Winter Haven, FL 4-8

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Winter Haven has established itself as a vibrant community known for its natural beauty, rich history, and unique attractions. This charming city, aptly named for being a peaceful refuge from harsh northern winters, offers a perfect blend of small-town charm and modern amenities that appeal to both residents and visitors alike.

A History Woven Through Water

Winter Haven’s story begins in the late 19th century when pioneers started settling in the area. Before this time, the region was primarily inhabited by Native American tribes, including the Seminoles. The first significant land ownership came through the Florida Land and Colonization Company, formed by British entrepreneurs.

By the 1880s, families like the Harris and Eycleshimer had arrived from Vermont and New York, establishing camps near the local lakes. F.A.K. Harris built the first structure in what would become downtown Winter Haven, initially called Harris Corners in his honor. It was Peter Eycleshimer who eventually suggested the name “Winter Haven,” envisioning the area as a winter resort destination. See next article.

The city’s official incorporation came on May 26, 1911, with a population of around 400 residents. By then, Winter Haven boasted citrus groves, a school, a post office, churches, hotels, and even its own newspaper. The introduction of interconnected canals linking the city’s numerous lakes began in 1915 with the formation of the Twenty Lakes Boat Course Club, creating what would become one of the city’s most distinctive features.

The Cypress Gardens Legacy

No discussion of Winter Haven would be complete without highlighting Cypress Gardens, Florida’s first commercial tourist attraction. Opened on January 2, 1936, by Dick and Julie Pope, this botanical garden on the shores of Lake Eloise transformed Winter Haven into a tourism destination and shaped its identity for decades.

In 1943, the park introduced its first water ski show to entertain visiting servicemen, quickly establishing Winter Haven as the “water ski capital of the world” – a distinction the city still proudly claims today. By the late 1940s and through the 1960s, Cypress Gardens had become a Hollywood favorite, with stars like Elvis Presley, Esther Williams, and Johnny Carson visiting the park. Films such as “Easy to Love” and “On an Island With You” were shot on location, further cementing its fame.

Though Cypress Gardens closed in 2009 after changing ownership multiple times and weathering economic challenges, its legacy lives on. Today, the grounds are home to LEGOLAND Florida Resort, which preserved many elements of the original gardens, including the iconic Banyan tree planted in 1939 and water ski shows featuring LEGO pirates.

The original Cypress Gardens Water Ski Team continues the tradition with monthly shows on Lake Silver, keeping this important part of Winter Haven’s heritage alive for new generations.

The Chain of Lakes: Winter Haven’s Crown Jewel

Perhaps Winter Haven’s most distinctive natural feature is its impressive Chain of Lakes – a connected system of freshwater lakes that defines the city’s geography and lifestyle. This aquatic network creates endless opportunities for recreation and has shaped the community’s identity as a lakeside paradise.

The Chain of Lakes consists of two main groups – the Northern Chain with 10 lakes and the Southern Chain with 16 lakes, all connected by a series of navigable canals. These waterways allow boaters to travel between lakes without having to trailer their vessels, creating one of Florida’s most unique aquatic environments.

For locals and visitors alike, the lakes offer year-round recreation. Pontoon boat cruises with companies like The Living Water Boat Cruises provide guided tours of the chain. Adventurous souls can explore via kayak rentals from Off the Chain Kayak Co., try paddleboarding with Paddleboard Winter Haven, or experience wakeboarding and tubing with Central Florida Watersports.

The lakes also serve as gathering places for community events, most notably the annual Chain of Lakes Christmas Boat Parade. This beloved holiday tradition features decorated boats traveling from Lake May to Lake Howard and Lake Shipp, with viewing areas at lakeside restaurants and establishments.

A Community of Culture and Recreation

Beyond its natural beauty, Winter Haven boasts a surprisingly rich cultural scene for a city of its size. Theatre Winter Haven has earned national acclaim as one of America’s best community theaters, featuring performances from September through April, with alumni including Tony Award winner Karen Olivo.

The historic downtown district has undergone significant revitalization and now features art galleries, locally-owned restaurants, and unique shops. Musical heritage is preserved at venues like Gram Parsons’ Derry Down and the historic Ritz Theatre, keeping the city’s creative spirit alive.

For families, LEGOLAND Florida Resort and the adjacent Peppa Pig Theme Park have become major attractions, drawing visitors from across the country. These parks, built on the former Cypress Gardens property, honor the site’s heritage while bringing new energy to the community.

Culinary enthusiasts can enjoy lakeside dining at establishments like Harborside Restaurant or explore the local craft beer scene at Grove Roots Brewing Co. Traditional Florida favorites like Andy’s Igloo serve up classic burgers and their famous “Garbage Can” milkshakes, while Harry’s Old Place offers fresh seafood delicacies including pecan-crusted grouper.

Seasonal events like Starlight Nights Downtown, a six-week festival of lights celebrating the holidays, and Carols in the Park showcase the community’s festive spirit. The winter months bring an influx of seasonal residents escaping colder climates, adding to the city’s dynamic energy.

Looking to the Future While Honoring the Past

Today’s Winter Haven balances its historical roots with forward-looking development. The city has embraced its identity as a water recreation destination while diversifying its economy and cultural offerings. The preservation of landmarks like the Banyan tree at LEGOLAND and continued traditions like the water ski shows demonstrate a commitment to honoring the past.

For those discovering Winter Haven for the first time, the city offers an authentic slice of Central Florida charm away from the larger tourist centers. Whether watching a vibrant orange and pink sunset from a lakeside dock, exploring the Chain of Lakes by boat, or enjoying a performance at Theatre Winter Haven, visitors find themselves embraced by a community that values both natural beauty and cultural richness.

Winter Haven truly lives up to its name – a welcoming haven in the heart of Florida where lakes, history, and community spirit create a distinctive destination worth experiencing in every season.