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Winchester’s history dates back to the late 18th century, with many individuals coming and going throughout the years. 

During the evening of Tuesday, Feb. 20, residents had an opportunity to learn about one of its earliest and most influential figures. 

To celebrate Black History Month, the Winchester Black History and Heritage Committee, Friends of Holly Rood and the Clark County-Winchester Heritage Commission presented “The Story of Fanny Cole,” telling of the local hero who was also one of Clark County’s earliest businesswoman, at the Governor James A. Clark Mansion – also known as Holly Rood – at 28 Beckner Street. 

“The things that she accomplished during the Antebellum [South] were phenomenal,” said Jane Burnam, a former Clark County elementary school teacher who portrayed Fanny Cole in a live presentation telling of her life story. 

Historically speaking, the Antebellum South is considered the time period from the end of the War of 1812 to the beginning of the Civil War in 1861. 

Cole, born in the early 1770s into slavery in Virginia, came to Kentucky in the 1820s as the property of John Battaile. 

Shortly after, Cole – already in her 50s – met and married Aaron Cole, a free man by that time. 

After her husband purchased a home and a lot of land at the present-day corner of Broadway and Maple Street, the two of them kept a grocery store, which continued to be operated by Fanny following Aaron’s death in the early 1830s. 

Becoming a well-known and respected entrepreneur, she also had a small brewery, made ginger cakes, and – following her success operating the store – bought an adjoining lot that featured a blacksmith and wagon makers shop. 

When Cole passed away in 1849, she left an estate valued at approximately $2,260 – nearly $75,000 when adjusted for inflation in 2024 – despite facing the many struggles of African American women of that time. 

On Tuesday, after Clark County-Winchester Heritage Commission President Steve Justice welcomed those in attendance in a room just past the entrance and to the left of the main door, Burnam entered as Fanny Cole singing, “All Day, All Night (Angels Keep Watching Over Me)”. 

During the course of her discussion, she engaged the audience, asking questions such as “What’s Your Worth?” and “What’s Your Value?” 

She also pointed out certain facts, including the act that – at one time – 40% of Clark County’s population were slaves. 

When concluding her presentation, another song – “I Don’t Feel No Ways Tired” by James Cleveland – was sung with many in attendance joining. 

Afterward, refreshments were available for others to enjoy. 

Seeing the large population of those who gathered, including youth, Holly Rood curator Debbie Barnes was enthusiastic. 

“There are so many young people now that are interested in history again,” she said. “I see it more and more. People crave knowing what happened here.” 

Seeing the large population of those who gathered, including youth, Holly Rood curator Debbie Barnes was enthusiastic. 

“There are so many young people now that are interested in history again,” Barnes said. “I see it more and more. People crave knowing what happened here.” 

Barnes added that she hopes others will recall Cole’s legacy. 

“Fanny overcame hardship…she helped people, and she made life better,” she said. “She was just strong, and she was able to accomplish so much.”