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Winter Park Is Perfect for Families — Here’s Why

Niche, a website that ranks colleges, schools, cities, neighborhoods, and even companies, identifies Winter Park, Florida as one of the best suburbs in the Orlando area. With a population of nearly 31,000, Winter Park is known for its highly-rated public schools, its close proximity to both downtown Orlando and the beach, and its outdoor activities, not to mention its history and charm.

Family Fun in Winter Park

When it comes to family fun in the popular suburb, the options are endless. For eight ideas, consider our list below.

Winter Park Farmers Market

Each Saturday morning, the historic train depot transforms into an impressive farmers market. Shoppers can fill their bags with local produce, baked goods, fresh flowers, and homemade gifts, like soaps and candles. Make it a family affair and bring your four-legged friend too!

Central Park

This 11-acre green space, complete with lawns, fountains, and oak trees, was originally at the center of the town. Depending on the time of year, it serves as the backdrop for the city’s art festivals, holiday events, and concerts. It’s also the perfect spot for an afternoon picnic (with goodies from the farmer’s market, of course) and a game of frisbee or catch. Head to the rose garden for an added adventure.

Park Avenue

Central Park’s main street, appropriately named Park Avenue, is lined with over 140 restaurants, shops, and museums. Many of the dining options offer outdoor seating, so your pup is welcome too. After you fuel up, get a jump start on your holiday shopping as you wander in and out of stores like Rifle Paper Co. and Peterbrooke Chocolatier. Don’t worry — your dog can venture into many of the shops as well!

Winter Park Train Station

This beautiful little spot is a must-do for tiny fans of Thomas the Tank Engine and Friends. The whole family will enjoy watching the trains come and go.

Winter Park Scenic Boat Tour

This one-hour tour of the lakes of Winter Park includes Florida wildlife sightings, landscapes, and beautiful homes. You’ll see sights like Rollins College, Albin Polasek Museum & Sculpture Gardens, Kraft Azalea Gardens, and more. Even better, you’ll get a brief history of the local area as well.

Local Playgrounds

Do your kids and fur babies have some extra energy to burn? Take your family to a nearby playground! The Community Playground, also called Castle Park, is a local favorite. Sit back and relax while your kids swing, slide, and climb all afternoon.

Winter Park Village

This outdoor shopping center has something for everyone, including a gigantic checkers board and chess board located across from the movie theater. With pieces the size of a toddler (!), it offers the perfect entertainment for kids (and adults) of all ages.

Popcorn Flicks in the Park

Popcorn Flicks, a collaboration between the city of Winter Park and the Enzian Theatre, is held on the second Thursday of each month and features classic films, like The Addams Family (October 13, 2022) and One Hundred and One Dalmatians (November 10, 2022). Be sure to bring a blanket and snacks and grab your spot between 7 and 8 p.m. The movie starts at sunset for an optimal viewing experience.

Note that parts of Winter Park suffered from flooding during Hurricane Ian. The city has committed to a clean-up plan, which is already in progress.

Let The Urban Dog Group help you with your real estate needs. Contact Christine Elias at


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