Winter Garden is a charming town located just outside of Orlando, Florida. With its lively downtown, beautiful parks, and unique shops, there’s something for everyone to enjoy. Whether you are looking to spend time outdoors or enjoy delicious food, Winter Garden has plenty of fun activities for visitors and locals alike.
In this guide, we will be sharing some of the best things to do in Winter Garden. From scenic trails to lively festivals, there’s no shortage of fun experiences. Get ready to enjoy the natural beauty and warm community spirit that make Winter Garden a great place to be during any season!
Things To Do In Winter Garden
1. Watch a Show at the Garden Theatre
The Garden Theatre is a vibrant cultural venue in Winter Garden, Florida. It hosts a variety of performances, including plays and musicals throughout the year. This historic theatre has a charming atmosphere that enhances each experience.
Attending a show here is a great way to immerse yourself in local art. From dramas to comedies, there’s always something captivating happening on stage. The talented actors and production teams consistently deliver high-quality performances.
The theatre is a beautiful building with an intimate setting. This unique layout allows every seat to offer a great view. You can feel the energy and excitement from the audience and performers alike.
Before or after the show, consider enjoying a meal at one of the nearby restaurants. Many dining options are within walking distance. This makes it easy to extend your evening into a delightful outing.
A visit to the Garden Theatre is a must for art lovers. It truly showcases Winter Garden’s commitment to the arts while providing entertainment for all ages.
Address: 160 West Plant Street, Winter Garden, FL 34787.
2. Visit the Winter Garden Farmers Market
The Winter Garden Farmers Market is a lively hub of activity every Saturday morning. This market brings together local farmers, artisans, and vendors to create a delightful shopping experience. It’s a perfect spot to find fresh produce, baked goods, and crafts.
Strolling through the market is a treat for the senses. You can sample juicy fruits, colorful vegetables, and homemade treats. Take your time to chat with the friendly vendors and learn about their offerings.
The atmosphere is vibrant and full of energy. Live music often fills the air, making it a great outing for families. Kids can enjoy special activities while parents explore the diverse stalls.
Besides shopping, consider relaxing in the nearby parks with a picnic. You can grab a few goodies from the market and enjoy them in a beautiful setting. It’s a lovely way to wind down your morning.
The Winter Garden Farmers Market is not just about shopping; it’s about community. This local tradition connects residents and visitors in a celebration of freshness and creativity.
Address: Downtown Pavilion, 104 S. Lakeview Ave, Winter Garden, FL 34787.
3. Explore Art at SOBO Gallery
SOBO Gallery is a must-visit for art enthusiasts in Winter Garden. It showcases local artists, offering a platform for a variety of art forms. From paintings to sculptures, there’s always something new and interesting to see.
The gallery hosts rotating exhibitions, ensuring each visit presents fresh perspectives. Many pieces are for sale, allowing visitors to take home a piece of local culture. This creates a unique opportunity to support artists directly.
In addition to visual art, SOBO Gallery offers classes and workshops. These sessions allow you to unleash your creativity under the guidance of talented instructors. It’s a fun way to engage with art in a hands-on manner.
The welcoming atmosphere makes it an enjoyable place to spend time. Whether you’re an art expert or a curious learner, there’s something for everyone. The staff provides insight and stories about the artists and their works.
Visiting SOBO Gallery is more than just looking at art; it’s about connecting with the local art community. You’ll leave inspired and appreciating the vibrant culture of Winter Garden.
Address: 108 S. Park Ave, Winter Garden, FL 34787.
4. Discover History at the Central Florida Railroad Museum
The Central Florida Railroad Museum invites you to step back in time. This small but engaging museum showcases the rich history of railroads in the area. You can explore various artifacts and exhibits that tell the story of the railway’s impact on the region.
Fascinating displays include old photographs, model trains, and historical documents. Each exhibit offers a glimpse into the life of railroad workers and the significance of trains in connecting communities.
The museum is housed in a historic train depot, adding to its charm. Walking through the depot, you can feel the nostalgia of days gone by. It’s a perfect stop for history buffs or anyone curious about the area’s past.
Guided tours provide in-depth information, enhancing your visit. Knowledgeable volunteers share stories that bring the exhibits to life. You can ask questions and learn more about the fascinating history of trains.
