I lovingly refer to Downtown Winter Garden as our Stars Hollow. This downtown area is entirely walkable, featuring brick-paved roads and a picturesque "town center" known as Centennial Plaza. It is full of coffee shops, local boutiques, eateries, and museums that focus solely on the heritage and history of the area. The small-town feels are strong here, especially if you grew up in the area (for example, the Mayor is my 2nd-grade teacher's husband, and old schoolmates own several businesses). It's been interesting to witness its transformation from the 90s into the 2020s. Economic development has protected the historic elements of the city while also transforming and updating them to make it a destination that continues to receive press and accolades. Even if you have no ties to the area, you are sure to find it a charming place to visit once you've been there. Which begs the question, if you visit Downtown Winter Garden, what is there to do?

Plant Street Market

If you aren’t familiar with Plant Street Market, it’s become a destination within downtown Winter Garden, as the only food hall in the area. Complete with its local brewery as the anchor, Crooked Can, and several local food vendors, it’s a great spot to enjoy several tastes of the area.

Inside, you will find everything from BBQ, Pizza, sushi, healthy salads, baked goods, and meats to take home and cook yourself, all under one roof. Some of my favorites include Hunger Street Tacos, Norigami, and Michael Ali’s Coal Fired Pizza. The market itself also features a lovely outdoor space where you can enjoy the weather when it’s not sweltering, and the brewery hosts regular events.

Local Restaurants

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. There is a good mix of moderately priced dining options, along with a few higher-end celebratory spots, all within walking distance of downtown.

AJ’s Pizza is a great, casual but fun spot for pizza, and a newer addition to the dining scene, as is Soulshi. Be sure to walk down the side streets to avoid missing spots like Schweini's Delicatessen, an underrated daytime pub serving German-style sandwiches and beer.

Winter Garden also boasts four different coffee shops, but if you want to know my favorite, it’s Piccolo, which is located inside the Deli Downtown, another affordable spot for lunch.

Throughout downtown, a variety of casual and high-end spots can be found. Whether you are looking for a quick place to meet with friends or go out for dinner (Thai Blossom, Three Birds Cafe) or you are looking for a more celebratory atmosphere (Chef’s Table, Matthew’s Steakhouse), the options are plentiful.

Not to mention, just outside the border of downtown, there are several Authentic Mexican eateries to check out, like Don Poncho’s and Panaderia Mexicana Cardenas.

SHOPPING

The downtown Winter Garden shopping scene is small but plentiful, especially for women’s boutiques like Doxology, The Boutique on Plant, and Shoo Shoo Baby. Some other shops to check out:

Writer’s Block Book Store - known from their Winter Park location, their second shop is located on Plant Street filled with books and nifty gifts and accessories.
Swalty Sisters - A fun gift boutique that offers a wonderful mix of gifting items from popular trending items like Jellycats to a variety of items perfect for anyone you are shopping for.
Adjectives Market - A locally curated marketplace filled with art, home goods, apparel, and unique items.
Ruby + Rust - You might think it’s a plant shop when you first enter, but keep walking and you’ll find a lot of practical home goods and decor in this space. There will also be a new addition inside the shop soon of the return of Ms. Bee’s Popcorn, and old Winter Garden staple.
Southern Home Bakery - This local shop creates the cutest cookies for every occasion. They can be purchcased in their shop, and they also take custom orders.

Things to Do

Winter Garden Farmers Market

The award-winning Farmers Market in Downtown Winter Garden attracts people from all over Orlando, and with good reason. The market stalls sprawl out from the produce pavilion where local farmer Gardners Fresh piles perhaps the most extensive assortment of produce in any farmers market in Central Florida. If you're looking for organic produce, The Farmacy curates a mix of produce and proteins sourced from 20 local farmers in the area.

After you secure your produce, you can walk the rows of 100+ stalls of local artisans and makers, along with some hot food vendors. It takes place every Saturday from 8:00 a.m. to 1:00 p.m.

Parking in downtown Winter Garden is always free, and a parking garage is conveniently located right next to the market. Additionally, there is parking available throughout downtown, including other lots such as those on N. Boyd Street.

Arts + History

Not everything is food-related in downtown Winter Garden. If you are looking to enjoy the outdoors, you can rent bikes from one of the bicycle shops and take a trip down the West Orange Trail, or you can bring your little ones to enjoy the interactive fountain. If you aren't looking to break a sweat, there are a few small cultural spots to visit. The Winter Garden Heritage Museum preserves the history that gives the City its small-town charm. The Railroad Museum chronicles the history of the two central railroads that ran through Winter Garden. For more arts and culture, check out the SOBO Art Gallery. SOBO hosts workshops, lectures, and rotating exhibits. Currently, the Garden Theatre is closed; however, the City is utilizing the space for a Summer Movie Series, where every showing costs only $5 (this only lasts through the beginning of August).

Annual Events

One of the best things about Downtown Winter Garden is the annual events put on by the City every year. While most people are aware of their Holiday events, they also host a yearly Music Fest and the popular Spring Fever event. The best way to stay informed about these events is to follow their official social media accounts or visit their website at downtownwg.com.

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 to grab a piece of its charm whenever possible.

Things to do in Downtown Winter Garden