For more fun things to do around Orlando with kids, check out our list of 100 FREE Things to Do with Kids in Orlando, 20 Kid-Friendly Hikes in Central Florida, and 25 Secret Orlando Spots Kids Will Love.

Fun Things to Do with Kids in Winter Park, Florida

1. Central Park

Located in the heart of Winter Park, Central Park is a large green space perfect for picnics, playtime, and family strolls. Kids can run and play while parents enjoy the scenic beauty, fountains, and walking paths. There’s also a Rose Garden on the south side of the park.

2. Community Center Pool

This family-friendly pool offers a shallow splash play area for little ones, a large swimming area, and shaded spots for parents to relax. It’s a great place to cool off during the hot Florida months.

3. Community Playground

Known as "Castle Park," this wooden play structure boasts climbing elements, swings, and slides for endless fun. The park also features a rentable pavilion for parties, nearby restrooms, a scenic walking/jogging trail, and a small lake perfect for fishing.

4. Kraft Azalea Garden

Tucked along the lakefront, this hidden gem is often called Winter Park’s secret garden. Explore the five-acre park, shaded by cypress trees and filled with Old Florida beauty. It’s also a great spot for capturing memorable photos!

Spend an idyllic afternoon wandering Mead Botanical Garden. Photo by the author

5. Mead Botanical Garden

For a mix of education and fun, visit Mead Botanical Garden. Kids can explore nature trails, spot wildlife, and enjoy the butterfly garden. There’s even a fun little creek for splashing around on hot days. Plus, it’s completely FREE to visit!

6. Monkey Joe’s Winter Park

Monkey Joe's is an indoor play park filled with fun inflatables, a jungle gym, toddler play area, and arcade. The inflatable playground is designed for ages 12 and younger, with a special mini monkey area for ages 3 and under.

7. Morse Museum

Introduce kids to the beauty of art, especially the colorful stained glass works of Louis Comfort Tiffany, at Morse Museum. During the summer, the museum offers Friday Family Films and Tuesday Family Tours.

8. Phelps Park

Rebuilt in 2021 with the help of resident input, Phelps Park is a favorite among locals! This park features a fun playground with climbing structures, slides, and swings, as well as shaded picnic pavilions and nearby restrooms.

9. Rollins Museum of Art

The Rollins Museum of Art offers a fun and educational experience, with a collection of paintings, sculptures, and interactive exhibits. Plus, admission is FREE for visitors of all ages. Families can explore artwork from around the world in a relaxed setting. Rollins even offers a free Family Studio program each month with interactive experiences inspired by current exhibits.

10. Winter Park Library

The Winter Park Library is a favorite local library for little ones, and for good reason! The children’s area features cozy reading nooks, several story time programs, toys, puzzles, and computers. It’s the perfect place to spark little imaginations and make learning an adventure.

11. Winter Park Scenic Boat Tour

Explore the area's beautiful lakes and canals on the Winter Park Scenic Boat Tour. Along the guided tour, families can enjoy spotting wildlife, historic homes, and lush scenery while cruising through the tranquil waters of Winter Park.

12. Winter Park Train Station

Arrive in fashion with a trip on the SunRail! Riding the SunRail to Winter Park is an exciting and stress-free way to explore the town while enjoying the sights along the way. Kids will love arriving right in the heart of Winter Park, just steps away from parks, shops, and restaurants.

Stroll the gorgeous Park Avenue Shopping District for shopping, gifts, and lunch. Photo courtesy Visit Orlando

Winter Park Shopping & Restaurants

13. 4 Rivers Smokehouse

This popular smokehouse has several locations throughout Florida, but it got its start in Winter Park, so it’s a fitting stop when visiting!

14. Park Avenue Shopping District

Since 1887, Park Avenue has been a go-to destination for great food and unique shopping. Stroll the tree-lined streets, explore hidden gardens, and enjoy cozy cafés and stylish boutiques. Often called “Little Europe,” it’s the perfect mix of elegance and small-town charm.

15. Briarpatch Restaurant

A must-visit on Park Avenue for breakfast or brunch, Briarpatch offers delicious pancakes, waffles, and kid-friendly options in a cozy setting.

Bring kids to Krispy Kreme and watch the fresh doughnuts roll down the conveyor belt. Photo by the author

16. Krispy Kreme Doughnuts

Our family trips to Winter Park are not complete without a stop at Krispy Kreme—especially when the "Hot Now" light is glowing! Watch the doughnuts get a glaze bath aboard the conveyor belt, with a front-row seat. Plus, don’t forget to grab a classic paper hat for your little one.

17. Winter Park Village

Winter Park Village is a great spot to visit with kids, offering a mix of shops, restaurants, and entertainment. With a movie theater, outdoor seating areas and lawn games, it’s the perfect spot for a day of shopping and play with kids.

18. Toasted

This casual eatery specializes in gourmet grilled cheese sandwiches and burgers, making it a hit with “little muensters” and parents alike.

Stay at the family-friendly Alfond Inn for relaxing vacations in Winter Park. Photo courtesy Visit Orlando

Kid-Friendly Hotels in Winter Park, Florida

19. The Alfond Inn

This upscale yet family-friendly boutique hotel offers spacious rooms and suites, a beautiful courtyard, outdoor pool, and proximity to Park Avenue.

20. Hilton Garden Inn Winter Park

The Hilton Garden Inn Winter Park is conveniently located near I-4 and offers connecting rooms and an on-site restaurant. The hotel is within walking distance of several restaurants and shopping at Winter Park Village.

21. Park Plaza Hotel

A historic boutique hotel with a warm, welcoming atmosphere, Park Plaza Hotel is located right on Park Avenue and is a charming place to stay for families visiting Winter Park.

22. SpringHill Suites by Marriott Winter Park

SpringHill Suites Winter Park offers spacious, affordable rooms and a convenient location along North Orlando Avenue, making it a great choice for a stress-free vacation. Enjoy amenities like complimentary breakfast and free wifi.

Winter Park lights up at night during the Christmas season. Photo courtesy City of Winter Park

Fun Winter Park Events for Families

23. Christmas in Winter Park

During the holiday season, Winter Park hosts several festive events, including Christmas in the Park, Winter on the Avenue, and the Ye Olde Hometown Christmas Parade.

24. Popcorn Flicks in the Park

On select months, grab a blanket and snacks to enjoy a free movie in Central Park.

25. Unity Heritage Festival

This annual festival celebrates the life of Dr. Martin Luther King, Jr. and promotes community and family heritage.

Enjoy the Winter Park 4th of July Celebration. Photo courtesy City of Winter Park

26. Winter Park 4^th of July Celebration

Kids will love decorating their bicycle to participate in the annual bicycle parade! This event also includes a free kids zone, live music, and more.

27. Winter Park Sidewalk Art Festival

One of the nation’s top art festivals, this annual event features live entertainment, food vendors, and a special children’s area with interactive art activities.