Winter Garden Historic District: Love at First Sight

Posted on: July 15th, 2019

By Kate Slentz

Established in 1903, the town of Winter Garden originally attracted citrus and vegetable farmers due to its locale on Lake Apopka. Eventually its business district grew between the two railroad lines that run through the city.

Edgewater Hotel

Today, Winter Garden’s Historic District serves as a successful example of historic preservation. Now located along the West Orange Trail (a 22-mile long multi-use rail trail), thousands of visitors patronize the shops and restaurants located in downtown Winter Garden, which is listed on the National Register of Historic Places.

My husband, Mike, and I recently made a day trip there to celebrate our wedding anniversary and fell in love with the downtown historic district. Known for the Garden Theatre and Edgewater Hotel, we found there was a lot more discover.

Our first stop was Winter Garden Wheel Works to investigate bicycle rentals but opted to save it for another time as it was unseasonably hot. We headed down the street a bit and strolled through the Winter Garden Farmers Market, which is open Saturdays from 9am – 2pm and features a large selection of vendors from locally grown produce and baked goods, to homemade soaps and fresh flowers, to home goods and clothing. We got some freshly blended (non-alcoholic) mango piña coladas from Mango Kings, which was very refreshing in the sweltering heat.

We then sought shade in the shops along brick-lined Plant Street. Some of my favorites included:

The Boutique on Plant

The Boutique on Plant, with a colorful and eclectic selection of women’s clothing and accessories; Adjectives Market, a collection of artisan-curated vignettes showcasing new and vintage furnishings, home décor, accessories and clothing (also with locations in Altamonte Springs and Winter Park); Driftwood Market, a great gift shop full of fun items including local art, home accessories and handmade treasures; and Ms. Bee’s Gourmet Popcorn and Candy Shoppe, which serves more than 70 different flavors of popcorn, vintage candies and gum, along with many varieties of homemade fudge.

Ready for some rest, we popped in Moon Cricket Grille for a cool drink and bite to eat. The eatery, established in 2003, is known for its selection of 99 bottles of craft beer. Customers who try all 99 get their name on the wall above the bar. However, I opted for the Mermosa – “a mimosa so big a mermaid could swim in it” – and drank it from a pint glass. We shared some yummy sweet potato fries before making our way to Plant Street Market.

Crooked Can Brewing Company

Anchored by Crooked Can Brewing Company, this community market includes 20 vendors selling natural, organic food and handmade products. We bellied up to the bar and ordered a pint (or two) from Crooked Can’s selection of craft beers brewed on-site. We took turns exploring the market and its food options such as BBQ at The Little Piggy; gourmet mac and cheese at MAC’d Out; coal-fired pizza from Michael’s Ali; pressed deli sandwiches at Butcher and Market; sushi from Jōdo; and made-to-order mini donuts from Sir Benji’s, among others.

Sir Benji’s, Plant Street Market

We ultimately splurged for the buffalo chicken mac and cheese from MAC’d Out, which was a generous portion featuring al dente pasta and gorgonzola as a twist. For dessert, we couldn’t resist the donuts from Sir Benji’s for several reasons (we love donuts and our son’s name is Benji). While best eaten hot and fresh, we did take some home to our son who loved them nonetheless!

There was much more we could have done and seen, but it was just the first of many planned trips back. Learn more about all the things to see and do at