Winter Haven, FL 4-3
Between Tampa and Orlando in Central Florida lies Winter Haven, a charming city that offers a perfect blend of family attractions, natural beauty, and small-town charm. Known as the “Chain of Lakes City,” Winter Haven has evolved from its humble beginnings as a citrus farming community in the 1880s into a vibrant destination that attracts visitors from across the globe.
A Rich History
Winter Haven’s story began during Florida’s land boom of the early 20th century when it developed into a tourist destination. The city gained historical significance as the home of the first Publix supermarket, opened by George W. Jenkins in 1940, which has since grown into a major grocery chain throughout the Southeastern United States.
However, Winter Haven truly found its place on the map with the opening of Cypress Gardens in 1936, Florida’s first commercial tourist attraction. The botanical gardens, with their winding paths and towering cypress trees, became renowned for spectacular water ski shows that established Winter Haven as “The Water Ski Capital of the World.” Dick Pope Sr., Cypress Gardens’ founder, is often credited with popularizing water skiing as a professional sport, hosting numerous championships and fostering world record holders. Read next article.
The Chain of Lakes
Perhaps Winter Haven’s most distinctive natural feature is its impressive network of lakes. With 50 lakes within or bordering its city limits, the Chain of Lakes offers endless opportunities for recreation. Connected by navigable canals, these lakes form two main chains – the Southern Chain with 16 lakes and the Northern Chain with 5 lakes.
Visitors can explore these pristine waters in numerous ways: rent a pontoon boat from Marine Supply, take guided tours with The Living Water Boat Cruises, kayak with Off the Chain Kayak Company, or try paddleboarding with Paddleboard Winter Haven. Fishing enthusiasts flock to these waters for the excellent bass fishing, while nature lovers appreciate the abundant wildlife and waterfront views.
LEGOLAND Florida Resort
While Cypress Gardens may have put Winter Haven on the tourist map, today LEGOLAND Florida Resort serves as the city’s premier attraction. Built on the former Cypress Gardens site, LEGOLAND preserved the historic botanical gardens while creating a colorful theme park paradise for families with children.
The resort features over 50 rides, shows, and attractions spread across themed areas like LEGO NINJAGO World, LEGO City, and MINILAND USA. Water enthusiasts can enjoy LEGOLAND Water Park, while the whole family will appreciate the park’s commitment to preserving Cypress Gardens’ legacy, including the famous Banyan tree planted as a seedling in 1939.
For those wanting the full LEGO experience, the resort offers three unique accommodations: LEGOLAND Hotel, Pirate Island Hotel, and LEGOLAND Beach Retreat. In 2022, the Peppa Pig Theme Park opened adjacent to LEGOLAND, providing additional entertainment for preschool-aged visitors.
Downtown Charm and Cultural Delights
Winter Haven’s downtown district has undergone a renaissance in recent years, offering a pedestrian-friendly area filled with shops, restaurants, and cultural venues. Theatre Winter Haven, nationally acclaimed as “one of the best community theaters in America,” provides year-round performances from September through April.
Music lovers can visit the historic Gram Parsons Derry Down, a venue dedicated to nurturing local musicians, while the restored Ritz Theatre hosts various performances and events. Art enthusiasts can explore multiple galleries showcasing local talent, continuing the city’s long tradition of supporting the arts through organizations like the Ridge Art Association, which has promoted local artists since 1950.
Culinary Adventures
Winter Haven’s dining scene offers something for every palate, from waterfront eateries to beloved local institutions. Harborside Restaurant provides lakeside dining with spectacular views, while Harry’s Old Place serves up fresh seafood that keeps locals coming back for decades.
For a nostalgic treat, Andy’s Igloo has been serving burgers, fries, and their famous “Garbage Can” milkshake since 1951. Craft beer enthusiasts can sample local brews at Grove Roots Brewing Co. or visit Union Taproom, Polk County’s first self-pour taproom featuring 40 rotating taps. Coffee lovers can get their fix at establishments like Richard’s Fine Coffee, Honeycomb Bread Bakers, or Haven Coffee Roasters, which roasts beans on-site.
Those wanting to sample a variety of local flavors can book an experience with Winter Haven Food Tours, offering various culinary packages that showcase the city’s diverse food scene.
Outdoor Recreation Beyond the Lakes
Beyond water activities, Winter Haven offers numerous opportunities for outdoor recreation. The city maintains beautiful parks, including the Chain of Lakes Park with walking trails, playgrounds, and picnic areas. Aviation enthusiasts can visit Jack Brown’s Seaplane Base, one of the oldest continuously operating seaplane bases globally, offering scenic flights and lessons.
Nature lovers should visit the Street Audubon Center for bird-watching and educational programs about local ecosystems. For those seeking fresh produce and local crafts, the Winter Haven Farmers Market operates every Saturday, showcasing the region’s agricultural bounty.
With its perfect combination of natural beauty, family attractions, cultural venues, and small-town charm, Winter Haven truly lives up to its name as a haven in Central Florida – a destination worth exploring for both residents and visitors alike.
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POI #1 – Dino’s Drive-In, 2929 Havendale Blvd NW, Winter Haven, FL 33881
POI #2 – The Outpost RV Resort Park Community, 2250 US-92, Winter Haven, FL 33881