The first oil well drilled in the United States was drilled by John H. Galey in 1859 in Pennsylvania, and with the advent of the gas-powered automobile, the race to find oil began in earnest in the 1920s. In August of 1920, the people of Montgomery County were filled with excitement when news was learned that Preston Oil Company of Columbus, Ohio, would be drilling for oil in the county.
Earlier in that same year, it was determined by prospectors of crude that oil could be found about six miles east of Winona on the Judge McLean Place. Not long after this determination, railroad cars loaded with timber for the derrick and two carloads of casings arrived in Winona. Preston Oil’s representative told the Winona Times that they would be drilling within the month, and according to a report from the state geologist, oil was expected to be found at a depth of approximately 3500 feet. All of Montgomery County was convinced that oil would soon be gushing from the well and would surely mean the dawning of a new Montgomery County.
As drilling began, the entire county was anxious to learn of any news, but none was given by the well owners. As the drill approach 3500 feet in depth, oil excitement began to run high in the county. Speculators began paying as much as $12.50 an acre for mineral rights, and it was even reported that the mineral rights on a 40-acre tract owned by W. J. Herring near the well sold for an amazing $1000 (appx. $15,000 today). At 3400 feet the drill struck “oil sand.” The samples of the sand were reviewed, but while there was a residue of oil, there was none of substance. Undaunted, the Preston Oil Company advised that it would continue drilling until they reached 4000 feet.
As Preston Oil drilled towards 4000 feet, they stopped providing reports of their progress. The silence of Preston Oil caused much rumor in the county. Some rumors began that gas had been struck, but others suggested that Preston Oil had hit hard rock. Still, the people of Winona hoped that the well would be coming in soon. By March of 1921, the rumor mill quietened as town-folk learned that the drilling had stopped, and in June of 1921, the town learned that Preston Oil had stopped drilling at 4500 feet and had abandoned the well. By July of 1921, after almost a year of drilling, the people of Winona were advised by Preston Oil that it had officially abandoned its new well.
As an oil company representative boarded a train leaving Winona, he told the people of Winona not to lose hope because of the abandoned well. He stated that within few years oil “in paying quantities” would be discovered in the Winona vicinity, and oil derricks would be as common in Montgomery County as mules. However, it would be another sixty years before another oil well derrick would appear in Montgomery County. This time the oil well was 14 miles east of Winona on the old Clark Place, but after spending $4 million, Montgomery County’s second oil well, like its first, yielded another dry hole, and its vision of become the next Dallas faded once again.
