20 Best & Fun Things to Do in Winter Haven, FL

Nestled in the heart of Polk County, Florida, Winter Haven is a city where the charm of old Florida meets vibrant, family-friendly fun. Known affectionately as the “Chain of Lakes City,” this picturesque destination boasts a unique atmosphere, where moss-draped cypress trees line tranquil waterways and the sun always seems to shine a little brighter.Â

With a rich history steeped in citrus farming and the legacy of Cypress Gardens, Winter Haven offers a captivating blend of natural beauty, cultural heritage, and thrilling attractions.

Once a quiet agricultural hub, Winter Haven has blossomed into a bustling city with a population that embraces its lakeside lifestyle. Its allure lies in its ability to cater to diverse interests, from exhilarating theme park adventures to serene nature escapes and fascinating historical discoveries.Â

This comprehensive guide is your passport to uncovering the 20 best and most fun things to do in Winter Haven, ensuring an unforgettable journey through this enchanting Floridian gem.

Things to Do in Winter Haven, FL

1. LEGOLAND Florida Resort

LEGOLAND Florida Resort is the ultimate destination for families with children aged 2-12, offering a world of creativity, fun, and adventure. Built on the historic site of Cypress Gardens, the park seamlessly blends the charm of the past with the excitement of LEGO-themed rides and attractions. It’s a place where imaginations run wild and childhood dreams come to life.

Beyond the thrilling rides like The Dragon and Coastersaurus, you can explore interactive adventures such as LEGO NINJAGO The Ride and Lost Kingdom Adventure.

The park also features incredible LEGO creations, from miniature cities in Miniland USA to life-sized models of animals and characters. Don’t forget to check out the LEGOLAND Water Park for a refreshing splash on a hot Florida day.

For an even more immersive experience, consider staying at one of the on-site themed hotels, such as the LEGOLAND Hotel, Pirate Island Hotel, or the Beach Retreat, which offer unique LEGO-themed rooms and daily entertainment. Be sure to check their opening hours, as Water Park and Peppa Pig Theme Park hours may differ.

Address: 1 LEGOLAND Way, Winter Haven, FL 33884

2. Peppa Pig Theme Park Florida

Step into the whimsical world of Peppa Pig and her friends at the world’s first Peppa Pig Theme Park, located just steps away from LEGOLAND Florida Resort. This park is designed specifically for preschoolers and young children, offering gentle rides, interactive play areas, and live shows featuring beloved characters. It’s a colorful and engaging experience that will delight little ones.

Children can ride in Daddy Pig’s Car, soar high on Peppa Pig’s Hot Air Balloon, or splash around in Muddy Puddles Splash Pad. There are also plenty of opportunities for photo ops with Peppa, George, and their friends, making for truly memorable moments. The park is thoughtfully designed to be accessible and enjoyable for its youngest visitors.

The park offers various ticket options, often bundled with LEGOLAND admission, making it a great add-on for a multi-day family adventure. Check the park’s calendar for specific opening hours, as they can vary.

Address: 1 LEGOLAND Way, Winter Haven, FL 33884

3. The Chain of Lakes

Winter Haven truly lives up to its nickname as the “Chain of Lakes City” with its remarkable interconnected system of lakes. This natural marvel offers a tranquil setting for quiet reflection and a plethora of outdoor activities. It’s a serene escape from the hustle and bustle, providing endless opportunities to connect with nature.

Imagine a leisurely afternoon spent strolling along scenic pathways lined with lush greenery, or simply sitting by the water’s edge, watching the gentle ripples and occasional kayak glide by. The Chain of Lakes is perfect for swimming, fishing for bass, and exploring. Keep an eye out for local wildlife, including alligators, otters, and a variety of birds.

For those seeking a more active adventure, consider renting a kayak or paddleboard to explore the interconnected waterways at your own pace. Boat tours are also available, providing narrated journeys that delve into the history and ecology of this unique aquatic system.

Address: Winter Haven, FL

4. Living Water Boat Cruises

Experience true southern hospitality and explore the breathtaking beauty and rich history of Winter Haven’s famous Chain of Lakes with Living Water Boat Cruises. These award-winning boat tours offer an unparalleled perspective of the area’s natural wonders and historical significance, particularly as the former home of Cypress Gardens.

As you glide across the tranquil waters, narrated by local guides with over 40 years of experience, you’ll have the chance to spot diverse wildlife, including alligators, otters, turtles, bald eagles, and a variety of wading birds like Blue Herons and Pelicans. The tours are designed to be an adventure like no other, offering insightful commentary and stunning scenery.

