The town was once a stop on the Northwest Turnpike, one of the main roads west in the early days of the country, running from Winchester, VA to Parkersburg (now West Virginia). Later the town was a stop on the Baltimore and Ohio Railroad that ran between Clarksburg and Parkersburg. During those early 20th century days the city of Pennsboro, WV (population 1,129; all the other communities in Ritchie County are listed as towns) was a thriving place.
If Ritchie County ever had a trademark it was surely the Ritchie County Fair held in Pennsboro. The Ritchie County Agricultural Fair Association incorporated in January of 1887, and promptly leased a tract of land on the outskirts of town from the Bradford family. This was the first Agricultural Fair organized in the state of West Virginia. With the exception of two World War II years (1943-44) the fair was held every year during the last days of August into early September, from 1887 until 1962. By 1922, 20,000 people attended the fair and gate receipts totaled $10,000.
“The Ritchie County fair was certainly one of the grandest fairs in the state when it was in its prime,” says author Rock Wilson. “Vast crowds would gather each year. Horse races were quite prevalent there.”
Racing. First horses, later cars. It’s the second thing the town of Pennsboro is famous for. According to local historian and author Betty Leavengood, the first auto race at what was then called Ritchie County Raceway was held Sept. 1, 1926, featuring 1 horsepower vehicles!
The upgrading of Rt 50 must have been completed as there was a road celebration and 1,000 cars left Pennsboro on September 18, 1927 and traveled east. This procession lasted from 6 am until 6 pm.
Diary of Nancy Clark Dotson (1904 – 1946), p. 46
The rugged Northwest Turnpike had become well paved Route 50 and automobile culture rose to prominence; before too long the railroad pulled up its tracks. Pennsboro, once the beneficiary of a rail connection in an area of under-improved roads, lost its monopoly on accessibility. The raceway began to be replaced by newer tracks in the region and the track’s importance faded.
By 1967, then owners Pete and Ruby Wilson, along with Ideline Hinkel, were feeling the pressure to come up with a plan to attract big-name drivers to the track. To do so they needed a big race, a big purse, and a big weekend. The big race would be a 100-lap Super Late Model feature event. The big purse was set at $1,000 during a time when the Census Bureau pegged the median income per year at $5,974. The big weekend: Labor Day. To attract a large crowd the name had to be just right. Hinkel’s granddaughter coined the name “Hillbilly Hundred.”
In 1976 Carl Short leased the track formally known as Ritchie County Raceway and changed the name to Pennsboro Speedway. He was responsible for attracting the Dirt Track World Championship to the Pennsboro Speedway each October.
According to Allan E. Brown’s “The History of America’s Speedway – Past & Present”, Pennsboro ceased operation in 1987, then operated from 1989 through 1997 and again from 2000 through 2002. The Dirt Track World Championship now makes its new home at KC Raceway in Waverly, OH.
Ritchie County, by Rock S. Wilson, Arcadia Publishing, 2004