The Roaring Twenties and the Florida Boom...
- Bob Gernert
- Apr 1
- 5 min read
As Winter Haven entered the1920s the U.S. Census listed the population at 1597 people - a small but motivated populace that had embarked on big projects like connecting the areas lakes by canals. Armed with “can do” optimism, they welcomed the “roaring twenties” with gusto.

NEW CITY HALL: In 1920, a bond issue was approved to build a new City Hall on the SW corner of Sixth St. and Central Ave, SW. It would literally replace a substandard corrugated structure that had served that purpose on the site. The building was a bold statement for the fledgling community and housed both the Police and Fire Departments on the first floor, with rooms for the city administration, Chamber of Commerce, a courtroom and jail on the upper level. It would open in 1923.
HAVEN HOTEL: The year was 1921 and Winter Haven residents R. H. Ross and J. Walker Pope (father of Cypress Gardens founder Richard “Dick” Pope) decided the city needed a good hotel. They sold stock to local residents and construction was soon started. However, it only got as far as the iron framework “skeleton” before the project ran short on funds. To resume work, bonds were sold to raise the needed funds and construction soon resumed.
By late October 1924 the hotel was what the Florida Chief (forerunner of the News Chief) called “one of the most magnificent in the country,” The Haven Hotel was ready to open and a sunny late October day found 350 of Winter Haven’s then 1600 residents gathered to celebrate the opening of the six-story coquina shell building overlooking Lake Howard.
CHAMBER OF COMMERCE: In September of 1923 the Board of Trade transitioned to become the Winter Haven Chamber of Commerce with offices in the new City Hall.
CITY COMMISSION: On January 1, 1924, the village implemented a City Commission/City Manager form of government having outgrown the town council format. Originally there were three commissioners, and today there are five.

THE ORANGE FESTIVAL IS BORN: A significant agricultural celebration was born in 1924 as the Polk County Orange Festival. The Orange Festival was the brainchild of Dr. R. A. Nichols, pastor of the Christian Church in Winter Haven. He had been a lecturer for several years on the Chautauqua Circuit (a traveling tent show in the early 1900s that brought cultural programs such as lectures, music and plays to remote areas of the country). He had witnessed the crowds that were attracted to many county fairs and was reminded of their popularity when he happened across an article about the Portland, Oregon Rose Show. Dr. Nichols took his idea to the Winter Haven Chamber of Commerce that at the time had a considerable membership for a town of 2,000 people. The Chamber immediately embraced the concept and four months later the first Orange Festival was held on January 22, 23 and 24, 1924.
The Festival would grow to become the Florida Orange Festival, later the Florida Citrus Exposition and finally the Florida Citrus Showcase. From humble beginnings in 1924, the festival brought millions of people to Winter Haven to celebrate citrus with fresh fruit displays, popular television and radio shows, and spectacular midways.
But as the industry moved away from fresh fruit, major theme parks opened and disease ravaged what was left of our once proud groves, the festival folded in 2008.
THE BANKER’S CUP AWARD: The Banker’s Cup Award is considered our community’s highest honor. The first award in 1923 was sponsored by the Winter Haven Clearing House Association (serving the three local banks at the time) and presented at the last annual meeting of the Board of Trade. The tradition continued with the exception of war years 1943-45 (and more recently 2020 due to Covid) honoring one individual each year. In 1965 the award was expanded to honor both a man and woman annually. From 1923 through 1996, a person was required to win the honor three times to take permanent possession of the large loving cup, with most receiving a smaller token cup as a permanent memento at the end of their year. In 1997, the award committee changed the process and now permanently awards the cup to each year’s recipients. The 2024 recipients are Jane McGinnis and T. Michael Stavres.

THE BOOM BEGINS: Many factors contributed to Florida’s land boom of the 1920s but none more than World War I. During the war, wealthy U.S. families could not travel to such places as the French Riviera and had to find alternate tourism destinations. The east coast railroad had been completed to the Miami area and the tropical landscape, ocean beaches and breeze opened the door to what would become Miami’s primary economic engine at the time — tourism. The influx of tourists and money created excitement, optimism, and land sales. Construction of homes and accommodations grew to a fever pitch, and a gridlock of building supplies developed among the railways. The blockage was so acute that the railroads declared a moratorium on construction freight and only allowed essential shipments such as food and medical supplies. Ironically, an accidental sinking of a ship in the mouth of Miami’s harbor prevented the last viable delivery point from accepting construction materials. That fact, plus the Hurricane of 1926, coupled with poor construction standards, meant that by the end of that year, the boom was a bust.
Real estate values in Florida evaporated, and many individuals, companies, and municipalities defaulted on loans and bonds. Winter Haven would be among them. This would foreshadow the Great Depression.

WILLIAMSON/RITZ THEATER: January 28, 1925, the Williamson (now The Ritz) Theater opened to great fanfare. Originally equipped for silent movies and Vaudeville, the theater transitioned to “talkies” and was renamed the “Ritz” in 1932.
POSTSCRIPT
Of note during a tumultuous decade is the founding of the Winter Haven Rotary Club, which celebrates its centennial in 2025. And in 2027 the Garden Club of Winter Haven will mark its 100th Anniversary. Both plan special commemorations.
Next Month: The 1930s: Winter Haven Defies the Great Depression