Winter Haven, FL 4-2
About an hour southwest of Orlando, Winter Haven offers a unique blend of small-town charm and vibrant attractions. This picturesque city, known as the “Chain of Lakes City,” has transformed from humble beginnings to become a must-visit destination for families and outdoor enthusiasts alike.
A Rich Historical Tapestry
Winter Haven’s story begins with the Timucua and Calusa Native American tribes who originally inhabited the region before European colonization. In the 1840s, government surveyors like Henry Washington and Dr. John Westcott began mapping the area, leading to the first European settlements in the 1860s.
Originally called “Harris Corners” after local merchant F.A.K. Harris who built the first downtown building in 1884, the area was later renamed Winter Haven because of its pleasant climate. The city was officially incorporated as a town on June 22, 1911, and later reincorporated as a city on November 27, 1923, reflecting its growth and development.
The arrival of the railroad built by Henry Haines in 1883 significantly boosted the city’s commerce and settlement. By 1915, Winter Haven began constructing a series of canals connecting its numerous lakes, which helped transport citrus crops and established the foundation for what would become its iconic Chain of Lakes. Read another article.
The Water Ski Capital of the World
With 50 lakes within or bordering its city limits, Winter Haven has earned the title “Water Ski Capital of the World.” The banks of Lake Eloise, once home to the historic Cypress Gardens (Florida’s first theme park opened in 1936), became central to the development of water skiing as a sport.
Today, visitors can watch the original Cypress Gardens Water Ski Team perform on Lake Silver, typically on the third Saturday of each month. The Water Ski Museum and Hall of Fame celebrates the sport’s evolution and champions through memorabilia, photographs, and historical information.
LEGOLAND Florida: A New Era of Tourism
In October 2011, Winter Haven experienced a tourism renaissance when LEGOLAND Florida opened on the former site of Cypress Gardens. This 150-acre interactive theme park beautifully blends history with modern entertainment by incorporating elements of the historic gardens into its attractions.
Designed primarily for children ages 2-12, LEGOLAND features more than 50 rides, shows, and attractions, including a water park. The resort has expanded to include three themed accommodations: LEGOLAND Hotel, LEGOLAND Beach Retreat, and Pirate Island Hotel.
Adding to family entertainment options, the Peppa Pig Theme Park opened in 2022 just steps away from LEGOLAND. This park is specifically designed for preschoolers, featuring rides and attractions based on the beloved children’s TV show.
Outdoor Recreation and Natural Beauty
Winter Haven’s Chain of Lakes offers endless recreational opportunities. Visitors can explore the interconnected lakes via pontoon boat tours with The Living Water Boat Cruises, rent kayaks from Off the Chain Kayak Co., or try paddleboarding with Paddleboard Winter Haven.
For more adventurous water enthusiasts, tubing and wakeboarding are available through Central Florida Watersports. Fishing enthusiasts flock to the lakes for bass fishing, while nature lovers enjoy bird watching along the shores.
Cultural Scene and Downtown Vibrancy
Winter Haven boasts a surprisingly rich cultural scene. Theatre Winter Haven has been called “one of the best community theaters in America” and features performances from September through April.
The Historic Ritz Theater and Gram Parsons Derry Down venue showcase musical performances, while multiple art galleries and interactive artistic experiences dot the downtown area. The restored historic downtown business district features locally-owned artisan restaurants and boutique shopping.
Food enthusiasts can sample local flavors on a culinary journey with Winter Haven Food Tours or visit popular eateries like Harborside Restaurant for lakeside dining, Andy’s Igloo (a family favorite since 1951) for classic American fare, or Grove Roots Brewing Co. for craft beer.
Climate and Community
Winter Haven lives up to its name with a pleasant climate that attracts visitors year-round, especially those escaping harsh northern winters. The subtropical weather allows for outdoor activities throughout the year, though summers can be hot and humid with afternoon thunderstorms typical of Central Florida.
Community events regularly bring together residents and visitors alike, celebrating the city’s heritage, arts, and lakeside lifestyle. The area continues to develop while maintaining its small-town charm and connection to nature.
Winter Haven’s strategic location—just 30 miles from Walt Disney World and 18 miles from Bok Tower Gardens in Lake Wales—makes it an ideal base for exploring Central Florida beyond the major tourist hubs.
From its humble beginnings to its current status as a family-friendly destination, Winter Haven exemplifies the best of Central Florida: natural beauty, recreational opportunities, family attractions, and a vibrant community spirit—all centered around its beautiful Chain of Lakes.
Learn more about the city of Winter Haven, Florida.
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POI #2 – AutoZone Auto Parts, 3500 Havendale Blvd, Winter Haven, FL 33881