Winter Haven: Recreation, Culture and Water Sports

Winter Haven combines major theme parks with trails, water sports and cultural offerings. The options range from LEGOLAND® Florida Resort and Peppa Pig Theme Park to theater, historic memorial sites and activities on the Chain of Lakes. When deciding on Winter Haven, you can weigh whether theme parks, outdoor activities, water or a cultural program should be the focus of your trip.

Theme Parks and History

LEGOLAND® Florida Resort spans more than 150 acres and offers over 50 attractions. The park opened on October 15, 2011, on the historic grounds of Cypress Gardens in Winter Haven. This connection between the theme park and local history gives your visit a special connection to the area.

Peppa Pig Theme Park is just a few steps from LEGOLAND Florida Resort. Its offerings include several rides, interactive attractions, themed play areas and water play zones, as well as live shows every day. This lets you include both parks in your trip planning based on their different attractions. Attractions, operations and showtimes may change; check the current schedule before your visit.

Trails and Outdoor Activities

Winter Haven has more than 13 miles of trails. The 3.6-mile Chain of Lakes Trail forms the backbone of the trail network. These figures offer a concrete comparison between the length of this individual trail and the total extent of trails in the city. When planning your time outdoors, you can choose between a route with a specified length and a larger network.

The Winter Haven Skate Park offers another way to get active. The 17,500-square-foot facility includes a large flow bowl and a long, linear street course. The course follows the natural contours of the land and offers a view over Lake Silver. The combination of the bowl and street course defines the character of the facility, making it quite different from a walk on the city’s trails.

Water Sports on the Lakes

You can add a range of water-based activities to your plans on the Chain of Lakes. The Living Water Boat Cruises offers sightseeing cruises on Winter Haven’s lakes. Paddleboard Winter Haven offers lessons, tours and races there. These options appeal to different interests: a cruise, a paddleboard lesson or a race are different ways to enjoy the water. Tour formats and booking options may change, so check the specific offerings in advance.

Water skiing is also part of the program at Lake Silver. The Cypress Gardens Water Ski Team puts on shows there every month. Check the dates before planning, as schedules and venues may change. The World Barefoot Center teaches barefoot water skiing to people of all ages and skill levels. So, in addition to watching, you can also consider lessons in this distinctive water sport.

History, Theater and Music

The Museum of Winter Haven History is located in the Woman’s Club building. The building was added to the U.S. National Register of Historic Places in 1998. At the museum, you can see memorabilia, photographs, films and objects directly related to Winter Haven’s history. Gram Parsons Derry Down also combines a present-day cultural purpose with a historical connection: the fully restored venue offers musicians of all ages and skill levels a place to meet and make music together. On November 5, 2015, Gram Parsons Derry Down received a historic marker from the Florida Department of Historic Resources.

There are several different options for theater enthusiasts. Polk State Theatre stages its main productions at the 485-seat Winter Haven Fine Arts Theatre. Polk State Theatre students present an annual program featuring works ranging from classical comedies and musicals to Shakespearean dramas. Theatre Winter Haven’s season runs from September 1 to August 31. If you’re planning a theater visit, check the schedule for your travel dates. Historic Ritz Theater is another entertainment venue in Winter Haven.

Culinary Tour

Winter Haven Food Tours offers a 2.5-hour culinary experience that includes historic sites and venues in Winter Haven. During the tour, guests sample themed local cuisine described as five-star cuisine. Participating venues and menus may change; check the tour details and specific tastings in advance.

Discover more destinations: Lake Wales, Lakeland, Bartow, Haines City, Fort Meade, Davenport, Cypress Gardens, Polk City

For the main travel overview: Polk.