(Information taken from historian Sam Steger's research on the festival which appeared in the September 4th, 1996 edition of The Times Leader)
Princeton's first tobacco festival was a five-day event that was staged Sept. 2-6, 1937. This was the most gala event ever to have been staged in the community, and the Princeton Twice-A-Week Leader estimated the crowd reached the 10,000 mark during the opening parade. The festival was kicked off at 2 p.m. on Thursday, Sept. 2, with the parade led by Princeton mayor Dr. W.L. Cash. He was followed by a 1908 Cadillac that was owned by Reg and Sam Ratliff. The Cadillac was followed by the Morganfield High School Band, which was under the direction of former Princetonian, Goodwin Thompson. The band was followed by numerous types of locomtion that varied from other antique autos to tractors, horsemen, horse and buggies, mules, ox carts, bicycles and motorbikes. There were floats from 32 counties from Kentucky and Tennessee that bore 32 queens along with their courts. All the county queens were vying for the crown of queen of the festival. Among the other parade entries were floats from merchants and civic groups. Sara Mohon Sims was the first queen to represent Caldwell County at the Tobacco Festival. She was accompanied by her court: Ann Leech, Denise Keeney and Allison Hearne. The Caldwell County float was aboard a wagon that had been used to haul tobacco and was drawn by a span of gray prize mules. At 4:30 p.m. there was a band concert at the Butler field offered by the Butler High School Band. The next activity occurred at 8 p.m., a baby contest which Robbie Lou Hopgood won. That was followed by a style show.
Friday was merchant's day when special sales were offered and show windows displayed interesting antiques, relics and collectibles. Friday's celebration was kicked off at 10 a.m. with a concert by a black choir, which was followed by a tug-of-war contest at the Butler field. At 11:30 a.m., Jenks Williams, a representative of the Eastern Dark Fired Tobacco Association, addressed the celebrants. Also, a musical group, the Troubadours, roamed through the downtown from store to store spreading song and good cheer. Among the distinguished visitors in town that day were former governor and U.S. Senator A.O. Stanley, Lt. Gov. Keen Johnson and Judge L.K. Wood of Louisville. At 1:30 p.m., the Butler Band presented a concert at Butler field, which was followed by an address from the lieutenant governor. This was followed by representatives from 22 high schools in a tug-of-war contest. An event that was billed as "a goose on a pole," was held that day, as well as potato sack races and a bicycle race on Main Street. The queen of the festival and Miss Columbia were crowned at Butler field at 8 p.m. by Lt. Gov. Johnson. Virginia Winfree of Hopkinsville was crowned queen of the festival, while Sarah Mohon Sims was crowned Miss Columbia. The crowning was followed by the first of four productions of the theatrical pageant "The Black Patch on Parade" at Butler field, which was undoubtedly the largest of any theatricals ever presented in Princeton. The John B. Rogers Tobacco Festival Corp. of New York was commissioned to write the pageant especially for the Princeton affair and it was professionally directed by Howard Edmund Hill. It is stated that this pageant required a stage 200 feet long and a cast of 500 individuals, which compose a large cross section of Princeton. At 10 that evening, the first of three festival balls were staged. The queen's ball was held at the Elks Club.
Saturday was agricultural day and included a horse and mule show at the courthouse. Riding contests and pulling contests with oxen, mules and horses were held at the Butler field. That evening saw another presentation of the theatrical pageant and another ball. The festival continued on Sunday, but allowed time for church worship. A religious musical was held on the Butler field and another presentation of the Black Patch play.
At 10:30 a.m. on Monday, the festival continued with a pet parade for children and a flower show at the Ratliff building. At 1:30 p.m., action moved to the Princeton Ball park for an all-star game that posed a team of all-stars from Princeton and Marion against an all-star team picked from the West Kentucky League. The Butler Band supplied music for this affair. At 4 p.m., festivities moved back to the courthouse square where Golden Glove boxing bouts were staged. Boxers from across the area came. The featured boxer at this event was the holder of the national bantamweight title. The finale of the festival was held in the warehouse of the Eastern Dark Fired Tobacco District, which was located on South Seminary Street. This was the third and last ball and included two divisions - one for square dancing and one for ballroom dancing.
Throughout the festival, there was a tent on the eastern portion of the Butler campus in which merchants displayed wares that varied from radios to shotguns. Also on the Butler campus was a display of farm implements and tools that were utilized as early as 100 years prior and continued on through the years until 1937. No money was spared on that first festival.
The 1938 Tobacco Festival was also a five-day event. It was reported the second year attracted 9,000 people to the parade. The 1939 festival featured a new theatrical pageant, "Smoke Flower," also professionally written and produced, and was once again a five-day event that attracted 18 beauty queens. The 1940 festival was five days, with a beauty pageant but no special theatrical pageant. The 1941 festival also had a beauty pageant but the number of entrants was down. In 1942, it was announced that because of the war effort it was not feasible to attempt to produce the annual Tobacco Festival that year. Therefore, the 1941 festival was the last until the post-war period when it was revived.