Looking for fun, affordable things to do with kids in Winter Garden, Florida? This family friendly guide covers low to no cost activities you can enjoy year round, from outdoor adventures to downtown favorites that make planning a full day easy.
We talk a lot about Winter Garden on this blog, and for good reason. It offers the right balance of small town charm and steady growth. Close enough to Disney for the magic, yet grounded in its own strong sense of community, Winter Garden is a place where families truly thrive. Today, the focus is on activities designed for kids.
A Family Friendly Destination
Consistently voted one of the best places to live in Florida, Winter Garden has built a vibrant downtown designed with families in mind. Walkable streets, public gathering spaces, and community events make it a city where kids can explore and parents can relax. Many families choose to call it home because it is a place to grow, connect, and create lasting memories.
Start Your Day Right: Morning Adventures
Ride the West Orange Trail
Beat the heat with an early walk, ride, or skate along the 22.26 mile West Orange Trail. The trail begins in Winter Garden and stretches to downtown Apopka, offering shaded paths and scenic views that highlight Central Florida’s natural beauty. Bike rentals are available at trailheads, making it easy even if you do not have your own gear.
Fun fact. The West Orange Trail is part of the future 250 mile Coast to Coast Connector Trail that will link Florida’s Atlantic and Gulf coasts.
Bike rental options include:
- Orlando Bike Rental
- Wheel Works
If you make it all the way to the Apopka Station, reward the kids with time at the playground and a shaded picnic break.
Location: 111 S Forest Avenue, Apopka, FL 32703
Beat the Afternoon Heat
Central Florida Railroad Museum
Perfect for curious kids, this museum highlights Winter Garden’s railroad history through hands on exhibits and restored rail cars. It is a simple, educational stop that both kids and adults enjoy.
Hours: 1 pm to 5 pm daily
Location: 101 S Boyd Street, Winter Garden, FL 34787
The Garden Theatre
A stroll down Plant Street brings you to this restored historic theater. From family friendly movies to live performances, it adds a creative touch to any afternoon downtown.
Box Office Hours: Tuesday through Friday, 12 pm to 4 pm
Location: 160 W Plant Street, Winter Garden, FL 34787
Capture the Moment: Photo Stops
Winter Garden is full of colorful murals and fun backdrops that make perfect photo opportunities with the kids.
Favorite selfie spots include
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Winter Garden City Hall, 300 W Plant Street
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Orange Mural, 100 W Plant Street
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Shoo Shoo Baby Mural, 117 S Boyd Street
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Plantation Jewelers, 115 W Plant Street
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Polkadotz, 12 W Plant Street
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Livetrends Boutique, 279 Tremaine Street
Cool Down with Ice Cream
No family day is complete without a sweet treat. Downtown Winter Garden has several ice cream spots that are always a hit with kids and parents.
Local favorites
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Scoops Old Fashioned Ice Cream, 99 W Plant Street
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Kelly’s Homemade Ice Cream
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Harrell’s Hot Dogs and Ice Cream
Relax with a Picnic
Newton Park
Set along Lake Apopka, Newton Park offers a calm place to slow down. Families love the playground, shaded picnic tables, and open green space that gives kids room to play.
Splash and Play
Downtown Winter Garden Splash Pad
Let the kids cool off at this popular splash pad located in the heart of downtown.
Hours: 9 am to 9 pm
Location: 104 S Lakeview Avenue, Winter Garden, FL 34787
Winter Garden Playground
End the day at the city’s largest playground. It is the perfect place for kids to burn off any remaining energy.
Hours: 8 am to 8 pm
Location: 501 Crown Point Cross Road, Winter Garden, FL 34787
Pro tip. Save this stop for last. There is a good chance your kids will nap on the ride home.
Venturing a Little Further?
If you are open to a short drive, there are more family friendly options nearby.
Winter Park offers scenic canals and clear kayaking experiences.
Clermont is home to the Citrus Tower and Citrus Museum.
Rock Springs Run is ideal for families who enjoy outdoor adventures.
Families who love the pace of Winter Garden often explore nearby communities as well. Mount Dora is a popular option for those who want a walkable downtown, local festivals, and a strong sense of community. If you are curious about homes in that area, working with a trusted mount dora real estate agent can help you understand neighborhoods, pricing, and lifestyle fit.
Winter Garden makes it easy to plan a full day with kids. Safe spaces, engaging activities, and a welcoming community create experiences that encourage learning and fun. As the city continues to grow, so do the opportunities for families who live here and those who visit.
If you are thinking about putting down roots nearby, working with a trusted real estate agent can help you find the right home close to everything Winter Garden has to offer. For buyers comparing Winter Garden with nearby cities, a knowledgeable mount dora realtor can also help you weigh your options and explore homes throughout Central Florida.
Once the kids are tucked in, enjoy a date night in nearby Winter Park. And if you are exploring a move or simply curious about life in Central Florida, the Erica Diaz Team is your go to resource for real estate in Winter Garden and beyond.
Contact the Erica Diaz Team today and discover why so many families are choosing to grow in Winter Garden and Clermont.