A visit to the Central Florida Railroad Museum enriches your understanding of Winter Garden. It’s a unique journey through time that you won’t want to miss.
Address: 1014 N. Park Ave, Winter Garden, FL 34787.
5. Enjoy Craft Brews at Plant St. Market
Plant St. Market is the perfect destination for craft beer lovers. This vibrant marketplace offers a unique selection of local brews and artisan food. You can relax in a friendly outdoor atmosphere while enjoying live music on weekends.
The market features a variety of food vendors, each offering delicious dishes. Pair your craft beer with gourmet bites for a delightful experience. It’s an excellent place to try something new and support local businesses.
Engaging with the community is easy here. The outdoor setting invites conversation, making it a great spot to meet friends or make new ones. The lively atmosphere keeps energy high throughout the day.
Seasonal events and pop-up markets add excitement to your visit. Enjoying live entertainment in this dynamic setting enhances the overall experience. There’s always something happening at Plant St. Market.
Whether for a casual lunch or a lively evening with friends, Plant St. Market is a must-visit. It showcases Winter Garden’s vibrant food and craft beer culture.
Address: 426 W. Plant St, Winter Garden, FL 34787.
6. Bike on the West Orange Trail
The West Orange Trail is a cycling paradise in Winter Garden. This 22-mile paved trail winds through picturesque landscapes. It’s perfect for biking, walking, and even jogging, making it a popular spot for outdoor enthusiasts.
The trail is well-maintained and easily accessible from multiple points throughout Winter Garden. Whether you’re a seasoned cyclist or a family looking for a leisurely ride, the trail accommodates everyone.
Along the route, you can enjoy beautiful views of nature. The surrounding trees, lakes, and wildlife offer a refreshing escape from the hustle and bustle. It’s a great way to stay active while experiencing the area’s natural beauty.
There are plenty of rest areas and picnic spots if you wish to take a break. Enjoy a snack or have a mini picnic before continuing your adventure. The trail is perfect for a day out with friends or family.
Biking on the West Orange Trail is more than just exercise; it’s a chance to connect with nature. It’s one of the many gems that make Winter Garden a delightful destination.
Starting Point: Multiple access points in Winter Garden.
7. Learn at the Winter Garden Heritage Museum
The Winter Garden Heritage Museum offers a fascinating look into the local history. Situated in a beautifully restored citrus packing house, this museum showcases the city’s rich agricultural past. You’ll find engaging displays and artifacts related to the area’s history.
Each exhibit provides a story that connects you with Winter Garden’s roots. You’ll learn about the citrus industry, transportation, and the growth of the town. The stories shared paint a vivid picture of what life was like in earlier times.
The museum often hosts special events and educational programs for visitors of all ages. These programs dive deeper into different aspects of local history, making learning fun and interactive. It’s a great place for families to explore together.
The knowledgeable staff is always happy to share insights and additional information. Their passion for history is contagious, helping you appreciate the rich heritage of Winter Garden.
A visit to the Winter Garden Heritage Museum is both educational and enjoyable. It’s a perfect way to connect with the community and learn about its marvelous history.
Address: 1 N. Boyd St, Winter Garden, FL 34787.
8. Attend Fridays on the Plaza
Fridays on the Plaza is a popular weekly event in Winter Garden. Every Friday evening, the Centennial Plaza comes alive with music and festivities. This event is a great way to kick off the weekend with family and friends.
Local musicians provide lively entertainment, creating a festive atmosphere. You can dance, relax, or simply enjoy the sounds of different genres. It’s a wonderful opportunity to discover local talent.
The plaza is often filled with food vendors offering delicious treats. Grab a bite to eat while you listen to the music or participate in various activities. There’s always something happening that invites community engagement.
People of all ages come together to enjoy the night. It’s a perfect time to unwind, socialize, and make memories with loved ones. The relaxed and welcoming vibe makes it a favorite weekly gathering.
Attending Fridays on the Plaza is a highlight of the week for many. It encapsulates the spirit of Winter Garden and the joy of community.
Location: Centennial Plaza.
9. Shop, Dine & Stroll with Live Music
Shopping, dining, and live music come together beautifully in Downtown Winter Garden. Every Saturday, the streets transform into a bustling market filled with unique shops and delicious restaurants. This combination makes for an enjoyable outing.
