Top 10 Ways to Explore Winter Garden

Now is an ideal time to discover – or rediscover – the charm of Winter Garden. From iconic landmarks, recreational venues, to unique shops and restaurants and so much more, there is always something new to experience. Whether you are a resident or visitor, make sure you check off your list the following Top 10 Ways to Explore Winter Garden:

1. Dine al fresco.

Enjoy the fresh air and the charm by dining outdoors along the brick-lined streets of historic downtown. Expanded patio areas dotted with umbrella tables are located throughout. Nothing beats a dinner under the stars and twinkling lights! Check out all the yummy restaurants in Downtown Winter Garden here!

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2. Discover a new favorite place to shop.

Venture into a store for the first time and you just may discover a new favorite place to shop. Find keepsakes and locally made products at downtown boutiques. It is a great time to support local merchants while seeking hidden gems! Check out more Downtown Winter Garden shopping here!

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3. Reacquaint with friends at a new-to-you bistro.

Whether it is for brunch, happy hour, or dinner, venture to that place you have always been meaning to try. An abundance of trendy bistros and cafes – and the City’s own brewery — makes the perfect meeting spot to reacquaint with friends. Find your perfect bistro here!

4. Grab a to-go meal for a picnic outdoors.

Grab a swing downtown or head to one of the City’s nature parks to create a romantic picnic for two or an outdoor family adventure. With convenient take-out options, the only thing you will have to bring is your appetite! Learn more about WG Curbside here!


5. Visit a cultural venue. 

Whether you have never been or returning to see what’s new, local cultural venues are fun – and free– for the whole family. Learn about the City’s juicy past by visiting the Winter Garden Historical Museum or taking their guided small group walking/biking tour. The sprawling model train display at the Central Florida Railroad Museum has all the bells and whistles to delight all ages. The SOBO Art Gallery displays monthly exhibitions worthy of worldwide attention. Purchase tickets for top-notch live plays, concerts, and movies at the historic Garden Theatre. More info on cultural venues here!

6. Relax in an “outdoor” living room.

No invitation needed to grab a seat — on a swing or bench — beneath colorful flowers and lush greenery while becoming entranced by the mesmerizing renaissance-inspired mosaic-tiled fountain. Unwind enveloped in historic charm at Centennial Plaza –the local hub and heartbeat of the city. Pets welcome in this living room! It is also the best seat in the house to enjoy weekly live music at Friday’s on the Plaza, 7-9 pm. Find out what’s happening here!

7. Hit the trail.

The 22-mile award-winning West Orange Trail runs right through the center of downtown, which makes a perfect resting stop. Hop on a bike (rentals available at downtown trailhead), or go for a stroll to explore the trail’s scenic surroundings. More info on the West Orange Trail here!

8. Visit your hometown national award-winning Farmers Market.

From fresh local produce and pre-packaged foods to fresh plants and flowers, a visit to the outdoor weekly Winter Garden Farmers Market (Wednesdays 3-7 pm and Saturdays 9 am–2 pm) is not always convenient, but also fun (pets welcome too!). Repeatedly ranked best in the nation and state by American Farmland Trust, how fortunate to have this renowned Farmers Market in your own backyard! Find out more about the Winter Garden Farmers Market here!

9. Escape to Old Florida.

From breathtaking sunsets over Lake Apopka at scenic Newton Park, to sprawling acres of Florida vegetation at Tucker Ranch Recreational Park and Nature Preserve, the authentic scenery at City of Winter Garden’s nature parks allow a retreat to Old Florida along with entertaining recreational amenities. Explore nature parks here!

10. Snap away to share with friends and family.

Downtown’s historic charm is the perfect backdrop for taking photos and selfies. Show your friends and family why Winter Garden is one of the most photographed downtowns in Central Florida, according to the Orlando Film Commission. Be sure to capture all the landmarks: Clock Tower, Centennial Plaza Fountain and Gazebo, Train Caboose, City Hall, Water Tower….and so many more unique and enchanting backgrounds.

Whether your exploration uncovers new discoveries or provides some nearby convenient fun, locals are the key to revitalizing the community and small businesses appreciate the support. Not to mention, all the fun memories that will be made taking on the Top 10 challenge!


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