By  Mike Miller Updated August 13,  2022

Winter Haven, Florida Things To Do, Lodging, Dining, & Real Estate At End Of Article

Winter Haven is like many other Florida towns: you have to get off the main highway to see the real town. 

Miniland USA at LEGOLAND, Winter HavenMiniland USA at LEGOLAND, Winter Haven
Flickr/Kelly Verdeck

In this case the main Highway is US-17 that meanders across Florida from the Georgia border near Jacksonville to Punta Gorda in Southwest Florida on the Gulf of Mexico.


The town began to develop in the early 1880s in the days before highways when the Plant System built the first railroad across Polk County.

The railroad passed just north of current day Winter Haven.

Vintage Postcard Winter Haven Women's Civic League BuildingVintage Postcard Winter Haven Women's Civic League Building

The town was first called Harris Corners but was incorporated as Winter Haven in 1911.

The canals connecting the chain of lakes were started in 1915, and the town boomed in the 1920s along with many other Florida places.

Downtown Winter Haven, Florida

The 1920s saw many homes built in the colonial revival style, and more than 50 of these homes are on the National Register of Historic Places today.

There are four historic districts in Winter Haven including the downtown area.

The first Publix supermarket was opened in 1930 by George W. Jenkins.

His second store, the first stand-alone Publix, opened in 1935 at 199 West Central Avenue. The building still stands but is no longer used as a grocery store.

First Free Standing Publix Store, Winter Haven, Florida

Learn more about the history of Publix Supermarkets

During the 1930s and 1940s, citrus pioneer John A. Snively operated one of the largest fruit packing plants in the world in Winter Haven.

At its peak, Snively Groves Inc. employed more than 1,500 people. The town is still the center of a major citrus industry.

Mr. Snively was the maternal grandfather of musician Gram Parsons.

The Snively mansion, known as Magnolia Plantation, is now part of the Legoland property and is open for special occasions.

Magnolia Plantation at Legoland

In the years before Walt Disney World opened in 1971, Winter Haven was the destination for more tourists than just about any other place in Florida.

This is because of Cypress Gardens, known as the "Water Ski Capital of the World", that opened in 1936.

Many movies were filmed at Cypress Gardens and thousands enjoyed the Southern Belles and water ski shows until the park finally closed its doors in 2009.

It was reborn under different owners as LEGOLAND in 2011, and the new owners have preserved key elements of the beloved old Cypress Gardens attraction.

Water Ski Show at Cypress Gardens

Winter Haven is the "Chain of Lakes City"

The numerous lakes in this city do not allow a strict north-south and east-west street layout.

The canopied residential streets meander throughout the town around the lakes and offer lots of great scenery.

Many of the lakes have streets around their entire shoreline and these make for great scenic drives.

Several neighborhoods, including the downtown area, have been designated as historic districts and you will see many historic buildings and houses on your drives.

Map of Chain of Lakes, Winter Haven, Courtesy Winter Haven EDC

Winter Haven's nickname - "Chain of Lakes City" - has been earned because of its location among more than 50 lakes ranging in size from tiny to large.

24 of these lakes are connected by canals in the Winter Haven area, making Winter Haven a boater's paradise.

Visitors can rent boats, kayaks, paddle boards, and pontoon boats and spend hours fishing or just enjoying the water.

Spook Hill, Lake Wales, FloridaSpook Hill, Lake Wales, Florida

Winter Haven is also close to many other Florida attractions such as Bok Tower Gardens and Spook Hill in Lake Wales.

Winter Haven has always been a unique Florida town, with or without Cypress Gardens and Legoland.

The town is off the interstate highways in the rolling Central Florida land between Orlando and Tampa. Many tourists miss Winter Haven because it is not on the interstate route.

A scenic Florida back roads travel route is to exit I-4 a few miles west of US-27 and go south on County Road 557 through Lake Alfred. Then catch US-17 and go south all the way to Winter Haven.

The town is about 11 miles south of I-4.  That is far enough to have allowed it to keep its small town charm.

Recommended Winter Haven Restaurant

Harry's Old Place
3751 Cypress Gardens Road
Winter Haven, Florida 33884
Tel: 863-324-0301

Harry's Old Place has been a Winter Haven tradition for almost 25 years. During the winter season you can expect to wait 45 minutes or so to get a table. The wait is worth it because of the quality and taste of the food and the good drinks you can sip while you wait.

Harry specializes in seafood, and the menu changes every day. The modest building sits on the shore of Lake Ned and many of the windows have views of the peaceful water.

There is a small service bar for beer and wine with about three stools just inside the entrance, but plenty of space to wander around on the grounds if you have to wait.

The interior of Harry's is rustic and homey. Nothing is fancy but it gives you a very comfortable feeling.

Harry's Old Place, Winter HavenHarry's Old Place, Winter Haven

Lunch and dinner is served here; the lunch menu is large and varied and the dinner menu even more so. Some unusual items are featured here.

For example, the appetizer menu includes duck fingers, gator bites, baked oysters, escargot in mushroom caps and deviled crab balls. You can get your main entree fried or broiled.

All fried entrees are served with hush puppies and your choice of two: cole slaw, tossed salad, French fries, New Potatoes, rice or fresh vegetables.

Harry's Old Place, Winter HavenHarry's Old Place, Winter Haven

The fried entrees include oysters, grouper fingers, scallops, shrimp, catfish and clams and can be ordered separately or as either a fish and chips special or a combo platter.

Broiled entrees include crab imperial, shrimp kabob, scallops, snow crab legs and Harry's catches of the day. These catches are always fresh and you can have them prepared any way you like.

Landlubbers have not been forgotten with plenty of beef and chicken dishes including filet mignon, garlic steak, New York strip, chopped steak, and plain, Cajun or BBQ grilled chicken breast.

They also serve linguini with clams and shrimp, and pescatore with scallops, shrimp, clams, white fish and mussels on a bed of linguini. Children's dinners include hamburgers, grilled cheese, spaghetti and meatballs and even a peanut butter and jelly sandwich.

The dessert menu is generous, too, and the favorite here is Key Lime Pie.

Harry's Old Place is open for lunch Tuesday through Friday from 1130 to 130, and for dinner Tuesday, Wednesday and Thursday 500 to 900, Friday from 500 to 1000, Saturday 400 to 1000 and Sundays (December 2 through May 13) from 400 to 800.


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