By Steve Flairty
NKyTribune columnist
One could rightly say that Bill Penn “lives in the past” if you take a quick look at his writings, most all regarding Kentucky history, and particularly about the heritage of Harrison County and the Woodford County area around Midway.
His interest in such should not be too surprising, as Bill and his wife, Leslie, are the proprietors of the popular Historic Midway Gift Store, a popular mainstay in downtown Midway since 1996. The store offers a wide assortment of items to customers, including books, jewelry, and souvenir items.
His passion for local history started as a young person growing up in Cynthiana, where he would graduate from Cynthiana High in 1962. “I hung out at the library a lot,” said Bill. Much of his reading material dealt with the Civil War, and especially its connections locally. “They had Basil Duke’s History of Morgan’s Cavalry, and they had some books written in the 1880s. One was called Campfires of the Confederacy.”
Campfires, Bill noted, introduced him to a picture of the Confederate flag, which he considered to be artistically attractive, though he was not especially attuned, at that time, to the societal connotations of the flag. “The issue of slavery was something we all didn’t realize happened, probably,” he said. “Morgan (John Hunt Morgan) was dashing. We knew he came across the covered bridge, and we had pictures of that. The flag was pretty . . . we even had made a clubhouse, a few of us kids, with sheets of plywood and had a Confederate flag over it. I still have it (the flag).”
By high school age, Bill acknowledged that there was more to the Civil War than the Morgan connection to Cynthiana. Later encouraged by teachers at the University of Kentucky where he majored in accounting and took several history elective courses, Bill kept up his expanded research passion for the Civil War while entering a thirty-three-year career as an accountant. Meeting his future wife in Decatur, Illinois, where his duties took him from Kentucky for eighteen of those years, the married couple moved back to his native state, settling in Midway in 1985.
By 1995, he released Rattling Spurs and Broad-brimmed Hats: The Civil War in Cynthiana and Harrison, Kentucky (self-published). The book started as a term paper he did in famed Kentucky historian, Dr. Thomas Clark’s, class at the University of Kentucky. In 2016, University Press of Kentucky published his follow-up book, Kentucky Rebel Town: The Civil War Battles of Cynthiana and Harrison County, based greatly on research from his first book.
Of Kentucky Rebel Town, Kentucky historian Berry Craig called Bill’s work “likely the most detailed account of Harrison County in the Civil War ever written.” Similarly, Civil War expert Kent Masterson Brown noted that Bill’s “treatment of two great battles of Cynthiana are, without question, the best ever done. Not only does Penn clearly describe the troop movements in great detail—he also provides a glimpse of the appearance of the combatants on both sides, as well as the equipment and weapons they used.”
He shies away from formulating summary reflections about the Civil War, saying that he mainly just “enjoys researching the subject.” He did offer a comment when I asked about Cynthiana’s overall importance to the war in general. “Morgan was the most well-known Confederate in Kentucky,” he said. “On two of Morgan’s Kentucky raids, the most significant battles were at Cynthiana.” That said, Bill certainly also knows “where the bodies are buried” in the local Battle Grove Cemetery and recently discovered that the Penn genealogy shows several members who fought in the war. To the old-timers around town, information like that brings a sense of, at least, some wonder. It seems that Bill Penn, in sharing what he finds, is a big part in creating the wonderment.
At age 80, his love of discovering by poring over many pages of material for many hours is what he, with a grin, calls his “research rapture.” Much of it he does at the Kentucky Heritage Council, in Frankfort, along with libraries and at home, online. Since 2000, he has edited the Harrison Heritage News, a newsletter from the Harrison County Historical Society. In recent years, he’s created short, but carefully cited books that demonstrate his love of local history and genealogy:
• Midway History Timeline (2008)
• Civil War in Midway, Kentucky (2008)
• Lost Buildings of Harrison County, Kentucky (2022)
• Henry Lewis Martin (profile of a Woodford Countian who owned his own “Calumet Farm” before the celebrated one at Keeneland)
• History of Harrison County Rural Electric Cooperative, 1938-2001 (in-process; his father was manager of the cooperative for 30 years)
There are other subjects that Bill likes to research, too. They include the early Kentucky frontier surveyors (even pre-Daniel Boone era), studying outlaws such as Jesse James and Billy the Kid, along with having an interest in antique guns. He also plans to do further research on the nearby Offutt-Cole Tavern (should be appropriately titled ‘Lee-Cole’ Tavern, he maintains), which he mentions in the Midway History Timeline. I wouldn’t be surprised if his list continues to grow as his research rapture mentality continues to invigorate him.
Bill and Leslie have demonstrated their musical talents at various venues around the central Kentucky area. Leslie is a flutist, and Bill has played stringed instruments such as the fiddle, guitar, mandolin, and a five-string banjo. He’s played since he was in his 20s, and recently took piano lessons.
The couple’s presentations have been severely curtailed lately, however, because recently he had several fingers on the left hand amputated because of an autoimmune condition. Despite his injury, Bill continues to play the guitar left-handed on a limited basis, a difficult adjustment. Leslie occasionally plays flute at the Midway Presbyterian Church. Unquestionably, both are talented and have shown themselves as positive community forces.
Bill loves Midway, but for the subject of his research, he maintains that his “heart is in Cynthiana,” where he was reared. Visiting the town these days, he muses about the sights he sees. “I know the history of a whole lot of buildings and families in town. Knowing that, I can appreciate it more. I think people today should study architecture more. A study of history can lead more to preservation.”
Bill Penn shows us that “living in the past” is, in fact, a good thing—preserving our heritage. Maybe we should all do more of it.
What a wonderful story about my old friend, Bill Penn, whose dedication of preserving and presenting Kentucky history has been a source of pride to all of us that grew up with him in Cynthiana. Congrats Bill on this well deserved recognition of you and your work.
Yep, steady Bill…one of the many good people I’ve known from Cynthiana.