10 Things to Do in Winter Park Florida With Kids

You’ll find endless family fun in Winter Park with scenic pontoon boat tours through lakes and jungle-like canals where kids can spot alligators and herons. Explore the whimsical Castle Playground, browse the charming Saturday Farmers’ Market, and let little ones run free at Winter Park Village’s outdoor spaces. Don’t miss storytimes at the library, hands-on art experiences at the Morse Museum, and over 150 free family events throughout the year that’ll keep everyone entertained and create lasting memories.

Take a Scenic Boat Tour on the Winter Park Chain of Lakes

When you’re looking for a gentle adventure that’ll captivate kids of all ages, Winter Park’s scenic boat tours deliver the perfect blend of excitement and relaxation. Your hour-long pontoon journey winds through three stunning lakes and two narrow canals, creating a “jungle tunnel” experience kids absolutely love.

Watch their eyes light up spotting herons, cranes, and occasional alligators while learning fascinating local history and nature facts from knowledgeable guides.

The 18-passenger boats operate daily from 10 a.m. to 4 p.m., departing roughly every hour. At $20 for adults and $10 for children (ages 2-11), it’s budget-friendly family fun.

Since it’s first-come, first-served, arrive early on weekends. For larger families or groups traveling together, you can call ahead at 407-644-4056 to ensure availability. The slow, steady pace ensures even motion-sensitive kids stay comfortable throughout this memorable Winter Park experience.

Explore Central Park and Stroll Down Park Avenue

Right in downtown Winter Park’s heart, Central Park offers families the perfect blend of natural beauty and urban excitement that’ll keep your kids engaged for hours. The park’s lush landscaped gardens and open green spaces create an ideal playground for picnics under swaying palms and towering cypress trees.

Your children will love running through the rose garden while you enjoy the relaxing atmosphere. In March, families can stroll beneath the park’s picturesque arbor adorned with blooming purple wisteria for a truly enchanting experience.

Just steps away, Park Avenue beckons with over 140 boutiques, sidewalk cafes, and galleries perfect for family strolling. The leafy walkways provide shade as you explore this upscale shopping district.

Don’t miss special events like the Pancake Breakfast before the Christmas Parade or the Olde Fashioned 4th of July Celebration that create magical memories for kids of all ages.

Visit the Saturday Farmers’ Market at the Historic Train Depot

Just a short walk from Park Avenue’s bustling shops, the Saturday Farmers’ Market at the Historic Train Depot transforms into a treasure hunt your kids will absolutely love. Every Saturday from 8 a.m. to 1 p.m., this charming outdoor market at Central Park West Meadow offers the perfect family adventure.

Your children can explore 20-25 stalls filled with fresh produce, handmade donuts, popcorn, and acai bowls while you browse local honey and artisanal breads. The compact layout means you’ll cover everything in about 30 minutes, perfect for little attention spans.

Kids love the small-town atmosphere and open-air setting. The market’s strong reputation is reflected in its impressive 4.6 rating based on over 1,300 reviews from satisfied visitors.

After shopping, head to nearby Central Park’s grassy areas for snack breaks and playtime, making this a complete morning experience.

Play at Winter Park Village’s Outdoor Entertainment Center

Where can you find the perfect blend of shopping, dining, and outdoor play all in one convenient spot? Winter Park Village’s open-air entertainment center delivers exactly that! Your kids will love running around the central lawn and plaza area while you browse shops or grab a bite.

The wide pedestrian walkways make stroller navigation a breeze, and shaded seating areas let you supervise playtime comfortably.

Catch a family-friendly movie at the Cobb theater, then let the kids burn energy in the green spaces afterward. The outdoor format feels less overwhelming than traditional malls, creating a relaxed atmosphere for families.

With seasonal events, holiday decorations, and easy access to treats like ice cream, Winter Park Village keeps children entertained while parents tackle their shopping lists efficiently. The location offers convenient access to Orlando International Airport, just 18 miles away for families traveling from out of town.

Discover the Castle Playground and Community Parks

When your little ones need space to set free their imaginations, Martin Luther King Jr. Park’s Castle Playground delivers adventure in spades. This iconic wooden castle structure, designed by nationally renowned Robert Leathers, has captivated kids for over 30 years with its maze-like layout of towers, bridges, tunnels, and slides.

Your children can pretend they’re conquering castles or sailing pirate ships while maneuvering multiple climbing elements suited for toddlers through elementary ages. The playground includes various swings, including adaptive options and tire swings, ensuring every child can participate.

The surrounding 23-acre park enhances your visit with sports fields, a half-mile paved walking loop around a scenic lake, exercise equipment, picnic pavilions, and restrooms. Large parking areas and shaded spots under mature oaks make this Winter Park’s ultimate family destination. Exciting playground renovations are currently underway to enhance safety standards and incorporate community feedback into new play areas and improved infrastructure.

