Winter Garden Downtown

By Damon Duvall
Tue, Nov 28, 2023 at 6:40AM

Winter Garden Downtown

Exploring Winter Garden Downtown: A Guide to Must-Visit Spots & Activities

Nestled amidst the picturesque landscapes of Central Florida, Winter Garden offers visitors a delightful blend of rich history, charming architecture, and vibrant culture. This enchanting city boasts a flourishing arts scene, delectable dining experiences, and a plethora of outdoor adventures in the Winter Garden downtown area. Whether you’re a history buff, a foodie, or simply seeking a relaxing getaway, Winter Garden has something for everyone. Get ready to be captivated by the charm and allure of this hidden gem.

Key Takeaways

  • Explore Historic Downtown Winter Garden, Plant Street & West Orange Trail for unique shopping and dining experiences.

  • Enjoy the abundance of fresh finds and local treasures at the Winter Garden Farmers Market.

  • Delve into the city’s rich history with visits to museums, sites listed on National Registry & outdoor activities such as birdwatching or exploring nearby theme parks.

Strolling Through Historic Downtown Winter Garden

Historic Downtown Winter Garden

Situated close to Winter Park, Winter Garden is celebrated for its connections to Florida’s citrus industry and rail transportation. Wandering through the historic downtown area unveils the city’s evolution from a former citrus town into a dynamic urban community.

Plant Street’s scenic beauty and West Orange Trail’s captivating landscape provide a snapshot of the city’s appealing past, serving as ideal locations to absorb Winter Garden’s abundant history and natural resources.

Plant Street Winter Garden

Plant Street provides a picturesque atmosphere with its historic structures, stores, and eateries, offering visitors a delightful experience in the heart of Winter Garden. With over 76 historical buildings spanning an area of 25 acres, Plant Street showcases a variety of architectural styles from 1912 and local vernacular architecture.

The street is home to a diverse selection of shops and restaurants, including Moon Cricket Grille, Thai Blossom Restaurant, and Three Birds Cafe, making it a true holiday wonderland for visitors.

West Orange Trail

The West Orange Trail, located in West Orange County, is a 250-mile Coast to Coast (C2C) Connector Trail that takes you on a scenic journey through Winter Garden’s beautiful landscape. Along the trail, you’ll find points of interest such as Killarney Station, Winter Garden Station, and the Renaissance Bike Trail, showcasing the city’s historical and natural assets.

The trail is perfect for walking, biking, and enjoying nature, as it is home to a wide array of flora and fauna, including lakes lined by trees, wildflowers, and various wildlife such as alligators and wading birds.

Shopping & Dining in Winter Garden Downtown

Winter Garden Village

Downtown Winter Garden offers a unique shopping experience with its quaint boutiques and specialty stores, making it an ideal destination for those looking to find one-of-a-kind treasures.

The city also boasts an impressive culinary scene, with highly recommended restaurants such as Caribbean Sunshine Bakery, Market To Table, and Taco Norteño, catering to a wide range of tastes and preferences.

Winter Garden Village

Winter Garden Village is an open-air shopping center boasting over one million square feet of stores and eateries, providing a diverse selection of shops to meet varied needs and interests. Some of the major stores available for shoppers include:

  • Target

  • Dillard’s

  • TJ Maxx

  • Bed Bath & Beyond

Dining options at Winter Garden Village range from Mexican to seafood cuisine, ensuring a delightful experience for all who visit.

Plant Street Market

Plant Street Market is a community hub that features 20 vendors offering organic eats and handmade products, making it a must-visit destination for foodies and art enthusiasts alike. With a range of delectable food options, such as craft beer from Crooked Can Brewery, specialty teas from AntiquiTEAs, and fresh meat from The Local Butcher and Market, visitors can indulge in a culinary adventure while browsing unique artisan goods.

Winter Garden Farmers Market: Fresh Finds & Local Treasures

Winter Garden Farmers Market

Taking place every Saturday morning, the Winter Garden Farmers Market, renowned as Florida’s leading Farmers Market, offers an abundance of fresh discoveries and local specialties. The market features:

  • A variety of locally grown produce

  • Baked goods

  • Specialty foods

  • Homemade soaps

  • Artisan creations

  • Fresh flowers

Visitors can enjoy an authentic taste of Winter Garden at this market.

Fresh Flowers & Baked Goods

At the Winter Garden Farmers Market, visitors can find a beautiful selection of fresh flowers, including attractive flower arrangements and bouquets.

Additionally, the market offers a variety of freshly baked goods, ranging from gluten-free options to various carb-based treats, ensuring that everyone can find something to satisfy their cravings.

Homemade Soaps & Handmade Products

The Winter Garden Farmers Market is also a haven for those seeking unique handmade products crafted by local artisans. With a wide array of homemade soaps and handcrafted goods, visitors can find the perfect souvenir to take home or a special gift for loved ones.

Delve into Winter Garden's Rich History

Winter Garden Heritage Museum

The abundant history of Winter Garden can be probed through visits to the Winter Garden Heritage Museum and several historically significant places listed on the National Registry. These sites offer a unique glimpse into the city’s past and its present-day preservation efforts, allowing visitors to gain a deeper appreciation for Winter Garden’s historical and cultural significance.

