Winter Haven, FL 4-5

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Winter Haven is a vibrant city that offers a unique blend of small-town charm and exciting attractions. Known as the “Chain of Lakes City,” Winter Haven boasts an impressive 50 lakes within or bordering its city limits, with 24 of these lakes connected by navigable canals, creating a paradise for water enthusiasts.

The city’s history dates back to the early 1880s when it began to develop around the Plant System railroad. Originally called Harris Corners, it was officially incorporated as Winter Haven in 1911. The 1920s brought a significant boom to the area, with many colonial revival homes being built during this period. Today, more than 50 of these historic homes are listed on the National Register of Historic Places, and the city features four distinct historic districts, including its charming downtown area.

Winter Haven’s most famous landmark is undoubtedly LEGOLAND Florida Resort, which opened in 2011 on the former site of Cypress Gardens. This beloved theme park, which operated from 1936 to 2009, was once known as the “Water Ski Capital of the World” and drew tourists from all over the country. Today, LEGOLAND preserves key elements of Cypress Gardens’ legacy while offering more than 50 rides, shows, and attractions for families with children. Adjacent to LEGOLAND is the newer Peppa Pig Theme Park, designed specifically for preschoolers. Next article.

The Chain of Lakes is the heart of Winter Haven’s recreational offerings. Visitors can rent pontoon boats, kayaks, or paddleboards to explore the interconnected waterways. The Living Water Boat Cruises offers guided tours through the scenic chain, providing a relaxing way to enjoy the natural beauty. For the more adventurous, wakeboarding and water skiing opportunities abound, continuing the city’s storied water sports tradition. The Cypress Gardens Water Ski Team still performs monthly shows on Lake Silver, honoring the city’s aquatic heritage.

Downtown Winter Haven has undergone a renaissance in recent years, with a thriving arts and culture scene. The Historic Ritz Theatre and Gram Parsons Derry Down venue host live performances throughout the year. Theatre Winter Haven, acclaimed as “one of the best community theaters in America,” offers high-quality productions from September through April. Art galleries and interactive artistic experiences dot the downtown landscape.

Food enthusiasts will delight in Winter Haven’s culinary offerings. Lakeside dining at Harborside Restaurant or Harry’s Old Place provides scenic views with delicious meals. Andy’s Igloo, a family favorite since 1951, serves classic American fare including their famous “Garbage Can” milkshakes. For craft beer lovers, Grove Roots Brewing Co. and Union Taproom offer locally brewed options in relaxed settings. Coffee aficionados can enjoy a cup at Richard’s Fine Coffee, Honeycomb Bread Bakers, or Haven Coffee Roasters, which roasts beans on-site.

Shopping opportunities range from antique hunting at Sherman’s Antiques to outdoor gear at Andy Thornal Company, often described as a boutique version of REI. The city’s retail scene focuses on unique, locally-owned businesses rather than chain stores.

Beyond the city limits, Winter Haven serves as an excellent base for exploring other Central Florida attractions. Bok Tower Gardens in nearby Lake Wales offers historic gardens and a singing tower carillon. The mysterious Spook Hill, where objects appear to roll uphill against gravity, provides a quirky roadside attraction.

Winter Haven embodies the perfect balance of recreation, culture, and small-town Florida charm. Whether you’re gliding across its interconnected lakes, building memories at LEGOLAND, or simply enjoying a sunset with a locally brewed beer, this Central Florida gem offers a refreshing alternative to the busier tourist destinations nearby.