Options include scenic day tours, romantic sunset cruises, and even exclusive reservations for dining at the Harborside restaurant. They also offer special event cruises, such as watching the Legoland fireworks on the 4th of July or celebrating birthdays and anniversaries on the water. Reservations are highly recommended, especially for popular times.

5. Bok Tower Gardens

Just a short drive from Winter Haven, in Lake Wales, lies the magnificent Bok Tower Gardens, a National Historic Landmark that offers a serene and awe-inspiring experience. This contemplative garden and bird sanctuary, designed by Frederick Law Olmsted Jr., is a true masterpiece of landscape architecture and a haven for nature lovers.

The focal point is the 205-foot Singing Tower, a Gothic Revival and Art Deco carillon tower that houses 60 bells. Daily carillon concerts fill the air with enchanting melodies, creating a truly magical atmosphere. Explore the winding paths, discover hidden nooks, and marvel at the diverse plant collections, including rare and endangered species.

Plan to spend at least half a day immersing yourself in the tranquility of the gardens. There’s also the Pinewood Estate, a historic Mediterranean-style mansion within the grounds, offering tours to glimpse into Florida’s past. The on-site café provides a pleasant spot for lunch with a view.

Address: 1151 Tower Blvd, Lake Wales, FL 33853

6. Downtown Winter Haven

Stroll through the charming downtown area of Winter Haven, where the nostalgic charm of “Small Town America” comes alive. This historic district boasts a unique blend of mid-century modern and turn-of-the-century architecture, exuding a distinct old-school Florida vibe. It’s a delightful place to explore on foot, with its quaint shops, inviting restaurants, and vibrant community feel.

Discover local boutiques offering unique finds, from clothing to gifts and outdoor gear. The downtown area is also home to the iconic First Publix, where grocery shopping becomes a piece of local history. Enjoy the southern charm as you meander along the streets, soaking in the relaxed atmosphere.

Many local events and festivals take place in downtown Winter Haven throughout the year, adding to its lively appeal. It’s a great spot for an afternoon coffee, a delicious meal, or simply to enjoy the friendly conversations and community spirit.

Address: Central Avenue and Main Street in Winter Haven.

7. Polk State College Winter Haven Art Gallery

For art enthusiasts, the Polk State College Winter Haven Art Gallery is a vibrant hub of creativity and cultural expression. Located on the Winter Haven campus, this community space regularly hosts changing exhibitions, showcasing a diverse range of artwork from both students and national or regional artists.

The gallery provides an inspiring environment to engage with the local art scene, whether you’re an aspiring artist or simply looking to appreciate creative works. Exhibitions feature various mediums, including drawing, painting, ceramics, sculpture, mixed media, photography, and digital media.

Check their calendar for upcoming exhibitions, artist talks, and special events. They often host student art exhibitions and competitions, offering a glimpse into emerging talent. The gallery is a testament to Winter Haven’s commitment to fostering artistic growth and appreciation.

Address: 999 Avenue H NE, Winter Haven, FL 33881

8. Winter Haven Farmer’s Market

For an authentic taste of local agriculture and artisan craftsmanship, head to the Winter Haven Farmer’s Market. Held every Saturday, this lively market is a celebration of the region’s bounty and a gathering place for the community. It’s a fantastic way to experience the local culture and support small businesses.

Here, you can find everything from freshly harvested produce and delicious baked goods to handmade crafts and unique culinary delights. The market often features live music, creating a warm and inviting atmosphere that encourages lingering and conversation.

It’s an ideal spot to pick up fresh ingredients for a picnic by the lake or to find a unique souvenir. Be sure to arrive early for the best selection, especially for popular items.

Address: 250 Magnolia Ave Ste 100, Winter Haven, FL 33880

9. Hand & Stone Massage and Facial Spa

After a day of exploring Winter Haven’s attractions, unwind and rejuvenate at Hand & Stone Massage and Facial Spa. This tranquil oasis offers a variety of soothing spa treatments designed to renew your skin and relieve stress. It’s the perfect place for some well-deserved self-care.

Choose from full-body therapeutic massages tailored to your ideal pressure, or indulge in facials and advanced skincare treatments designed specifically for your skin’s needs. Their licensed professionals combine skill with intention to provide a deeply relaxing and lasting impact.

They offer introductory pricing for first-time guests, making it an accessible option for a moment of calm. Whether you’re looking to soothe sore muscles, achieve glowing skin, or simply recharge your mind, Hand & Stone provides a customized and serene experience.

