During the 1920’s the population of Okeechobee continued to grow.  The County government was now well established, and  the O. O. Davis building served as the county courthouse.  This building was leased from Mr. Davis for fifty dollars a month.   It was located on South Park street and Third Avenue; where Village Square Restaurant is located today.  Construction was the big thing in the 1920’s with the bulk, taking place about the middle of the decade.   Many of the buildings that were constructed during this time are still in active use today. The first Methodist church was built in 1925. 

The County Court House was built in 1926, by the construction firm of Rogers and Duncanson.  John Duncanson was the grandfather of Judge William J. Hendry.  This firm also built during this time the former High School, now the ninth grade center, and the Freedman Building, which was the former Markham Building, now housing Superior Water Works.  During 1925 the County Commissioners found themselves short of money and they started looking for ways to cut expensed on the courthouse, but they finally settled on the original design.  In order to finish the building and furnish it, they transferred funds from a road project and completed the courthouse.  The courthouse was accepted by the county commission February 27, 1927, and occupied in April of that year.  During the early years, 1927-1960’s most of the county offices occupied this courthouse.  Following the 1928 hurricane when this building was less than two years old, it’s hallways were used as a temporary morgue.  The Central and South Florida Flood Control District was organized in front of the Courthouse on October 6, 1947.  There have been at least two graduating classes from Okeechobee High School hold their commencement exercises in the front of this courthouse.  The City Hall was constructed about the same time as the courthouse, using Spanish style architecture so popular in Florida at that time.

Several of the homes along Parrott Avenue were built in the 1920’s those being Ellis and Faith Meserve’s Home, Dr. Wolff Home, Dr. Brown’s Home, (where I grew up, now Berger Real Estate), Judge Durance's Home, and Roy Raulerson’s Home (now the Russell Domer Home).  All of these homes were what was known as “boom time” homes, built in the second half of the decade.  

Okeechobee’s largest building took shape during 1925 and 1926 when the Southland Hotel was constructed on the northeast corner of North Park Street and Parrott Avenue.  For many years this impressive hotel was dominant in the Okeechobee landscape.  J. G. McNeff headed the corporation that built the Southland, but it eventually went bankrupt, and the title passed to the state of Florida due to unpaid taxes. In 1937, Mr. & Mrs. Marshall Conrad “Tom” Pitts purchased the Hotel.  The Southland was three stories high with fifty-seven guestrooms, several storage rooms, and a spacious lobby with fireplace.  There was also a large dining room, a bar, a huge well-equipped kitchen, and a large apartment on the main floor where the Pitts family lived.  The first local radio station WOKC was housed on the top floor in 1962.  My junior and Senior Proms were held in the large dinning room at The Southland Hotel in 1952-53. 

The U. S. Post Office was located in the northwest corner of the Southland Hotel.  Tom Pitts was Postmaster throughout the 1930's and 40's.  The first airmail service from Okeechobee was started in 1938 with The Honorable William (Big Boy) Hendry Mayor and Postmaster Tom Pitts present at the kickoff of this new service.    The post office moved in 1960 after constructing it’s own building, one block east.  Mayor Hendry was the father of  Judge Bill Hendry, of this community.

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