The Owensboro historical marker reads:

Once the intersection of two competing railroads, the South Florida Railroad (part of the plant System, later Atlantic Coast Line Railroad, built in 1884-85) and the Florida Railway & Navigation Company (later the Florida Central & Peninsular Railway and eventually Seaboard Air Line Railway) crossed here in 1887. A school existed here, as did a post office from 1886 to 18899 and 1902 to 1906.

Lutz Brothers Shingle Mill was located nearby, ca. l1895. With the discovery of clay deposits, a brickyard and kiln began operating about 1907, making bricks which sold at six dollars per thousand. Mickler & McLeod quarried rock and crushed limestone in the 1920s.

Until the advent of modern railroad technology, a two-story frame switching station was located at the intersection of the two railroads. An overpass was built over the switching station and rails in 1948-49 when the federal highway was re-aligned. Atlantic Coast Line Railroad and Seaboard Air Line Railway merged in 1967 to become Seaboard Coast Line Railroad (now CSX Transportation) and removed the Atlantic Coast Line tracks in the late 1980s, resulting in the demolition of the overpass.

In 1989 the State of Florida acquired the former rail right-of-way and developed the Withlacoochee State Trail as a linear recreational greenway. Owensboro became its southern terminus.

The Owensboro post office was established on April 14, 1886. (It was discontinued in 1899, re-established in 1902 and discontinued in 1906. Postmasters were: Frederick L. Bridge, Robert J. McCutcheon, Charles H. Lutz, John G. Dellinger, William E. Brown, and Annie Keith.)

An 1885-86 list of Hernando County schools shows an Owensboro School.

Minutes of the Hernando County school board of Oct. 4, 1886, show that the Owensboro school was opened with Mrs. Clara Bohner as teacher.

McCormick has: John O’Berry in Orange House and O’Berry Lake 1893 - 1914.

School board minutes of Sept. 5, 1887, show the O’Berry School, No. 11, post office Owensboro. Trustees were: J. W. O’Berry, H. C. McRae, Thos. Blitch.

School board minutes of Dec. 5, 1887, have: “The Supt. read the reports of his visits to various schools and called particular attention to the fact that the school house at Owensboro No. 11 was found to be about 40 feet south of the land donated to the school board. It was moved and carried that the Supt. investigate this matter and report at the next regular meeting of the Board.” School board minutes of Jan. 2, 1888, have: “The matter of the location of the school house at Owensboro was discussed and action postponed indefinitely.”

On April 11, 1889, Owensboro received one vote in the election to choose the permanent county seat of Pasco County.

Miss Jessie Roberts was appointed the teacher at the Owensboro school for the 1895-96 term.

J. G. Dellinger was appointed the Owensboro teacher for the 1897-98 term.

School board minutes of March 5, 1900, have: “The Trustees of Wake Forrest Academy reported that they had sold the Owensboro School lot to J. W. O’Berry for the benefit of their school, and asked the Board to execute a deed. On motion the chairman was directed to convey the said lot to J. W. O’Berry.”

Around 1907 a brick yard was opened at Owensboro, but the business was not successful.

The Cummer Co. is said to have originally intended to build its lumber mill at Owensboro but did not because of World War I. The mill was later built at Lacoochee.

On Oct. 12, 1923, the Dade City Banner reported that a freight train on the Seaboard Air Line was wrecked at the crossing of the Atlantic Coast Line railroad at Owensboro early Thursday morning.

On Oct. 21, 1949, at 1:15 a.m. a Seaboard train crashed into an Atlantic Coast Line train at Owensboro. The wreck also caused damage to the new highway overpass that had been completed earlier in the year.

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