Does Winter Garden have a downtown? Absolutely, and it’s a perfect blend of old and new that you won’t want to miss. Picture a city where the charm of the past seamlessly intertwines with the vibrancy of the present.
A city where the echoes of a bygone era whisper through historic buildings, while the lively hum of a thriving downtown paints a vivid tableau of the present. Welcome to Winter Garden, a hidden gem in Florida, where history, culture, and adventure converge in a captivating symphony of experiences.
Discover Downtown Winter Garden, full of historic charm and exciting experiences.
Explore Plant Street for shopping, dining & nightlife plus the vibrant Plant Street Market.
Enjoy cultural delights such as live music & events, art galleries & studios or explore outdoors on West Orange Trail and Lake Apopka!
The enchanting heart of Winter Garden lies in the historic downtown area, a delightful getaway that transports you back in time. As you wander through the cobblestone streets, you’ll be greeted by the city’s small-town charm, evident in every nook and corner. From the stunning clock tower and pavilion to the artistically tiled water fountain, Historic Downtown Winter Garden is a testament to the city’s rich past.
By day, the downtown area buzzes with activity as locals and visitors roam the unique shops, museums, and art galleries. As the sun dips below the horizon, the city comes alive with a different kind of magic. The streets echo with the sound of applause from a live show at the Garden Theatre, while the scent of delicious cuisine wafts from the bustling restaurants. And if you’re lucky enough to be there on a Friday night, you’ll find yourself swaying to the rhythm of live music at the MoonCricket or at the Gazebo.
Venturing further into Winter Garden’s core, you’ll encounter Plant Street, the city’s primary artery. With a history as vibrant as its present, Plant Street is named after Henry Bradley Plant, a key figure in the development of Florida’s railroad system. Today, this street is a bustling hub of shopping, dining, and entertainment, reflecting Winter Garden’s successful transition from a rural train burg to a thriving community.
Throughout the year, Plant Street is the stage for a multitude of exciting events that paint the town with a festive spirit. Come December 1st, the street transforms into a sparkling wonderland for the annual Light Up Winter Garden event. If you’re a foodie, you’ll delight in the unique culinary experiences offered by the likes of Chef’s Table, a fine dining restaurant that’s a town favorite, located on Plant Street Winter Garden.
A leisurely walk down Plant Street is akin to a treasure hunt, with each turn unveiling a new gem to be found. From big names like Target, Best Buy, and Ulta Beauty to local boutiques and specialty stores, the shopping experience here is truly one of a kind.
Whether you’re on the prowl for the latest fashion or unique souvenirs, or merely enjoying some retail therapy, Plant Street caters to all. The Plant Street Market is a haven for shoppers, with about 20 vendors offering a diverse range of goods, from organic foods and artisan specialties to European-style baked goods and tropical ice pops. And for those with a penchant for vintage, the antique stores will certainly pique your interest.
After a day of shopping, there’s nothing better than indulging in a delicious meal, and Plant Street certainly doesn’t disappoint. From delightful pizza and sushi to succulent burgers and vegan fare, you’re spoilt for choice when it comes to dining options. For a more upscale dining experience, Chow Downtown, a vibrant section of Downtown Winter Garden, is home to award-winning restaurants.
As the night deepens, the city’s nightlife comes alive. Here are some popular spots to check out:
Pilars: an art-deco piano bar that sets the mood with its tantalizing martinis
The Attic Door: a wine bar with live music, offering a more laid-back vibe
Crooked Can Brewing Company: a must-visit for craft beer enthusiasts
At the heart of Plant Street, also known as Plant St, is the bustling Plant Street Market, a community hub that brings together local artisans and vendors. Open seven days a week, the market is a flurry of activity, with vendors offering everything from delicious organic eats at the plant kitchen to beautiful handmade products.
From fresh produce and tempting baked goods to distinctive keepsakes, the market caters to a wide variety of tastes. And if you’re lucky, you might even stumble upon a special event or market that adds an extra dash of excitement to your visit, such as a chef’s table experience.
Just when you think you’ve seen all that Winter Garden has to offer, the city surprises you with the Winter Garden Farmers Market. Held every Saturday from 9:00 AM to 2:00 PM, the farmers market is a vibrant showcase of the region’s agricultural bounty, with vendors offering:
fresh produce
baked goods
artisanal crafts
homemade jams and jellies
local honey
handmade soaps and candles
plants and flowers
gourmet coffee and tea
food trucks serving a variety of delicious meals
Make sure to visit the Winter Garden Farmers Market to experience the best of the local community and support local businesses.
But the farmers market is more than just a place to buy fresh goods. It’s a community event that brings together locals and visitors. As you browse the stalls, you’ll be serenaded by live music, while the kids have fun in the splash park. It’s the perfect way to spend a Saturday, immersing yourself in the local culture and community spirit.
Winter Garden’s allure extends beyond its rich history and vibrant downtown. The city is also a hub of arts and culture, offering a wealth of experiences that are sure to captivate any culture enthusiast. From the landmark Garden Theatre to a myriad of art galleries, the city’s cultural offerings are as varied as they are lively.
The city’s cultural offerings also extend to music, with live music events held regularly throughout the year. A vibrant music scene, various venues hosting live performances, and a variety of music events ensure that there’s always something for every music lover.
