There were several south Georgia families that shared a Ray City – Willacoochee connection.
After 1908, the route of the Georgia & Florida Railroad was from Jacksonville, GA to Madison, FL and provided convenient transportation between Willacoochee and Ray City by way of Nashville, GA, a run of about 34 miles.
- Pleamon Sirmans (1892-1961) was born and raised in Willacoochee, before moving in 1915 to Ray City where he later served as Mayor; buried New Ramah Cemetery, Ray City, GA.
- Francis Arthur Shaw (1866-1933), born and raised at Ray City, later served as mayor of Willacoochee; operated turpentine stills at Willacoochee, Georgia with his brothers, Chester D. Shaw and Lacy Shaw, and brother-in-law, William Clements; buried Willacoochee City Cemetery, Willacoochee, GA.
- The Harper family for a while called Willacoochee home; Wilma Harper (1909-2002) would later teach at the Ray City School.
- William Jackson Cook (1867-1951) and Annie Laura Mathis (1871-1910) in the early 1900s left the Watson Grade community near Ray City for Willacoochee where Mr. Cook worked as a sawmill supervisor; buried Empire Cemetery, Lanier County, GA
- Gideon D. Gaskins (1859-1916) was born and raised at Ray City; moved to Willacoochee about 1887 where he was a store owner and innkeeper; wife Lula Clements later returned to Ray City; buried Willacoochee City Cemetery, Willacoochee, GA.
- Thomas R. Cox (1887-1957), born and raised at Ray City, GA; became bookkeeper for the Bank of Willacoochee; later returned to Ray City; buried Beaver Dam Cemetery, Ray City, GA.
- Skidderman Henry Howard Thompson (1898-1982) and Rose Lee Drawdy Thompson (1900-1986), of Ray City, would make their home in Willacoochee in the 1920s.
- Cauley Shaw (1883-1961), who was the Ray City Police Chief in 1914, kept the law in Willacoochee in the 1920s.
- Dr. Bailey Fraser Julian, Jr. (1865-1907) made his practice as one of the Medical Men of Ray’s Mill (now Ray City) for a brief period in the late 1890s; Dr. Julian later served as railway surgeon on the Brunswick & Western RR which ran through Willacoochee.
- Rebecca J. Fox, an evangelist whose revival tent was burned at Ray City in 1909 held a revival at Willacoochee; her future husband, Manassah Henderson of Ray City, was a member of the Missionary Baptist Church at Willacoochee.
- Sankey Booth who was superintendent of the Willacoochee school in the early 1920s headed up the Ray City School in 1924.
- Wayne Putnal was a barber in Willacoochee in the 1920s, before opening a barbershop in Ray City.
- Jesse Bostick and Sarah Ann Knight, of the Rays Mill area, had been among the early settlers at Willacoochee.
Ray City History Blog 
Bryan Shaw said,
April 23, 2016 at 7:21 am
Arthur Shaw, of Willacoochee, was also business partners in the turpentine operations with his brothers, Chester and Lacy Shaw. Lacy operated the commissary at the still. He later ended his partnership with Arthur and farmed near his parents home place in Lois just off Possum Branch Road. About 1917 he sold his home to Pleamon Sirmans and moved into Ray City and operated a hardware store there before moving to Valdosta about 1927 or so.
The location of the turpentine operation was actually about a mile or so south of Springhead Methodist Church in Atkinson County. The terminus of the Pinebloom railroad which ran through Willacoochee was at Shaws Still which is shown on the early 1900 railroad maps. The intent at one time was for the Pinebloom to terminus at DuPont, however the extension was determined to be financially unsound and it was given up. Very little is visable of the old Pinebloom railroad bed between Willacoochee and Shaws Still. The terminus of the railroad was about where the Henderson Lumber Company had its operation, near today’s Henderson Road and Springhead Church Road. The still site is no longer visable and is on a private hunting preserve now.
—Bryan Shaw
The OP&V, originally called the Fitzgerald, Pinebloom & Valdosta, was a logging road and occasional common carrier owned by the Gray Lumber Company. The 52-mile Lax-Pinebloom-Nashville line was completed in 1901-03.
In 1906, the OP&V sold the section south of Pinebloom to the Douglas, Augusta, & Gulf Railway (which was controlled by the Georgia & Florida). It continued to operate the tracks north of Pinebloom. (Pinebloom was a flag station on the Atlantic Coast Line Railroad a mile east of Willacoochee with a 1896 population of about 200. The Gray Brothers saw mill was its largest enterprise.)
The line was renamed the Ocilla, Pinebloom & Valdosta Railroad in 1910, and in 1915 the Henderson Lumber Company gained control.
The 1918 Report of the Georgia Railroad Commission listed the OP&V as a 27-mile line between Gladys, a point on the Ocilla Southern Railroad, and Shaw’s Still, which was about nine miles southeast of Willacoochee. Two years later the Commission indicated that the OP&V had been dismantled and listed its successor road, the Willacoochee & DuPont, as a 9.5-mile line between Willacoochee and Shaws Still.
In 1915, when the Henderson Lumber Company acquired the Ocilla, Pinebloom, & Valdosta Railway, it ran from Gladys to Shaw’s Still. In 1918, the Willacoochee & DuPont Railroad purchased the line and reportedly abandoned the tracks between Gladys and Willacoochee the following year (or used them only for logging or hauling naval stores and turpentine). It continued to operate the eastern and southern section of track from Willacoochee to Shaws Still, but apparently was not able to extend the line past Shaws Still to DuPont, a town on the Atlantic Coast Line in Clinch County. In 1922, this track too was abandoned.
Source: http://www.RailGa.com