We talk a lot about Winter Garden, Florida on this blog—and for good reason. Winter Garden is for everyone. It’s close enough to Disney to enjoy the magic but far enough to have its own identity. With a charming small-town feel and a growing, inclusive community, this city is perfect for every stage of life. But today, we’re focusing on the little ones. This guide is all about fun, low- to no-cost activities to enjoy with kids year-round in Winter Garden.
Voted one of the best places to live in Florida, Winter Garden has created a stunning downtown community perfect for a day out with the kids.
A Family-Friendly Destination
Voted one of the best places to live in Florida, Winter Garden has created a vibrant downtown community that’s ideal for a family day out. Thousands of families call it home because it’s a wonderful place to raise kids, make memories, and connect with neighbors.
Start Your Day Off Right – Morning Adventures
Ride the West Orange Trail
Beat the heat with an early ride or walk on the 22.26-mile paved West Orange Trail, which starts in Winter Garden and stretches all the way to downtown Apopka. Whether you’re strolling, skating, or biking, it’s a scenic way to experience Central Florida’s natural beauty. Bike rentals are available at each trailhead.
(Fun fact: The West Orange Trail is part of the future 250-mile Coast to Coast Connector Trail linking Florida’s Atlantic and Gulf coasts.)
Bike Rental Options:
- Orlando Bike Rental
- Wheel Works
If you make it to the Apopka Station trail end, reward yourself and the kids with a break at the playground and shaded picnic area.
Location: 111 S Forest Avenue, Apopka, FL 32703
Beat the Afternoon Heat
Central Florida Train and Heritage Museum
Train lovers, rejoice! This museum showcases Winter Garden’s rich railroad history. Kids and adults alike will be fascinated by the exhibits.
Hours: 1 pm to 5 pm daily
Location: 101 S Boyd Street, Winter Garden, FL 34787
The Garden Theatre
Wander down Plant Street and you’ll find The Garden Theatre, a retro gem hosting everything from kid-friendly movies to theatrical performances. It’s a cultural must-see that adds a little drama (the good kind) to your afternoon.
Box Office Hours: Tuesday–Friday, 12 pm to 4 pm
Location: 160 W Plant Street, Winter Garden, FL 34787
Capture the Moment – Selfie Stops
Don’t forget to take pictures! Winter Garden is packed with murals and Insta-worthy spots made for capturing sweet moments with the kids.
Top Selfie Spots:
- City Hall: 300 West Plant Street
- Orange Mural: 100 W. Plant Street
- Shoo Shoo Baby Mural: 117 S Boyd Street
- Plantation Jewelers: 115 W Plant Street
- Polkadotz: 12 W Plant Street
- Livetrends Boutique (indoors): 279 Tremaine Street
Cool Down with Ice Cream
Winter Garden knows how to keep kids (and parents) happy with several sweet spots downtown.
Favorites Include:
- Scoops Old Fashioned Ice Cream (99 W Plant Street)
- Kelly’s Homemade Ice Cream
- Harrell’s Hot Dogs & Ice Cream
Relax with a Picnic
Newton Park
Located on Lake Apopka, Newton Park offers a peaceful setting with a playground, shaded picnic spots, and open grassy fields. It’s a family favorite for a reason.
Address: 31 W Garden Avenue, Winter Garden, FL 34787
Splash & Play
Downtown Winter Garden Splash Pad
Let the kids run wild and stay cool at this vibrant splash pad in the heart of town.
Hours: 9 am to 9 pm
Location: 104 S Lakeview Ave, Winter Garden, FL 34787
Winter Garden Playground
Wrap up your adventure at the city’s largest playground, perfect for letting out that last bit of energy before bedtime.
Hours: 8 am to 8 pm
Location: 501 Crown Point Cross Road, Winter Garden, FL 34787
Pro tip: End your day here—your kids may just nap the whole way home.
Venturing a Bit Further?
- Winter Park: Rent a crystal kayak and cruise through its scenic canals.
Get Up and Go Kayaking – Winter Park - Clermont: Visit the Citrus Tower and Citrus Museum.
More on Clermont’s Citrus Tower - Rock Springs Run: Perfect for nature-loving families ready for a mini adventure.
Winter Garden makes planning an entire day with the kids easy. With safe, fun, and memorable activities that spark creativity, learning, and joy, there’s something here for every family. And as the city continues to grow, so do the experiences for locals and visitors alike.
Thinking about putting down roots nearby? A trusted real estate agent can help you find the perfect home just a short drive from all these amazing Winter Garden attractions.
Once the kids are tucked in, treat yourself to a date night in nearby Winter Park. And if you’re planning your next move or simply curious about life in Central Florida, the Erica Diaz Team is your go-to expert 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 Clermont and Winter Garden.
