Christie Cronan

Winter Park is one of my family’s favorite cities. It’s full of history, charm and travel gems, and offers families some of the best attractions, activities and memories in the Central Florida area.

Farmer's Market

A Saturday morning just isn't the same without a family stroll at the local Winter Park Farmers Market. Held at the historic train depot, this famous corner of the city features some of the best local produce, fresh flowers and plants, as well as baked goods from the area.

Just walking among all the morning hustle and bustle brings out an explorer’s spirit in my kids. Picking their own veggies for dinner, sampling the fresh-popped kettle corn, smelling the fresh baked bread, pointing out their favorite homemade pastries -- it's a MUST experience for families.

Held every Saturday from 7 a.m. - 1 p.m. (except the third Saturday in March) -- it's worth the early wake-up.

Park Avenue

Just a short walk from the Farmers' Market is our family's next favorite spot for a stroll. Winter Park's Park Avenue and surrounding side streets feature cobblestone roads, a beautiful rose garden, and picturesque old town traditions.

Train station

If your kids love trains as much as mine do, you'll have to make a quick stop at the Winter Park Train Station. A real working train station, you can watch the trains pull right up to the beautiful little depot.

Central Park

With 11 acres of green lawns, fountains, and oak trees, this is the most well-known park in the city. It hosts many famous annual events, including art festivals, holiday celebrations and concerts, but is also perfect for your own small picnics and an afternoon of Frisbee toss, and has many a time saved my family's sanity. Sometimes your kids just need to "run" it out. Don't miss the rose garden at the south end of the park.


Need a non-chain restaurant where your family can grab a bite? There's plenty of amazing sidewalk eateries right on Park Avenue. Enjoy great people- and dog-watching right from your cafe table and enjoy cuisine ranging from romantic Italian to classic American. Our kids loved getting ice cream on a hot Florida day from Kilwins.


Let's not forget mommy's favorite pastime, shopping. Of course in between all of those delicious eating hot spots are upscale stores, perfect for a little window-shopping.

 The Winter Park Scenic Boat Tour promises a beautiful look at Florida wildlife, landscapes, gorgeous mansions and lots of fun

- Christie Cronan for VISIT FLORIDA


Famous Scenic Boat Tour

Our next stop on our Saturday afternoon was a family first. The Famous Winter Park Scenic Boat Tour is a one-hour tour of the lakes of Winter Park. This tour, in operation since 1938, promises a beautiful look at Florida wildlife, landscapes, gorgeous mansions and lots of fun facts from the tour guide.

Shady Playgrounds

Being one of the oldest cities in the Central Florida area means boasting some of the oldest trees in the area, too; some are more than 400 years old. That means your kids will love playing in one of the many shady oak tree playgrounds across the area. Lovingly known as the "castle park," the Community Playground offers swings, slides, and a beautiful wooden-structured playground with all the nooks, crannies and climbing your kids can handle.

Mead Botanical Garden

Haven't got enough of the outdoors yet? Just a short car ride away is Mead Botanical Garden, a perfect place for the family to begin winding down for the day. Your family can enjoy Winter Park's natural beauty, all canopied by the wonderful oak trees. A perfect place for a family gathering, you can explore some of the many botanical gardens or just enjoy an afternoon picnic, all for free.

Rollins College

No visit to Winter Park is complete without a visit to Rollins College. Voted the #1 most beautiful college campus by Princeton Review (See? I did pay attention during our boat tour!), this famous liberal arts college offers some of the most beautiful architecture, lake views and landscaping of Winter Park. You might be able to persuade your kids to go to college after all. (Wink-wink.)

Winter Park Village

After a long day, it was nice to end with food, entertainment and sights all wrapped up into one. Winter Park Village offers families much of the outdoor mall atmosphere with lots of notable chain restaurants, shopping and a movie theater. And while our family certainly enjoyed much of the deliciousness and atmosphere, that's not the main reason that we show up.

Nestled across the street from the movie theater is a gigantic checkers board and chessboard. With pieces as large as my toddler, my kids loved engaging in a good old-fashioned game -- no technology required.

We hit seven of our favorite Winter Park family activities spots in one day. We got to explore, discover, learn, and play without ever being bored.

If you’re going to nearby Orlando, be sure to check out 5 Great Family Dinner Shows in Orlando and 25 Orlando Attractions for Kids That Are NOT a Theme Park.