Wander Through Mead Botanical Garden’s Nature Trails

While your kids might think they need exotic destinations for adventure, Mead Botanical Garden’s 47-acre wonderland delivers exciting nature discoveries right in Winter Park’s backyard. You’ll find easy, interconnected trails perfect for little legs, including the scenic Lake Lillian boardwalk that zigzags over marshes where you might spot turtles, wading birds, or even alligators from safe viewing areas.

The typical family loop covers about a mile through diverse habitats—from shaded live oaks to cypress swamps—keeping curious minds engaged. Your children can listen for birds, toss leaves from bridges, and explore butterfly gardens that attract hummingbirds. The garden’s tall pine trees create natural shade and add to the peaceful atmosphere as you explore the winding creek and various ecosystems.

With free admission, restrooms, picnic areas, and wheelchair-accessible paths, you’ve got everything needed for budget-friendly nature education that feels like pure adventure.

Experience Art at the Morse Museum and Polasek Sculpture Gardens

After exploring nature’s wonders, you can spark your children’s creativity at two incredible art destinations that make Winter Park a cultural treasure.

The Morse Museum houses the world’s most extensive collection of Louis Comfort Tiffany works, featuring dazzling stained glass windows, colorful lamps, and the spectacular Tiffany Chapel from the 1893 World’s Fair. Your kids will be mesmerized by the glowing glass artworks and immersive galleries recreating rooms from Tiffany’s mansion.

Take advantage of free Friday night admission with live music, summer family programs, and free audio tours designed for young visitors.

Next door, the Polasek Sculpture Gardens offers outdoor art exploration where children can discover fascinating sculptures while enjoying fresh air and beautiful gardens. The gardens showcase the legacy of Albin Polasek, a remarkable artist who continued creating representational sculptures even after learning to sculpt with one hand following a stroke.

Enjoy Story Time and Programs at Winter Park Library

Several engaging programs at Winter Park Library transform reading into an interactive adventure that’ll captivate your little ones while fostering their love for books. The Bouncing Babies Program creates perfect bonding time for infants through bouncing and interactive activities every December 23rd from 9:15-10:00 am.

Your two-year-olds will love Tales for Twos, featuring age-appropriate stories designed specifically for their developmental stage.

Story Sacks offer monthly surprises for ages 3-9, combining books with hands-on activities that bring stories to life. You’ll need to sign up in advance for this popular program. The library also hosts special themed events throughout the year that add variety to their regular programming schedule.

All library story times are completely free and strategically scheduled throughout the week. These programs provide structured literacy experiences while giving you quality time with your children in Winter Park’s welcoming community space.

Attend Seasonal Festivals and Holiday Celebrations

Winter Park transforms into a magical wonderland during the holiday season, offering families countless opportunities to create lasting memories together.

Your kids will love Winter on the Avenue, where Park Avenue closes to traffic for tree lighting, Santa visits, snow slides, and s’mores from 5–9 p.m.

The multicultural celebration includes Christmas trees, Menorah lighting, and Kwanzaa displays in Central Park.

Don’t miss Popcorn Flicks in the Park, screening family-friendly holiday movies outdoors on a giant screen.

The free Holiday Pops concert features the Orlando Philharmonic performing carols you can sing along to—bring chairs and picnic dinners!

For indoor entertainment, catch Orlando Ballet’s The Nutcracker at Dr. Phillips Center or explore designer-decorated trees at the Festival of Trees. Just a short drive away in nearby Winter Garden, families can enjoy horse-drawn carriage tours through the historic downtown area decorated for the holidays.

Participate in the City’s Free Family Fun Program Events

Your family can easily tap into Winter Park’s incredible Free Family Fun Program, which has delivered over 150 no-cost events since 2018 specifically designed to get kids outdoors and engaged.

You’ll discover park-based activity days with group games, creative craft sessions, nature exploration adventures, and movie nights across the city’s beautiful parks. The program emphasizes “unplugged” quality time while showcasing Winter Park’s amazing park system, from Central Park’s oak-shaded lawns to neighborhood gems with castle-style playgrounds.

Check the City of Winter Park’s event calendar or follow @ParksandRecWP on social media for upcoming dates and locations. Events welcome both residents and visitors, requiring no registration fees. These activities help foster closer bonds between family members through shared outdoor experiences.

Bring blankets, chairs, and water bottles for maximum comfort during these fantastic family adventures.

The Sum Up

You’ll never run out of amazing adventures in Winter Park! From splashing around the lakes to discovering incredible art, there’s something magical waiting around every corner. Your kids will love the playgrounds, festivals, and all the hands-on fun this charming city offers. Pack your sense of wonder and get ready to create unforgettable family memories. Winter Park’s calling – it’s time to explore and make every moment count!