Explore Your City - Winter Garden


Winter Garden is my Stars Hollow. There may not be a literal town square, and it might be missing the quintessential small town diner reminiscent of Luke's, but there are plenty of other similarities that make it an unsuspecting gem.

While much of Orlando's urban sprawl spreads it's uninspiring strip malls into neighborhoods filled with neon E-cig signs and Wawa's, the core of Winter Garden has kept much of the vintage charm I got to enjoy as a child. In fact, it's charisma has increased.

Businesses are owned by people I know, and went to school with. The Mayor is the husband of the wonderful woman that was my second grade teacher. Outdoor patios and benches are filled with friendly faces, even if they are strangers.  But it's more than nostalgia and warmth that makes it a great place. It's transformed into a destination for people in Central Florida and beyond to explore.


The Plant Street Market has become the major gathering hub and with its two-year anniversary around the corner, we've already seen a bit of evolution in what greets guests along the busy corridor. Crooked Can Brewery is the main anchor in the back of the market with a brewery on site you can tour.  No matter what time of day you visit you are sure to see a patio full of happy beer drinkers and food enthusiasts enjoying the Florida sunshine under the natural shade of large oak trees. Inside variety is the name of the game with offerings including sushi, pizza, hot dogs, burgers, baked goods, healthy wraps, chocolates, popsicles, coffee, tea, and even a spot dedicated just to mac n' cheese.Michael's Ali Coal Fire Pizza serves up pizza with perfectly charred pieces of crust and fresh toppings that are served quickly from their oven.  Press'd Juice Bar is home to possibly the most beautiful acai bowls in the city, but beyond those bowls they have several healthy options for lunch including wraps, salads, soups, and of course freshly pressed juice and smoothies. For those sweltering days when you need a cool down treat, you can grab a Paleteriapop on your way out.


The market certainly isn't the only place to eat downtown, so you may need to pace yourself during your visit and practice your sharing skills.

As you walk down Plant Street you may not have BBQ on your mind, but that's the genius behind the open window of Harry & Larry's. The smell of smoked meat wafts out so passers-by cannot deny themselves. A brisket platter is plenty for two to split so you can keep on tasting what the town has to offer, but don't pass on the sweet potato wedges.


If BBQ isn't your thing, and you've already tried out the various fare at the market there is always Thai Blossom, Melts on Main Street for all things grilled cheese, and the Chef's Table at the Edgewater for a more upscale dining experience. The Deli Downtownrecently opened and The Whole Enchiladashould be opening at some point this year to add more ethnic flavors to the list.There are a lot of places to indulge your nagging sweet tooth in Winter Garden like Scoops Old-Fashioned Ice Cream and My Sweet JoJo Cafe but there's nothing quite likeMs. Bee's Popcorn. This charming shop has over 50 flavors of sweet and savoy kernels you can mix and match if you dare. Any place you can get flavors like dark chocolate sea salt & caramel mixed with dill pickle is alright with me.If carefully crafted chocolates are more in line with how you indulge, you won't want to miss a newer spot to downtown, Kaebisch Chocolate. Chef Anna Kaebisch brought her talent and worldly knowledge to Winter Garden about three months ago. This is Kaebisch's first shop in the US, following success in Brazil. In her shop you'll find delicately decorated chocolates, geltao, coffee, and decadent bars to take home. Half way through your exploration you may need another pick me up. While it's not quite Luke's, Axum does serve a great cup of coffee and serves as a homey spot to take an exploration break. Don't forget to take some side streets off the main drag so you don't miss other locally owned businesses. The Farmacy is a great alternative for picking up fresh, locally sourced produce, meats and dry goods. The great news is that if you enjoy what you find here, you can get your fix at their second location in the North Quarter Market in Orlando.


Not everything is food related in downtown Winter Garden. If you are looking to enjoy the outdoors you can rent bikes from one of bicycle shops and take a trip down the West Orange Trail. Or you can bring your little ones to enjoy the splash pad.If you aren't looking to break a sweat there are a few small cultural spots to visit. The Winter Garden Heritage Museumpreserves the history that gives the city its small town charm. The Railroad Museum chronicles the history of the two main railroads that ran through Winter Garden.For more arts and culture check out the SOBO Art Gallery. SOBO hosts workshops, lectures, and rotating exhibits. If you want to take in a live performance you can check out what's playing at the Garden Theatre. Be sure to check out their summer movie series.It's clear to see that if you haven't taken the time to explore Winter Garden it has so much to offer not just to the residents lucky enough to live within city limits, but for those of us in outlying places wanting a grab a piece of it's charm whenever possible.