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If you love picking fresh produce and checking out local crafters and fresh food, you will love the Winter Garden Farmers Market.   They have a large variety of vendors and have grown quite a bit in a few short years to be one of the best Farmers Markets around town.  The kids will love dancing to live music and trying yummy food samples.

Hours: Saturdays 9 am to 2 pm
Location: 104 S Lakeview Ave, Winter Garden, FL 34787

Garden Theatre

The Garden Theatre plays host to many plays and movies year-round. They offer interactive sing along movies sure to please you and your kids.  During the summer, the Garden Theatre offers summer movies featuring children’s favorites at discounted rates that you will not want to miss. 

Hours: Box office opened Tuesday through Friday from 12 pm to 4 pm, Showtimes vary
Location: 160 W Plant Street, Winter Garden, FL 34787

Scoops Old Fashioned Ice cream

If you are looking to treat your child to something sweet, check out Scoops Old Fashioned Ice Cream Parlor.  It is a Winter Garden staple.  Take a step back in time and enjoy hot dogs and ice cream in a vintage setting. 

Hours: Tuesday through Saturday 12 pm to 8 pm, Sunday 1 pm to 8 pm, Closed Mondays.
Location: 99 W Plant Street, Winter Garden, FL 34787

Central Florida Train and Heritage Museum

If your child loves trains, be sure to visit the Central Florida Train and Heritage Museum.  Climb aboard an old train to explore.  Then head inside to see how the railway system has helped in the development of the state of Florida in the museum along with the history of the town of Winter Garden and its heritage.

Hours: 1 pm to 5 pm daily
Location: 101 S Boyd Street, Winter Garden, FL 34787

West Orange Trail

If you and your family like to be active, then you must check out the West Orange Trail.  It is a 22-mile-long paved trail where you can run, walk or bike.  Pack your bikes or wagon, or explore by foot.  The trail takes you from Oakland, through Winter Garden to Apopka.  If 22 miles seems a bit long, you can pick up the trail at 4 different stations and turn around when you are ready to be done.  If you start at Winter Garden Station, head to Chapin Station, and since both have playgrounds the kids will be sure to enjoy the outing. 

Hours: Sunrise to Sunset
Location: 455 E Plant Street, Winter Garden, FL 34787

Winter Garden Playground

There are many playgrounds throughout the city of Winter Garden.  I could probably write an article on playgrounds alone, but that is for another time.  One of my favorites, or should I say my daughter’s favorite is Chapin Station.  This is one of the bigger playgrounds around town so there is much for your child to see and play on.  Pack a lunch and make an afternoon out of it.

Hours: Daily from 8 am to 8 pm
Location: 501 Crown Point Cross Rd, Winter Garden, FL 3478

Winter Garden Bowl

If you or your kids love to bowl, as my little one does, visit Winter Garden Bowl.  Don’t let the outside fool you.  Though the outside may be a little plain and not the most welcoming, inside it is clean and reasonably priced.  They are kid friendly and are a part of the free summer bowl program, which is offered nationwide.  Great activity on a rainy day!

Hours: Vary by day
Location: 715 S Dillard Street, Winter Garden, FL 34787

Cruz N Car Show

A fun family event that is held quarterly in the downtown area of Winter Garden worth mentioning, is the Cruz N Car Show.  Here you will find cars that range from old classics of the 30s, 40s, and 50s to newer muscle cars of today, and everything in between.  These cars are in show quality pristine condition.  It’s a great activity for family young and old.  My daughter loves finding different color cars, especially the pink ones, and dancing to the retro music!

Hours: 4 pm to 8 pm. 
Held January 18, April 18, June 20, and September 19, 2020
Location: W Plant Street, Winter Garden, FL 34787

What is your favorite thing to do in Winter Garden with kids?

Written by Megan Daniels