For the next ten years Dr. Anna Darrow  would practice medicine, and become a legend.  In 1915 the Darrow’s built the Park Drugs building next door to Raulerson’s Store which had just been completed on South Park Street.  

Dr. Roy ran the pharmacy and did surgery, both human and animal, in the inside office.  Dr. Anna, or “Doc Anna” as she was commonly called, drove all over in her Model T treating patients wherever the need existed.  She charged $1 for an office visit, and $1 a mile for traveling to a patient.  She charged $10 in the beginning to deliver a baby, but changed her fee to $25 later on.  Fishermen, trappers, Indians, and even gangs of desperadoes residing in the area would call on Doc Anna.  No matter the hour or distance she would go.  

The Darrow’s daughter Dolly Darrow had the honor of being the first student in Okeechobee to receive a high school diploma as a member of the class of 1920.  She was the class valedictorian, and there were four graduating seniors in that first class.  In addition to herself, the other graduates were Beryl Lovvorn, Willie DuBose and Alma Camp.  The Darrow family left Okeechobee in 1921 and moved to Stuart. 

The time from 1911 until 1919 was probably the first big “boom” in Okeechobee.  Before this time only a few hardy pioneers were settled on the banks of Taylor Creek.  But the announcement in 1910 of a railroad coming to Okeechobee changed everything for this sleepy little settlement.  

The St. Lucy County Tribune announced in its issue of December 30, 1910 that work would start soon on a branch line of the Florida East Coast Railway running from Maytown in  northeast Florida, down through the Kissimmee River Valley to Lake Okeechobee. 

The official word came from FEC General Manager J. R. Parrott, that Mr. Flagler had given the go ahead to the Kissimmee River Valley Extension.  When Okeechobee City was laid out by FEC Engineers, they named the main north south avenue after J. R. Parrott.  

Primarily responsible for the project was James E. Ingram, a vice president of the railroad, head of Lands  and Development.    Ingram envisioned a great metropolis arising at the southern terminus of his branch line. The name Tantie was deemed inappropriate for this new city, so on October 4, 1911, the post office at Tan tie was officially changed to Okeechobee. Taylor Creek was changed to the Ono-sho-hatchee River but the new name was never popular and was dropped after several years. 

Mr. Flagler stated that the railroad’s purpose was "to develop farmlands, to haul timber and turpentine, to aid the cattle industry and, most important of all, to provide rapid transportation for the catfish industry of the lake."  He hoped to move the FEC repair shops to Okeechobee because it was located half way between Miami and Jacksonville.

In December 1911, officials from the FEC Railway, including J. E. Ingram,  W. L. Bragg, and P. L. Jenkins visited Okeechobee to inspect the area. It was announced that beginning in the new year, Jenkins, a civil engineer, would lay out and survey "the new city of Okeechobee." 

Mr. Bragg would move there and settle permanently in order to sell lots and farm sites. Three land companies, all closed related, were to be involved in the sale of property in the Okeechobee area. The Model Land Company was the land department of the Florida East Coast Railway. The Consolidated Naval Stores Company had a subsidiary known as the Consolidated Land Company and the third was the Okeechobee Company, owned by the Florida East Coast Railway,  whose president was James E.  Ingram. 

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