As you stroll through the area, you’ll find boutiques offering handmade crafts, clothing, and more. Supporting local businesses is rewarding and helps maintain the community’s charm. You’ll likely find the perfect souvenir or gift.
With live music playing in the background, the atmosphere is lively and uplifting. Enjoying performances while you shop or dine enhances the experience. It’s common to see families, couples, and friends enjoying their day out together.
Numerous dining options allow visitors to explore various cuisines. From cozy cafes to fine dining, you can treat yourself to a lovely meal. No matter what you choose, the food scene is sure to impress.
Shopping and dining in Downtown Winter Garden is more than just errands; it’s an experience. The combination of activity and entertainment creates a memorable outing.
Location: Downtown Winter Garden.
10. Visit the Winter Garden Village
Winter Garden Village is an expansive shopping area that caters to every need. With a mix of stores, restaurants, and entertainment, it’s a go-to destination for locals and visitors alike. From fashion to home goods, you’ll find a great selection of shops.
The village offers a relaxed shopping experience with a beautifully designed outdoor layout. You can comfortably walk from store to store while enjoying the Florida weather. This makes for a pleasant shopping trip without the stress of crowded malls.
Numerous dining options allow you to refuel during your shopping trip. Whether you’re in the mood for a quick bite or a sit-down meal, there’s something for everyone. Enjoying a meal here can enhance your overall experience.
Beyond shopping, the Winter Garden Village often hosts community events. Check their calendar to see what exciting activities or seasonal celebrations are coming up. It’s a great way to experience local culture.
Visiting Winter Garden Village is an enjoyable way to spend a day. You can shop, dine, and enjoy the good company of friends or family.
Address: 1000 S. Dillard St, Winter Garden, FL 34787.
11. Have Fun at the West Orange Dog Park
The West Orange Dog Park is a fantastic destination for dog lovers. This spacious park allows your furry friends to run and play freely. It’s the perfect place for pets to socialize and burn off some energy.
The park features separate areas for large and small dogs, ensuring a safe environment for everyone. You can relax while your dogplayfully interacts with others. This is especially enjoyable for pets that love to roam.
Well-maintained grassy areas and shaded spots make it a comfortable space for you too. Bring a chair or blanket, and enjoy some fresh air while watching your dog have fun. This can be a great way to unwind and connect with fellow dog owners.
Regularly, the park hosts events for pets and their owners. Check for activities like dog training sessions or social gatherings. These events encourage community involvement and bring people together.
Visiting the West Orange Dog Park is more than just a walk; it’s about creating memorable experiences with your dog. It’s an ideal outing for pet lovers in Winter Garden.
Address: 200 N. Park Ave, Winter Garden, FL 34787.
12. Dine at the Crooked Can Brewery
The Crooked Can Brewery is a must-try destination for beer lovers. Located in Winter Garden, this popular brewery offers a diverse selection of craft beers. The atmosphere is warm and inviting, making it a great spot to hang out with friends.
Sampling a variety of brews is part of the experience. From IPAs to stouts, you’ll find something to suit every palate. Knowledgeable staff can help guide your choices based on your preferences, ensuring you find a perfect match.
Besides beer, the brewery also serves delicious food. Enjoy a meal while you sip on your favorite drink. The menu features items that complement the beer selection perfectly, making for an enjoyable dining experience.
The brewery regularly hosts events, including trivia nights and live music. These gatherings create a lively and exciting atmosphere, encouraging community engagement. It’s a fun way to spend an evening at Crooked Can.
Visiting Crooked Can Brewery is an experience that embodies the spirit of Winter Garden. Great beer, food, and atmosphere make it an essential stop on your culinary journey.
Address: 426 W. Plant St, Winter Garden, FL 34787.
13. Explore the Oakland Nature Preserve
The Oakland Nature Preserve is a natural wonder just outside Winter Garden. This beautiful preserve offers scenic trails perfect for hiking and birdwatching. It’s a peaceful escape for nature lovers looking to reconnect with the outdoors.
Walking through the preserve, you’ll encounter diverse plants and wildlife. The trails wind through lush landscapes, making it an ideal spot for leisurely strolls or more adventurous hikes. Bring your camera to capture the stunning sights.
Visitors can enjoy guided tours that delve into the preserve’s ecology and history. Knowledgeable guides share fascinating information about the local flora and fauna. It’s an educational experience that elevates your connection to nature.