Address: 585 Cypress Gardens Blvd, Winter Haven, FL 33880

10. Theatre Winter Haven

Known as “one of the best community theatres in America,” Theatre Winter Haven has been inspiring, challenging, entertaining, and educating the community since 1970. This beloved cultural gem brings the magic of Broadway to life through an array of musicals, plays, and special events each year.

The theatre produces a five-play MainStage subscription season, a three-play youth series, a Professional Series, and numerous Tribute Tuesday Series events. Their new Blackbox theatre, the Norman and Linda Small Stage, opened in Fall 2022, providing a second performance space for more intimate connections between performers and audiences.

Attending a show at Theatre Winter Haven is a fantastic way to experience the local arts scene and enjoy high-quality theatrical productions. Be sure to check their schedule and book tickets in advance, especially for popular performances.

11. Museum of Winter Haven History

Delve into the rich past of Winter Haven by visiting the Museum of Winter Haven, a local treasure that offers fascinating insights into the area’s history. This museum is a must-visit for history buffs and anyone curious about the evolution of this charming Central Florida city.

The museum houses a collection of artifacts, photographs, and exhibits that showcase Winter Haven’s heritage, from its early days as a citrus and agricultural center to its development as a popular tourist destination with Cypress Gardens. You’ll learn about the people, industries, and events that shaped the community.

Exploring the museum not only deepens your understanding of Winter Haven’s cultural heritage but also provides a unique perspective on how the region has evolved over the years. Check their website for current exhibits and special events, which often highlight different aspects of local history.

12. Colt Creek State Park

For an immersive natural experience, take a day trip to Colt Creek State Park, located just north of Winter Haven. Spanning more than 5,000 acres, this park preserves a vast expanse of native Central Florida habitat, offering a glimpse into the “Real Florida” with its diverse ecosystems and abundant wildlife.

Explore over 15 miles of multi-use trails that wind through longleaf pine flatwoods, thick cypress domes, and open vistas. These trails are perfect for hiking, bicycling, and horseback riding. The park is home to a variety of species, including bald eagles, white-tailed deer, American alligators, otters, and numerous birds and butterflies. You might even spot threatened species like the gopher tortoise.

The park’s lakes are ideal for birdwatching, fishing from the accessible dock, or paddling. Colt Creek State Park also offers various camping experiences, including primitive, equestrian, and group campgrounds, for those looking to extend their nature escape.

Address:Â16000 State Rte 471, Lakeland, FL 33809

13. Harborside Restaurant

For a memorable dining experience with unparalleled views, visit Harborside Restaurant in Winter Haven. This establishment is Central Florida’s premier waterfront dining location, offering stunning vistas of Lake Shipp. It’s the perfect spot for a relaxed lunch or a romantic dinner.

Harborside specializes in fresh seafood, but also offers a variety of American classics and other dishes to suit every palate. The atmosphere is casual yet elegant, making it suitable for both family meals and special occasions. Enjoy watching boats pass by on the lake as you savor your meal.

Reservations are recommended, especially during peak dining hours or for waterside tables. Don’t miss the opportunity to dine al fresco on their patio to fully appreciate the beautiful lakeside setting.

Address: 2435 7th St SW, Winter Haven, FL 33880

14. Arabellas Ristorante

Located in Times Square, in the heart of historic downtown Winter Haven, Arabellas Ristorante offers an exquisite Italian and Mediterranean dining experience. Renowned for its elegant atmosphere and authentic cuisine, Arabellas is a staple for fine dining in the area.

The restaurant prides itself on using the freshest ingredients to create classic dishes with a contemporary touch. From pasta and seafood to succulent meat dishes, each plate is crafted with care and presented beautifully. The attentive service and inviting ambiance contribute to a truly special meal.

Enjoy a cocktail before or after dinner in their chic Ave Bar, and let their knowledgeable staff help you choose the perfect wine from their extensive selection to complement your meal. Arabellas also offers a private dining room for corporate meetings or special occasions.

15. Lake Howard Park

For those seeking a peaceful retreat and a taste of Winter Haven’s natural beauty, Lake Howard Park is a must-visit destination. This park features well-maintained trails that wind through diverse landscapes and along the picturesque shores of Lake Howard, one of the city’s beautiful Chain of Lakes.

As you stroll or bike along these trails, you’ll be captivated by the vibrant local flora and the soothing sounds of nature. The park also provides excellent opportunities for birdwatching and photography, making it an ideal spot for nature enthusiasts and casual visitors alike. It’s a wonderful place for a reflective walk or simply to enjoy the tranquility.

