sea!
There is an adorable little gift shop for all your llama memorabilia. Luna Sea also has yoga on Saturdays, which we’re excited to schedule soon!
I hope this post gave you some ideas to explore Orlando outside of the tourism, parks and chains. Orlando has some charming places that many people overlook. Have you been to any of these places? What did you think? Leave a comment below if you have any other favorite places in this part of Orlando!