PIck a picnic spot near the water to enjoy a lovely meal amidst the beautiful scenery. The preserve provides a setting that is both relaxing and invigorating. Enjoy the sounds of nature while you dine.
Exploring the Oakland Nature Preserve offers a great way to appreciate the natural beauty of the area. It’s a wonderful spot for families, couples, or anyone seeking adventure in nature.
Address: 747 Machette Trl, Oakland, FL 34787.
14. Visit the Lake Apopka Wildlife Drive
The Lake Apopka Wildlife Drive is a scenic route that showcases Florida’s natural beauty. Located near Winter Garden, this drive allows visitors to observe wildlife in their natural habitat. It’s a perfect outing for nature enthusiasts and photographers.
The drive meanders through wetlands, offering glimpses of various species. You can spot birds, alligators, and other wildlife, creating an unforgettable experience. Bring binoculars for a closer look at the fascinating creatures.
Along the way, informative signs provide insights into the area’s ecology and history. Learning about the ecosystem enhances your appreciation of the environment. It’s an educational journey suitable for all ages.
Take your time and enjoy the views. There are designated stopping points where you can park and explore. This encourages you to get out and immerse yourself in nature.
Visiting the Lake Apopka Wildlife Drive is a delightful way to connect with the natural beauty of Florida. You’ll leave feeling refreshed and inspired by the wonders of nature.
Address: 2800 Lust Rd, Apopka, FL 32703 (nearby).
15. Take an Outdoors Guided Kayak Tour
Exploring the local waterways through a guided kayak tour is an exciting adventure. These tours provide access to hidden gems in the area while allowing you to experience nature up close. It’s an ideal outing for both beginners and seasoned paddlers.
Trained guides lead the way, ensuring your safety and sharing interesting facts about local wildlife. You’ll learn about the ecosystem while paddling through serene waters. The tours often take you to beautiful spots that are hard to find on your own.
Kayaking offers a unique perspective of the natural beauty of Winter Garden. Gliding through the water is peaceful, and you’re likely to encounter various birds and aquatic life along the way. It’s refreshing to spend time outdoors while being active.
Whether you’re seeking relaxation or adventure, these tours cater to everyone. Many providers offer flexible schedules, allowing you to choose a time that works for you. It’s a great way to enjoy being out on the water.
Taking a kayak tour is a fantastic way to connect with nature and gain a new perspective of Winter Garden’s beautiful surroundings. Each paddle brings new experiences and memories.
Available from multiple local providers.
16. Golf at the Orange County National Golf Center
The Orange County National Golf Center is a premier golfing destination in Winter Garden. This top-notch facility features two championship courses, ideal for golfers of all skill levels. Whether you’re a beginner or an experienced player, you’ll enjoy the stunning landscape and challenging holes.
Each course offers a different experience, providing a variety of challenges that keep the game exciting. Well-maintained greens and scenic views enhance the overall experience. As you play, you’ll be surrounded by beautiful Florida scenery.
The center also offers practice facilities, including driving ranges and putting greens. Perfect your swing or work on your short game before heading out to the course. The on-site pros can provide tips and instruction to improve your skills.
After your game, relax at the clubhouse with a meal or drink. The friendly staff can help you unwind following your round, making it a perfect end to your day on the course.
Golfing at Orange County National Golf Center combines skill, scenery, and relaxation. It’s a memorable experience for anyone who loves the game or wants to learn.
Address: 16301 Phil Ritson Way, Winter Garden, FL 34787.
17. Relax at Lily’s on the Lake
Lily’s on the Lake offers a serene dining experience with beautiful views. Located by Lake Apopka, this restaurant is perfect for lunch or dinner while enjoying waterfront scenery. The relaxed atmosphere makes it a great spot to unwind after a fun day.
The menu features a diverse selection of dishes, prepared with fresh, high-quality ingredients. From seafood to hearty favorites, there’s something for everyone. Pair your meal with a refreshing drink from their extensive beverage menu for a perfect combination.
Outdoor seating allows you to enjoy the gentle breeze and stunning lakeside views. As you dine, you can watch the sun set over the water, creating a picturesque backdrop for your meal. This enhances the dining experience significantly.
