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Winter Garden: A Charming City with a Juicy Past

Last Updated on August 17, 2023

Winter Garden, Florida, is a former citrus town incorporated in 1908. It is a beautiful, charming, and historic spot in Central Florida.

Large oak tree in a park

Located just west of the Orlando area on Lake Apopka, Winter Garden is known as the place “where good things grow”!

There are plenty of exciting activities and things to do in this part of the Sunshine State.

Winter Gardens Brick Clock Building

We’ve highlighted a few of our favorites.

Winter Garden Train Display at Central Florida Railroad Museum

Stop at the Visitor’s Center, the Winter Garden Heritage Museum, and the Central Florida Railroad Museum to dive deep into the history of West Orange County.

Things To Do In Winter Garden

Table of Contents

    The Historic Edgewater Hotel

    Edgewater Hotel Building Exterior

    This historic hotel and bet and breakfast first opened in 1927 and was one of the safest and most technologically advanced of its time.

    Originally, the hotel was primarily a winter hideaway for businessmen, housing for the Washington Senators during their Spring training and famous celebrities who visited Florida during the winter.

    Hotel front desk

    The hotel also housed the army during World War II in the 1940s.

    In the 1960s and 70s, it was home to the crews working on creating Walt Disney World.

    Room in Edgewater Hotel
    Source: Edgewater Hotel

    While the hotel closed its doors for a time, on November 8th, 2003, the Edgewater had a grand reopening after an extensive restoration.

    Today, the owners have kept as much of the original experience and ambiance as possible while providing modern comforts such as A/C, TV, and internet.

    However, you’ll still see antique sinks, fixtures, and even the original 1926 Otis Elevator.

    Dining room and wine display

    As a Bed & Breakfast hotel, guests are offered a full breakfast modeled after the original breakfast menu from 1926, served by the innkeeper each morning.

    Thai Blossom
    Source: Yelp

    The hotel also features a few great restaurants: The Thai Blossom (Thai cuisine), The Tasting Room (Tapas-style), and The Chef’s Table (fine dining).

    Scoops Old Fashioned Ice Cream at Edgewater Hotel in WInter Garden
    Source: Yelp

    Don’t miss Scoops Old Fashioned Ice Cream Store serving drinks, floats, and Hershey’s ice cream.

    Earl Brighams old-style Barbershop
    Source: Earl Brigham’s old-style Barbershop

    If you need a haircut, stop by Earl Brigham’s old-style Barbershop within the hotel. Earl has been Winter Garden’s beloved barber for over 50 years!

    Learn more about this historic hotel and book a stay on the Historic Edgewater Website!

    Edgewater Hotel Address: 99 W Plant St, Winter Garden, FL 34787

    The Garden Theatre

    The Garden Theatre exterior

    Originally built as a single-screen cinema in 1935, The Garden was the very first of its kind in Central Florida for “talkies” or talking pictures.

    The theatre quickly became a gathering place for the Winter Garden locals to watch newsreels and films of the day.

    The theatre’s interior was built in the Mediterranean Revival style, with a Spanish courtyard featuring Romeo & Juliet balconies, a Spanish tile roof, and a blue ceiling featuring stars.

    Garden Theatre
    Source: Garden Theatre

    Unfortunately, the theater closed in 1963. However, it reopened in 2008 through the efforts of the Winter Garden Heritage Foundation.

    It now showcases over 200 events per season and is a great spot to see live plays, concerts, movies, and more.

    This intimate venue has 295 seats, and some of its productions fill up quickly. We suggest booking your tickets in advance if you plan on seeing a show.

    Inside of the Garden Theatre
    Source: Garden Theatre

    Upcoming shows for the 2023 season include Every Brilliant Thing, Sweet Dreams: The Air Supply Musical, and Always… Patsy Cline.

    You can also check out their Movie Series, which includes classics and interactive favorites: pre-show games, trivia, sing-alongs, costume contests, and more.

    Learn more about The Garden Theatre and book your tickets on the Garen Theatre Website!

    Garden Theatre Address: 160 W Plant St, Winter Garden, FL 34787

    Plant Street Market

    Plant Street Market

    One of our favorite hot spots in Winter Garden is Plant Street Market. This local artisan community market features over 20 vendors selling everything from food and drinks to handmade products.

    While shopping and eating, you can enjoy live entertainment and a pet-friendly patio.

    The Crooked Can Brewing Company, founded in 2014, is attached to the end of the market.

    Sea animals made of bread

    Crooked Can is a brewery with a tap, tasting room, and brewery tours, created as a social gathering place for family and friends.

    Enjoy a craft beer or cider and their limited edition seasonal flavors.

    A few of our favorite spots inside the market include:

    • Axum Coffee
    • Wild Florida Honey
    • This Little Piggy
    • Sir Benji’s Donuts
    • Mac’d Out
    • Local Butcher & Market
    • Paleteria Popsicles

    Learn more about all Plant Street Market vendors on the Crooked Can website!

    Plant Street Market Address: 426 W Plant St, Winter Garden, FL 34787

    Winter Garden Farmers Market

    Winter Garden Farmers Market

    The Winter Garden Farmers’ Market has quickly grown into a community landmark. It’s in the heart of the beautiful downtown Winter Garden every Saturday from 8 am to 1 pm.

    Orchids

    There’s a large selection of vendors, from fresh baked goods, locally grown produce, flowers, homemade soaps, and live music. Grab a potpie to go or a fancy mango on a stick.

    Don’t forget to bring your friends (furry four-legged friends, too) and family to experience the Winter Garden Farmers’ Market. It’s one of the best in Florida.

    Cat wearing sunglasses

    Learn more about our favorite farmers’ markets in Florida by checking out: Nothing Beats A Fantastic Florida Farmers Market!

    Winter Garden Farmers Market Address: 104 S Lakeview Ave, Winter Garden, FL 34787

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