Sunrise over Lake Howard · photo Floodmfx, CC BY-SA 4.0A Winter Haven Guide
Things to do in Winter Haven.
Winter Haven sits on a chain of canal-linked lakes halfway between Orlando and Tampa, with LEGOLAND Florida at its edge and a walkable brick downtown at its center. This guide covers mornings on the water, the Saturday market, the lakeside trails, and the day trips nearby.
Start with the water.
Winter Haven is built around the Chain of Lakes, and its lakes are joined by navigable canals. You can boat from one lake to the next without ever loading a trailer. The chain is also serious fishing water, with a bass fishery that the state wildlife commission (opens in a new tab) tracks and anglers travel for.
You do not need a boat of your own: the outfitters listed here rent kayaks and pontoons, teach paddleboarding, and run guided cruises.
- Off The Chain Kayak CompanyKayak rentals, delivered to the lake you pick
- Paddleboard Winter HavenLessons and tours, most from Lake Summit
- Central Florida WatersportsPontoon rentals and sunset cruises, southern chain
- The Living Water Boat CruisesGuided wildlife and history tours of the chain
A theme park with roots.
Before LEGOLAND there was Cypress Gardens, which opened on the shore of Lake Eloise in 1936 as Florida's first commercial theme park. LEGOLAND Florida Resort took over the site in 2011 and kept the oldest part of it intact: the historic botanical gardens (opens in a new tab) still stand inside the park, included with admission.
The rides run small in scale, and the park includes a water park on the property with the Peppa Pig Theme Park next door. From The Jade it is about a 10 minute drive, close enough that an afternoon there does not require planning a whole day around it. Distances and travel times are approximate, under typical conditions.
Central Avenue and around
Downtown keeps a calendar.
Downtown is a few walkable brick blocks around Central Park. Grove Roots brews on site, Union Taproom pours across the street from the park, and the Ritz Theatre has been putting on shows downtown for about a century. Theatre Winter Haven produces a full season of its own on top of it. Main Street Winter Haven (opens in a new tab) runs the standing calendar.
The walk from The Jade takes about 15 minutes. The neighborhood page has more on downtown, and the one and two bedroom floor plans show the homes at The Jade. Rent and fees for every home are set out on What You’ll Pay. Distances and travel times are approximate, under typical conditions.
- Saturday farmers marketMagnolia Avenue, every Saturday morning
- First FridayDowntown, the first Friday evening of each month
- OktoberfestCentral Park, each fall
- Holidays on CentralCentral Park, each December
The lakes, on foot.
The city maintains more than thirteen miles of trails (opens in a new tab), and most of the good walking follows the water. South Lake Howard Nature Park has paved loops and about a thousand feet of boardwalk along Lake Howard, where you may see herons or an alligator. The Chain of Lakes Trail is the main trail, and Lake Hartridge Nature Park has a shorter loop for an easy evening walk.
Golfers have Willowbrook, the city’s own eighteen-hole course on the north side, where the wildlife watching is nearly as good as the golf.
Worth the drive.
Bok Tower Gardens, near Lake Wales about half an hour south, has a singing carillon tower above hilltop gardens.
- Lakeland25 min drive
Frank Lloyd Wright's largest single-site collection, at Florida Southern College
- Orlando55–65 min drive
The theme park capital, for the days you want it
- Tampa~60 min drive
The Gulf coast, Ybor City, and the bay
Distances and travel times are approximate, under typical conditions.
