In 1849, Dr. John Westcott completed an extensive survey of the area, including mapping many of the local lakes.

[3] By the end of the century, the population grew to approximately 400 and on June 22, 1911, the City of Winter Haven was officially incorporated as a town.

[12][13][14] During the 1930s and 1940s, citrus magnate, John A. Snively operated one of the largest fruit packing plants in the world in Winter Haven.

Many famous celebrities of that time visited the park, including Elvis Presley, Frank Sinatra, Betty Grable, and King Hussein of Jordan.

On January 21, 2010, the site of Cypress Gardens was formally announced as the selected location for the Legoland Florida theme park,[16] which opened on October 15, 2011.

[17] Winter Haven features many buildings designed by the architect Gene Leedy, one of the founders of the Sarasota School of Architecture.

In February 2012, the Orange Dome was demolished to make way for The Landings, a proposed $150 million mixed-use development that was intended to include high-end retail stores, restaurants, hotels, apartments and a new movie theater to be built at the Chain of Lakes Complex.

[20][needs update] Pughsville was a neighborhood of Winter Haven where African Americans built a community after the Civil War.

[21] According to the marker, Pughsville was one of Winter Haven's earliest neighborhoods and was settled by African Americans who cleared the land in the southwest section of the city.

Pughsville was named for an early black pioneer, Reverend Charles Pugh, who was a founder of Zion Hill Missionary Baptist Church.

The community was most active from the 1900s until the 1950s and had an African-American school, social halls, small grocery stores, and restaurants where some residents worked.

Pughsville produced Winter Haven's first African-American commissioner and mayor Lemuel Geathers, medical doctor, fire fighter and postal worker.

Winter Haven is located within the Central Florida Highlands area of the Atlantic coastal plain with a terrain consisting of flatland interspersed with gently rolling hills.

[27] In 2011, after six years of construction and political infighting, Winter Haven opened a canal lock system connecting the two chains.

[26] The lakes in Winter Haven teem with life, including alligators, bald eagles, great blue herons, and more.

[24] Winter Haven is located in the humid subtropical zone (Köppen climate classification: Cfa).

The months of June, July, August, and September, which includes the height of the Atlantic hurricane season, are by far the rainiest time of the year.

Four-time NBA all-star and Olympic gold medalist guard, Otis Birdsong, also grew up in Winter Haven.

Winter Haven has many successful sports programs, both recreational and competitive, serving the youth in the community.

His son, Dick Pope Jr. popularized barefoot water skiing, bringing early pioneers such as Don Thomson to Cypress gardens to develop novel acts such as tumble turns, backwards barefooting, front to back and beach starts to please the theme park crowds.

"Banana George" Blair, who still holds several water ski world records, was first introduced to the sport while visiting Winter Haven in the 1950s.

Winter Haven was a Major League Baseball Spring Training site for many years, first at Denison Field and later at Chain of Lakes Park.

The stadium was rebuilt in 1947 with a larger grandstand and in use today for college and high school football, soccer, track and field, and other events.

The Red Sox played in the newly built Chain of Lakes Park, a state of the art facility at that time.

When the Red Sox left to Fort Myers, Florida in 1992, the city of Winter Haven sought a new Major League Baseball team.

In December 2020, Winter Haven and Polk County agreed to demolish the stadium and replace it with baseball diamonds and general-purpose athletic fields.

In 2008, News Chief was taken over by the Lakeland Ledger and operations were merged into that paper's Winter Haven branch.

Local commuter bus service is provided by Winter Haven Area Transit[46] and the Citrus Connection.

[47] Winter Haven's Gilbert Airport and the adjacent Jack Browns Seaplane Base are located 3 miles (4.8 km) northwest of the central business district.