Winter Garden Heritage Museum

The Winter Garden Heritage Museum is dedicated to the preservation and dissemination of the city’s history, showcasing exhibits related to the citrus industry, local history, and the influence of the railroad on the region. Housed in the historic Atlantic Coast Line Railroad Depot, the museum features a collection of noteworthy artifacts and exhibits, providing visitors with an informative and engaging experience.

Historical Places & National Registry

Winter Garden is home to several historic places listed on the National Registry, emphasizing their historical and cultural worth and enhancing the city’s charm and quality of life. Notable examples of historic preservation in Winter Garden include the Winter Garden Heritage Museum, the Edgewater Hotel, and the Garden Theatre, all of which offer unique insights into the city’s past and present.

Arts, Entertainment, and Events in Downtown Winter Garden

Garden Theatre

Downtown Winter Garden serves as a nexus for arts, entertainment, and events, presenting a variety of engaging experiences for visitors. The historic Garden Theatre and live music performances at various venues throughout the city provide a lively atmosphere, ensuring that there is always something exciting happening in Winter Garden.

Garden Theatre

The Garden Theatre, located in Winter Garden, is a historic venue showcasing a variety of performances, including:

  • plays

  • musicals

  • concerts

  • comedy shows

  • movie screenings

With a rich history that began with the musical revue La Belle Paree, the theatre continues to entertain audiences with its diverse lineup of shows, making it a must-see attraction for arts and culture enthusiasts.

Live Music & Performances

In addition to the Garden Theatre, various venues throughout Downtown Winter Garden offer live music and performances for visitors to experience. From the popular ‘Fridays on the Plaza’ with live music every Friday night at Centennial Plaza Gazebo to the annual Winter Garden Heritage & Music Festival, there is always an opportunity to enjoy live entertainment in this charming city.

Outdoor Adventures in Winter Garden

Winter Garden presents a wide range of outdoor adventures for visitors, from wandering around the stunning Lake Apopka to unwinding in the city’s parks and green spaces, as well as exploring nearby theme parks. These natural attractions provide the perfect backdrop for a leisurely stroll, a family picnic, or a chance to reconnect with nature in the heart of Central Florida.

Beautiful Lake Apopka

Nestled close to Winter Garden, Lake Apopka is a picturesque lake that offers a serene retreat for visitors. Home to a wide array of avian species and various fish, including Largemouth Bass and Crappie, the lake is a popular spot for birdwatching and fishing.

With the Lake Apopka Wildlife Drive providing a scenic route through the area, visitors can immerse themselves in the natural beauty of this tranquil setting.

Parks & Green Spaces

Winter Garden’s parks and green spaces, such as Tucker Ranch Park & Nature Preserve and Chapin Station Park, offer the perfect settings for picnics and leisurely strolls. These tranquil spots are home to a diverse range of wildlife, providing habitats and resources for animals throughout the year, making them ideal locations for nature enthusiasts and families alike.

Practical Information for Your Visit

For a trouble-free visit to Downtown Winter Garden, it’s beneficial to acquaint yourself with the area’s transportation and parking options. From driving directions to public transit systems, there are various ways to access Winter Garden, ensuring a smooth and enjoyable experience for all visitors.

Getting to Downtown Winter Garden

Whether you prefer driving or utilizing public transportation, there are several options to get to Downtown Winter Garden. The Lynx buses provide regular trips throughout the city, while popular navigation apps like Waze and Moovit offer driving directions and step-by-step guidance from the nearest public transit station.

Winter Garden is approximately 25 miles away from Orlando International Airport, making it easily accessible for both domestic and international travelers.

Free Parking & Accessibility

When visiting Downtown Winter Garden, take advantage of the free parking options available, such as the Free Parking Garage at 160 S Boyd St, Joiner St parking at 25 E Joiner St, and Plant & Dillard parking at 114 E Plant St.

Additionally, Winter Garden is committed to being accessible for people with disabilities, with many event spaces and parking areas providing wheelchair accessibility and valet services.


Winter Garden offers a captivating blend of history, culture, and natural beauty that is sure to enchant visitors from all walks of life. From the charming streets of downtown to the serene landscapes of Lake Apopka, there is something for everyone to enjoy in this hidden gem of Central Florida. So why not plan a visit and discover the countless treasures that await you in Winter Garden?

Frequently Asked Questions

Is winter garden expensive?

Winter Garden is moderately expensive overall, with higher housing and grocery prices than the national average.

Is winter garden Florida worth visiting?

Winter Garden offers many recreational amenities, events and historical assets, making it a worthwhile destination to visit.

Is winter garden a town or city?

Winter Garden is a city, which has grown around small businesses and a thriving downtown area centered around Plant Street. It is listed on the National Registry of Historic Places and holds free events throughout the year.

Which is nicer Winter Park or winter garden Florida?

Winter Garden is an older community with a sense of history and tradition, while Winter Park provides the latest trends. Both cities offer something for everyone to enjoy.

What type of shops can be found in Historic Downtown Winter Garden?

Historic Downtown Winter Garden offers an array of shops, ranging from vintage boutiques to art galleries, providing a unique shopping experience for visitors and locals alike.

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