A prime asset in Winter Garden’s cultural realm is the Garden Theatre. Originally built in 1935 as a single-screen cinema, the Garden Theatre was the first theater in Central Florida built for ‘talkies’. Today, it stands as a beautifully restored historic venue, showcasing an array of exhilarating live performances such as:
plays
musicals
concerts
film screenings
The theatre’s stunning architecture adds to its charm, with features like its Art Deco-style facade, ornate detailing, and iconic marquee standing as a testament to its rich history. Whether you’re a theater enthusiast or just looking for a unique experience, a visit to the Garden Theatre is a must when in Winter Garden.
Music is an integral part of Winter Garden’s cultural tapestry, with live performances echoing through the streets all year round. Fridays on the Plaza and The Big Easy are among the wonderful live music venues where you can groove to the beat.
The city’s music scene is not limited to concerts. From music festivals and open mic nights to street performances and park events, there’s always something exciting happening. And if you’re lucky enough to be in town during one of the popular annual events like the Winter Garden Music Fest or Shop Small events, you’re in for a real treat.
In Winter Garden, art transcends the traditional boundaries of galleries and museums. The city is a canvas for local artists, whose works can be found not just in art galleries but also in public spaces, adding a dash of color and creativity to the cityscape.
Whether you’re an art connoisseur or a casual observer, the range of art forms represented in the city’s galleries is sure to captivate you. From bodily sculptures and botanical works to live or dried flower showcases, there’s something for everyone. And if you’re feeling inspired, there are numerous art studios offering workshops and classes, where you can unleash your creativity.
While Winter Garden’s lively present is unquestionably compelling, the city’s intriguing history is what truly distinguishes it. The Winter Garden Heritage Foundation and the city’s museums serve as time capsules, preserving the city’s rich history and providing a window into its past.
From its modest origins as a farming community focused on the citrus industry to its metamorphosis into a prosperous city, the museums and exhibits provide a panoramic perspective of Winter Garden’s historical voyage. Along the way, you’ll uncover stories of the city’s past, its people, and the events that shaped it into what it is today.
At the heart of Winter Garden’s preservation efforts is the Winter Garden Heritage Foundation. Founded in 1992, this non-profit organization is dedicated to preserving and celebrating the history and heritage of Winter Garden.
The foundation’s mission goes beyond maintaining the city’s historical landmarks. It also includes generating new possibilities for cultural and educational experiences. Over the years, the foundation has made significant strides in achieving these goals, successfully managing the History Research Center, the Central Florida Railroad Museum, and the Heritage Builder Award, among other accomplishments.
Another key player in preserving Winter Garden’s history is the Winter Garden Heritage Museum. Located in the heart of the city, near the Winter Garden Village, the museum houses an impressive collection of over 5,000 artifacts that document the area’s past, including a special area dedicated to local war heroes.
The museum’s exhibits span a wide range of topics, from the history of citrus farming in the area and the influence of the railroad on the community to the evolution of Winter Garden as a prosperous city. Whether you’re a history buff or just curious about the city’s past, a visit to the Winter Garden Heritage Museum is a must.
The preservation efforts of the Winter Garden Heritage Foundation and the wealth of information housed in the city’s museums all lead back to one place: Historic Downtown Winter Garden. Established in 1903, this section of the city serves as a proud reminder of Winter Garden’s successful preservation efforts.
Over the years, the downtown area has evolved from a farming community to a thriving city center, thanks to the city’s dedicated preservation efforts. Today, Historic Downtown Winter Garden is home to some of the city’s most treasured structures, like the Dillard building, one of the city’s oldest surviving structures.
Beyond its rich history and culture, Winter Garden also proffers a myriad of outdoor adventures. The West Orange Trail, a 22-mile path perfect for running, rollerblading, or biking, offers a fantastic way to explore the city and its surrounding areas, including Winter Garden FL.
There’s more to the trail than just a path for exercise. It’s also a gateway to the city’s natural beauty, with parks, playing fields, and a boardwalk leading to Lake Apopka along the trail. And for those with furry friends, the trail is pet-friendly, complete with a dog park for your four-legged companions to enjoy.
From its charming downtown and rich history to its vibrant arts scene and outdoor adventures, Winter Garden truly has something for everyone. Whether you’re indulging in retail therapy on Plant Street, soaking up the city’s history in its museums, or enjoying a leisurely bike ride on the West Orange Trail, every moment in Winter Garden is a testament to the city’s unique blend of the past and the present. So why wait? Come and experience the allure of Winter Garden for yourself.
Winter Garden is a thriving city located in western Orange County, Florida, part of the Orlando metropolitan area. It is renowned for its historic downtown area on Plant Street listed on the National Registry of Historic Places, as well as free high-profile events held throughout the year.
Winter Garden is a beautiful and entertaining destination, with plenty of recreational activities, events and historical sites to explore. It is definitely worth visiting!
Head to the Winter Garden Farmers Market every Saturday from 8:00 am - 1:00 pm and get your locally sourced goods!
Experience the best of Downtown Winter Garden with its unique shops, museums, live shows at the Garden Theatre, dining, and live music! Enjoy all this and more while making lasting memories.
407-575-5392
Wendy Morris LLC
DBA Wendy Morris Realty
Licensed in the State of Florida
BK 3146762
16797 Broadwater Avenue
Winter Garden, Florida 34787