Lake Howard Park offers tranquil picnic spots, making it perfect for a leisurely afternoon outing. It’s a great example of Winter Haven’s commitment to preserving its natural spaces for public enjoyment.

Address: 2100 Lake Howard Dr SW, Winter Haven, FL 33880

16. Cypress Gardens

Though the iconic Cypress Gardens as a standalone attraction is no longer, its historical significance and natural beauty are still very much alive within LEGOLAND Florida Resort. The botanical gardens, with their majestic cypress trees draped in Spanish moss, remain a timeless part of the theme park.

Originally opened in 1936, Cypress Gardens was Florida’s first theme park, famous for its lush botanical gardens, elaborate water ski shows, and Southern belles. Today, visitors to LEGOLAND can still wander through these enchanting gardens, appreciate the historic charm, and even catch the Cypress Gardens Water Ski Team performing on Lake Eloise.

As you wander along the winding paths, you can still feel the echoes of its storied past. It’s a peaceful area within the bustling theme park, offering a moment of tranquility and a connection to Florida’s tourism heritage.

17. The Village Sampler

Nestled in Winter Haven, The Village Sampler is a charming treasure trove that beckons vintage enthusiasts and casual shoppers alike. This unique establishment offers a delightful journey through collectibles, antiques, and eclectic finds, making it a paradise for those who love to browse and discover.

Upon arrival, visitors are often greeted by an impressive coat of arms, hinting at the building’s rich history and adding to its distinctive character. Inside, you’ll find a wide array of items, from classic furniture and vintage clothing to quirky decor and unique gifts.

It’s the perfect place to spend an afternoon hunting for a one-of-a-kind souvenir or a special piece to add to your collection. The ever-changing inventory means there’s always something new to explore, making each visit a fresh adventure.

Address: 155 Ave B SW, Winter Haven, FL 33880

18. Central Park

For a pleasant outdoor experience just a short drive from Winter Haven, visit Central Park in nearby Haines City. This well-maintained park offers a refreshing green space perfect for relaxation, recreation, and family fun.

Central Park features open grassy areas ideal for picnics, playing catch, or simply unwinding under the Florida sun. It often hosts local events and community gatherings, adding to its vibrant atmosphere. The park provides a great opportunity to enjoy the outdoors in a quiet, friendly setting.

With its accessibility and welcoming environment, Central Park is a convenient spot for a leisurely stroll, some fresh air, or a family outing. It’s a nice alternative to more crowded attractions, offering a slice of local life.

Address: 1501 W Commerce Ave, Haines City, FL 33844

19. Hope Presbyterian Church

Beyond its spiritual significance, Hope Presbyterian Church offers a glimpse into Winter Haven’s community history and architectural evolution. Established in 1958, this church has grown with the city, and its buildings reflect different periods of development and design.

The church’s story includes its early beginnings in Winter Haven High School, the dedication of its original educational unit in 1961, and the construction of its breathtaking sanctuary facing Lake Roy in 1980. The sanctuary features a huge Celtic Cross designed and carved by a member, and a unique Franz Heissler Organ.

Hope Church has a rich history of community involvement and mission work. Visitors interested in local history or architecture might appreciate a quiet moment to observe the grounds and the significant structures within.

20. SOUL Haven Ranch

For a truly unique and enchanting experience, step back in time with a horse-drawn carriage tour from SOUL Haven Ranch. While the specific address might be slightly outside Winter Haven’s immediate city limits, these tours offer a charming and memorable way to explore the surrounding natural beauty and rural landscapes.

These tours provide a romantic and peaceful journey, allowing you to relax and take in the scenery at a leisurely pace. They are particularly popular during the holiday season, with special Holiday Carriage Tours and Christmas Eve Carriage Tours that create a magical atmosphere.

Reservations are essential, especially for seasonal events, as these unique experiences are often in high demand. It’s a wonderful activity for couples, families, or anyone looking for a different kind of outdoor adventure.

Conclusion

Winter Haven, Florida, is a destination that truly has it all. From the exhilarating rides of world-class theme parks to the serene beauty of its interconnected lakes and lush botanical gardens, the city offers an unparalleled blend of adventure and tranquility. Its rich history, vibrant arts scene, and welcoming community create an atmosphere that is both captivating and comforting.

Whether you’re seeking family fun, a romantic getaway, or a peaceful escape into nature, Winter Haven delivers. Explore its historic downtown, savor delectable cuisine, discover hidden gems, and immerse yourself in the natural wonders that define this unique Floridian city. So pack your bags, bring your sense of adventure, and prepare to create unforgettable memories in the heart of Polk County. Winter Haven is waiting to charm you with its undeniable allure.