The Plainview (Texas) Daily Herald posted a fascinating story about the obelisks that once dotted the length of the Ozark Trail highway system, which parts of which became early alignments of Route 66.
According to the Drive The Old Spanish Trail Web site (www.drivetheost.com), various trail associations were formed early in the 20th century to encourage local communities to improve and maintain roadways and to aid travelers in finding their way. One of those groups was the Ozark Trail Association which employed a green-and-white paint scheme to mark its path.
Rather than a single roadway, the Ozark Trail had several principal branches and generally followed a line from St. Louis, Mo., to Santa Fe., N.M. […]
At first the group simply painted a green “OT” between two green stripes against a white background on telephone poles, boulders, barns and just about anything that could hold paint.
However, in 1913, organization founder and Arkansas resort owner William Hope “Coin” Harvey suggested erecting “white pillars bearing the inscription ‘Ozark Trails.’ ”
According to the article, only seven such obelisks are known to have survived. One is southwest of Stroud, Okla., on a lonely gravel road that once was the Ozark Trail and, later on, Route 66. The story says the Stroud obelisk had been moved, although that is in dispute.
Miami, Okla., plans on building a replica of the obelisk at Route 66 and Central Street.