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Family-Friendly Activities in Winter Park, FL for Every Season

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Winter Park is a charming community known for its family-friendly atmosphere and year-round activities that cater to all ages. Whether you’re enjoying the beautiful Florida weather in the spring or cozying up in the winter, there’s always something fun to do with the family. Here are some activities and events to enjoy in Winter Park throughout the year:

Fall: Enjoy Family Fun at the Autumn Art Festival
Scenes from the 50th Annual Winter Park Autumn Art Festival · the32789

The Winter Park Autumn Art Festival is a wonderful way to celebrate the fall season with family. Held in October, this festival features local artists, live entertainment, and fun activities for children. Enjoy delicious food, participate in crafts, and take in the beautiful fall colors in the park.

Winter: Experience the Magical Nights of Lights
Winter Park home featured in ABC's Great Christmas Light Fight

During the winter months, Winter Park lights up for the holiday season with the Nights of Lights celebration. Take a family stroll along Park Avenue and admire the dazzling holiday displays. Don’t forget to stop by the Winter Park Library for special holiday events and storytimes, making it a magical experience for young children.

Spring: Explore the Park Avenue Sidewalk Art Festival
62nd Annual Winter Park Sidewalk Art Festival Named 'Complete Success' · the32789

Every spring, the Winter Park Sidewalk Art Festival transforms Park Avenue into a vibrant outdoor gallery. This three-day event showcases works from talented artists while offering live music, food vendors, and plenty of activities for kids. It’s a great opportunity for families to explore local art and enjoy the warm weather.

Summer: Take Advantage of the Farmers’ Market
Winter Park Farmers Market

The Winter Park Farmers’ Market is held every Saturday morning, making it a perfect summer outing for families. Stroll through the market, where you can find fresh produce, baked goods, and unique crafts from local vendors. Kids will love sampling fruits and treats while learning about healthy eating and supporting local businesses.

Year-Round: Visit Central Park
Winter Park Parks & Recreation Department (@ParksandRecWP) / X

No matter the season, Central Park in Winter Park is a great spot for family outings. With playgrounds, picnic areas, and beautiful walking paths, it’s perfect for a day of fun in the sun. Families can also rent swan boats at Lake Osceola for a unique and enjoyable experience on the water.

Thinking of Moving to Winter Park?

If you’re excited about the idea of living in a community that offers endless family-friendly activities, reach out to Wemert Group Realty at (321) 567-1202 to start finding your ideal family-friendly home in Winter Park today!