The friendly and attentive staff ensure you have a delightful visit. Whether you’re celebrating a special occasion or just treating yourself, Lily’s on the Lake provides excellent service.
If you’re looking for a relaxing dining experience in a beautiful setting, look no further than Lily’s on the Lake. It’s a delightful way to enjoy the beauty of Winter Garden.
Address: 16451 S. Orange Blossom Trl, Winter Garden, FL 34787.
18. Visit Local Craft Fairs and Festivals
Winter Garden hosts exciting craft fairs and festivals throughout the year. These events showcase the creativity and talent of local artisans. You can explore a variety of handmade crafts, food, and entertainment.
Craft fairs often feature unique items like jewelry, home decor, and artwork. It’s a wonderful opportunity to find one-of-a-kind gifts or souvenirs while supporting local artists. Engaging with the makers adds a personal touch to your shopping experience.
Many festivals include live music, games, and delicious food vendors. These events create a lively and energetic atmosphere, perfect for families. Children can enjoy activities designed just for them while parents relax and soak in the fun.
The local community comes together during these events, fostering connections among residents and visitors. It’s a lovely way to experience the culture and spirit of Winter Garden. You’ll leave with memories and perhaps a few unique items.
Attending local craft fairs and festivals is a fun outing filled with creativity, community, and entertainment. Don’t miss the chance to be part of these vibrant events!
Location: Various locations throughout Winter Garden.
19. Attend Holiday Events in Downtown
Winter Garden’s downtown area comes alive with holiday cheer during the festive season. You can participate in a variety of holiday events, including tree lighting ceremonies, parades, and festivals. This creates a delightful atmosphere for residents and visitors alike.
The annual Christmas Tree Lighting is a highlight. The community gathers to celebrate, featuring music, food, and activities for all ages. Watching the tree light up is a magical moment that captures the spirit of the season.
Festive decorations adorn the streets, enhancing the holiday ambiance. Walking through downtown feels enchanting, with twinkling lights and cheerful displays creating a warm invitation to explore. It’s a perfect backdrop for family photos.
Parades and festivals often include local performances, showcasing the talent within the community. Enjoy live music, dance, and arts that reflect the holiday spirit and bring joy to everyone.
Participating in holiday events in Winter Garden helps foster a sense of community. You can create lasting memories with loved ones during this special time of year.
Location: Downtown Winter Garden.
20. Participate in Fitness Events and Classes
Staying active is easy in Winter Garden, where fitness events and classes abound. You can participate in various outdoor activities, from yoga in the park to group runs. These events encourage health and wellness within the community.
Joining a fitness class is a great way to meet new people while improving your health. Many classes cater to skill levels, ensuring everyone is welcome. Whether you’re looking for high-intensity workouts or gentler options, there’s something for you.
You’ll find organized group runs or walks that promote a sense of camaraderie. Enjoy exploring the town while keeping fit. The supportive environment fosters motivation to push your limits together.
Seasonal events, like charity runs or fitness challenges, further engage the community. Participating in these events promotes not just individual health, but collective well-being and unity.
Winter Garden is an active community, and taking part in fitness events is a fun way to stay healthy. Whether you’re a local or just visiting, engaging in these activities will leave you feeling energized and connected.
Location: Various parks and venues throughout Winter Garden.
21. Explore the Historic Winter Garden District
The Historic Winter Garden District is a charming area filled with unique architecture and rich history. Walking through these streets feels like stepping back in time. The well-preserved buildings tell the story of the town’s past.
Join a self-guided tour to take in the sights at your own pace. The district is home to many captivating structures, showcasing different architectural styles. Take your time to admire the details and learn about the stories behind each building.
Informative plaques share interesting facts about the history of the area. You’ll discover how this quaint district has evolved over the years while maintaining its charm. It’s an enriching experience for history buffs and casual visitors alike.
As you explore, you can also visit local shops and cafes. Many take residence in these historic buildings, allowing you to enjoy the best of both worlds. Shopping, dining, and history come together seamlessly here.
Exploring the Historic Winter Garden District paints a vivid picture of the town’s history. It’s an excellent way to appreciate the community’s rich heritage while enjoying local culture.
Location: Historic district of Winter Garden.
22. Ride the Amtrak from Winter Garden Station
The Amtrak station in Winter Garden offers a unique travel experience. You can embark on exciting adventures to various destinations. Riding the train provides a scenic way to explore Florida and beyond.
