Winter Haven, FL

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Winter Haven is a vibrant city that combines small-town charm with an abundance of recreational opportunities. Known as the “Chain of Lakes City,” Winter Haven lives up to its name with 50 lakes within or bordering its city limits, creating a paradise for water enthusiasts and nature lovers alike.

A Rich History

Winter Haven’s story began shortly after Florida became a state in 1845, when pioneers started settling in the area previously inhabited by Native American tribes, including the Seminoles. The first deeded land owners were a group of Englishmen who formed the Florida Land and Colonization Company, Ltd. By the 1880s, more settlers had arrived, including the Harris and Eycleshimer families from Vermont and New York.

Originally called Harris Corners after F.A.K. Harris, who built the first building downtown, the city was renamed Winter Haven in 1911 by Peter Eycleshimer, who envisioned creating a winter resort. That same year, Winter Haven was officially incorporated as a town with a population of around 400 residents, boasting citrus groves, a school, a post office, churches, hotels, and even 15 automobiles. Another article.

The 1920s Florida land boom brought significant growth, and a pivotal moment in the city’s development came on September 6, 1930, when 22-year-old George Jenkins opened the first Publix Super Market on Fourth Street. In 1936, Dick and Julie Pope opened Cypress Gardens, putting Winter Haven on the map as a tourist destination.

A Thriving Community

Today, Winter Haven is the second most populated city in Polk County with over 52,800 residents as of 2023, showing steady growth of more than 4% from the previous year. The population is diverse, with approximately 44% White (non-Hispanic), 25.7% Black or African American, and 24.6% Hispanic residents.

The median age of Winter Haven residents is 40.6 years, and the median household income stands at $59,604, showing a 5.63% increase from 2022. With a homeownership rate of 62.3% and a median property value of $248,200, Winter Haven offers an affordable alternative to Florida’s more expensive coastal cities.

Attractions and Recreation

Winter Haven is perhaps best known as the home of LEGOLAND Florida Resort, built on the former site of Cypress Gardens. This family-friendly theme park attracts visitors from across the country and includes a water park designed specifically for children aged two to twelve.

More recently, the Peppa Pig Theme Park opened just steps from LEGOLAND, providing additional entertainment options for families with young children.

However, Winter Haven’s natural attractions are equally impressive. The city’s Chain of Lakes includes 16 lakes connected by navigable canals, offering endless opportunities for boating, fishing, kayaking, and paddleboarding. Visitors can explore the lakes through various tour options, including pontoon boat cruises with The Living Water Boat Cruises or kayak rentals from Off the Chain Kayak Company.

As the “Water Ski Capital of the World,” Winter Haven maintains its connection to this sport through performances by the Cypress Gardens Water Ski Team, who showcase their skills on Lake Silver monthly.

Arts, Culture, and Dining

Winter Haven boasts a rich cultural scene centered around its historic downtown area. Theatre Winter Haven has earned national recognition as “one of the best community theaters in America,” offering quality performances from September through April. The Historic Ritz Theater and Gram Parsons Derry Down provide additional venues for arts and entertainment.

The dining scene in Winter Haven reflects its diverse community, with options ranging from upscale establishments like Nutwood and Arabellas to casual waterfront eateries such as Harborside and Harry’s Old Place. Grove Roots Brewing Co. offers craft beers in a family-friendly setting, while Andy’s Igloo has been serving burgers, fries, and milkshakes since 1951.

For those interested in exploring multiple culinary offerings, Winter Haven Food Tours provides guided experiences through the city’s food scene.

Looking Ahead

Winter Haven continues to evolve while maintaining its lakeside charm. Recent development projects like Bowen Yard, a new food and event space featuring six eateries, demonstrate the city’s commitment to growth and innovation.

With its unique blend of natural beauty, family-friendly attractions, cultural offerings, and strong sense of community, Winter Haven stands as a testament to thoughtful development and quality of life. Whether you’re seeking a weekend getaway or a place to call home, this Central Florida gem offers a warm welcome true to its name—a haven in any season.