Historic Downtown Winter Garden is both charming, and surprisingly kid friendly. It's the perfect Central Florida destination for a day trip or weekend getaway.

Winter Garden Florida seemed like just another town on our map.

Until recently, that is. In the three years since we transplanted to Central Florida we’ve done a lot of exploring. But it wasn’t until I had three friends (in so many weeks) RAVE to me about this “charming” little town they had discovered, that I decided to check out Historic Downtown Winter Garden.

But was it kid friendly?

I wasn’t sure. None of the people who recommended Winter Garden’s Historic Downtown to me had young kids, so I did a little research to make sure it wasn’t too fancy for our active girls. While there are some nice restaurants and shops, overall it seemed pretty relaxed and low key.

There’s also a popular Farmer’s Market every Saturday – and that (along with the enthusiastic recommendations of my friends) was enough to make us grab our day pack, load up the family, and head out for a day in Historic Downtown Winter Garden.

RELATED: How to Prep for Family Outings So That They Are Easy to Do + Actually Fun

We discovered so many kid friendly things to do on our spontaneous getaway to Winter Garden Florida.

The Winter Garden Farmer’s Market is Awesome.

Located in the Downtown Pavilion, the market is spacious and welcoming. As you can see, it’s also kid and pet friendly.  There’s wide paths between stalls, easy stroller access, and lots of places to rest in the shade. I was honestly surprised at how many families with young kids were there, until I discovered,

There’s also a FREE Splash Pad right next to the Market.

We discovered so many kid friendly things to do on our spontaneous getaway to Winter Garden Florida.

Our girls were totally thrilled about that! The splash area was a total surprise to us, so we hadn’t packed bathing suits. We did let them play for a bit – there was plenty of time to dry off in the sun while we wandered the market. Next time we’ll pack a lunch, and plan on some real soaking wet fun!

There are a ton of vendors with everything from fresh fruit and flowers, to gourmet treats and jewelry. Towards the back end of the farmer’s market, there’s a covered patio with a huge selection of fresh fruits and veggies — right next to this is the public bathrooms. (Always handy to know!) There was also some comfortable seating in the shade, right in the center of the market.

We discovered so many kid friendly things to do on our spontaneous getaway to Winter Garden Florida.

After the Farmer’s Market, we headed to Harry & Larry’s BBQ for lunch.

But we totally had to stop and check out this kid-friendly train display in a storefront on our way there.

We discovered so many kid friendly things to do on our spontaneous getaway to Winter Garden Florida.

As you can see, it was a hit for several of the kids passing by. There’s actually little buttons where the kids can turn the trains on themselves — and we stayed there for quite awhile just to watch the fun!

Harry & Larry’s BBQ is a true, hole-in-the-wall restaurant. We walked past the entrance twice, trying to find our way in! The relaxed atmosphere and kid friendly food options made it the perfect place for us to relax for a bit. It did take awhile for the food to get to our table, but it was worth the wait. We loved checking out the fun vintage style decor while we waited.

We discovered so many kid friendly things to do on our spontaneous getaway to Winter Garden Florida.

When our meal came, we dug in before I remembered to take pictures! The food was yummy though – you’ll just have to try it out for yourself.

The Centennial Plaza Fountain was actually our favorite part of Winter Garden’s Historic Downtown.

It’s circled by benches and swings, and is nicely shaded. Such a pretty spot! We actually spent quite a while there. The girls were happy to play around the fountain, and we were happy to sit and chat. When I looked over our pictures from the day, I could see the relaxation in our faces:

We discovered so many kid friendly things to do on our spontaneous getaway to Winter Garden Florida.

It’s hard not to be relaxed though, when you’re surrounded by this:

We discovered so many kid friendly things to do on our spontaneous getaway to Winter Garden Florida.

While we were hanging out by the fountain, we saw people walking by with these huge, delicious looking ice cream cones. When we were planning our day, the girls decided that finding an awesome ice cream shop was the one thing they really wanted to do on this particular day trip.

Scoops Old Fashioned Ice Cream Shop totally fit the bill.

We discovered so many kid friendly things to do on our spontaneous getaway to Winter Garden Florida.

There were so many flavors of ice cream to choose from – and the cones were HUGE. Definitely more than we could eat! On our way into the store, I could hear people outside raving about how good the ice cream was. And it was totally delicious. And check out the old fashioned charm!

Scoops is located on the ground floor of the historic Edgewater Hotel, which now functions as a bed and breakfast. We accidentally exited out the back door of the ice cream shop and found ourselves in the old hotel lobby – it felt like we were transported back in time! I  had to snap a few photos:

We discovered so many kid friendly things to do on our spontaneous getaway to Winter Garden Florida.

We discovered so many kid friendly things to do on our spontaneous getaway to Winter Garden Florida.

Historic Winter Garden Florida turned out to be a surprisingly relaxing and  kid friendly destination for us.

We could have spent another hour at least at the splash pad, and barely scratched the surface of the Farmers Market. The Heritage Museum and the Central Florida Railroad Museum are both places we would have liked to explore, but our kiddos totally ran out of steam. We’ll have to hit them next time, I guess!

All in all, it was an awesome way to spend a Saturday in another one of our everyday adventures!

We discovered so many kid friendly things to do on our spontaneous getaway to Winter Garden Florida.

 

Things to Do in Historic Downtown Winter Garden: Kid Friendly Fun
Jamie Siebens

Jamie writes about living intentionally and finding beauty and perspective in the adventures of everyday life. When she’s not writing, she’s living her own adventures – working full time at an ER registration desk, parenting two spicy girls, and collaborating with her husband on the remodel of a former one-room schoolhouse on their homestead in rural Wisconsin.

One thought on “Things to Do in Historic Downtown Winter Garden: Kid Friendly Fun

  • Another hidden gem in downtown is Mimi’s Community Theater located at the Winter Garden Masonic Lodge 230 West Bay Street. Pretty much right across the street from city hall and a Crooked Can.
    Mimi’s has been in town for two years now. We are a no experience, everyone welcome group.
    Our motto is “Local talent all the time”. Check us out on Facebook we have a murder mystery dinner show coming up soon.
    October 6 and 7 at Showcase 12100 West Colonial Drive. Winter Garden.
    October 20 at Bahia Shriners in Apopka.
    Tickets are on sale now on our Facebook page under our events.
    Come check us out…you will be glad you did.

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