Traveling by Amtrak is comfortable and convenient. The station’s friendly staff will assist you with any needs as you plan your journey. Many travelers prefer this mode of transportation for its ease compared to driving.
As you travel, enjoy the scenery rolling by. You’ll pass through beautiful landscapes, from lush forests to charming towns. It makes for a leisurely journey where you can sit back and relax.
Taking a train trip can also be a fun outing for families. Kids often find train travel exciting and engaging. It’s an opportunity to create lasting memories while exploring new places together.
Riding the Amtrak from Winter Garden Station opens up a world of travel possibilities. It’s an adventure waiting to happen, right from your community.
Address: Winter Garden Station.
23. Check Out the Local Boutiques
Winter Garden proudly boasts a variety of local boutiques, perfect for unique shopping. These charming shops offer everything from fashion to home goods. Exploring the boutiques is a delightful way to support local artisans and businesses.
The boutiques feature carefully curated selections, ensuring you’ll find something special. Whether it’s a unique piece of jewelry or trendy clothing, the offerings are diverse. You’ll likely discover one-of-a-kind items not found in larger retail stores.
As you browse, take your time to chat with shop owners. Their passion and stories add a personal touch to your shopping experience. They love sharing insights about their products and the inspiration behind their businesses.
Many boutiques host special events and sales, making visits even more exciting. Keep an eye out for seasonal promotions that encourage community engagement and creativity.
Shopping at local boutiques in Winter Garden allows you to find unique treasures while supporting local creativity. It’s a rewarding experience that contributes to the vibrant community.
Location: Various locations throughout Winter Garden.
24. Get Active at the Winter Garden Sports Complex
The Winter Garden Sports Complex is an exciting destination for sports enthusiasts. This facility offers a variety of sports events, leagues, and activities throughout the year. Whether you’re an athlete or a spectator, there’s something for everyone.
Different sports fields cater to various games, including soccer, baseball, and baseball. These well-maintained facilities encourage community involvement and active lifestyles. You can participate in local leagues or simply enjoy watching the games.
The complex often hosts tournaments and events, drawing crowds from the area. Cheer on your favorite teams while enjoying the spirit of competition. It’s a great way to connect with the community.
Families can enjoy quality time together engaging in sports activities. Children can learn teamwork and sportsmanship while having fun. The complex fosters a love for sports in residents of all ages.
Visiting the Winter Garden Sports Complex promotes health, fitness, and community spirit. It’s a dynamic place where sports lovers can thrive and connect with others.
Address: 1350 Plant St, Winter Garden, FL 34787.
25. Visit the Orangewood Community Church
The Orangewood Community Church is a welcoming place for spiritual growth and connection. This beautiful church serves as a hub for community activities and events. You can experience a sense of belonging and fellowship among its members.
The church offers various services, activities, and programs for all ages. Whether you’re seeking worship, education, or community outreach, there’s something for everyone to engage in. The supportive environment fosters connections and spiritual growth.
Participating in church events can enhance your sense of community. From holiday celebrations to volunteer opportunities, there are many ways to get involved. You can meet new friends and support one another in your spiritual journeys.
The serene setting creates an inviting atmosphere for reflection and connection. It’s a place where you can retreat from daily life and focus on personal growth.
Visiting the Orangewood Community Church allows you to embrace the values of community, service, and spirituality. It’s a place where everyone is welcome to grow and connect.
Address: 1120 E. Plant St, Winter Garden, FL 34787.
Final Thoughts
Winter Garden, Florida, is a vibrant destination filled with activities and attractions for all interests. From the rich cultural offerings at the Garden Theatre to the delightful Sundays at the Farmers Market, there’s something for everyone. Nature enthusiasts can explore scenic trails and parks, while sports lovers can join in on local leagues and events.
Culinary experiences abound at breweries and restaurants, showcasing local flavors and craftsmanship. Additionally, the welcoming community spirit shines through at local boutiques, churches, and public events. Each experience adds to the charm and vibrancy of this lovely town.
As you explore Winter Garden, you’ll enjoy a blend of history, nature, and community. For more adventures, don’t miss checking out nearby attractions like the things to do in Eustis. Whether you’re a local or a visitor, the warmth of Winter Garden will leave you with lasting memories and the desire to return.