Following the Civil War, ratification of the 13th Amendment in December 1865 abolished slavery in the United States. Free blacks would experience difficult times in post-war Clark County. The majority of men worked for wages as farm laborers, the women in domestic service, and most families lived in extreme poverty.
Comparing the 1860 and 1870 censuses we find that one in four blacks left the county after the war, likely hoping for better prospects in the North. Enterprising individuals and those with a skilled trade fared better than others, and a few were able to acquire property in one of the black communities that sprang up in Clark County: Lisletown, Hootentown, and Dry Ridge. Housing for African Americans in Winchester was limited to an area centering on North Highland and East Broadway, as well as a small portion of East Hickman Street (later expanded to become Kohlhassville). These opportunities greatly expanded with the creation of Poynterville.
The man who gave the community its name, Wiley Taul Poynter (1838−1896), was born in Montgomery County, grew up near Frankfort, and came to Winchester at a young age. At 17 he was the principal and a teacher at the Winchester Academy. He served with the Union Army during the Civil War as a regimental quartermaster for the 16th Kentucky Infantry.
Returning to Winchester, Poynter, an ardent Methodist, entered the ministry. He pastored a church in Winchester for four years, then in 1879 he purchased the Science Hill Female College in Shelbyville—the famous school established in 1825 by Clark County native Julia Ann Tevis. The buildings are now occupied by the Wakefield-Scearce Galleries.
Bringing our story back to Winchester, we find that Poynter purchased 65 acres of land adjoining the west side of Winchester from William H. Winn. In July 1867 Poynter had the tract laid out in 52 lots and platted as “Poynterville.” The tract was bordered on the north by Walnut Street, on the east by First Street, on the south by an extension of Washington Street, and on the west by Elm Street, which was then called “the old Paris Road.” This new suburb became the first of many in Winchester’s history.
It seems Reverend Poynter intended his suburb to become a community for black families. This notion is supported by his article, “The Church and the Black Man,” published in the Methodist Review. The article begins, “I risk nothing in saying that among the imperative and pressing duties of the American Church, and especially of the Church in the Southern States, none is more important than the duty to the colored people in our midst”... and that first they “must be housed in homes of their own. There can be no true progress without this.”
Wiley Poynter put his words into action. From July 1867 through the end of the year he sold 19 lots, all to African Americans. He continued the practice after leaving Winchester. Between 1867 and 1890, he made 54 deeds conferring 66 lots in Poynterville. All the sales but one were to African American men or women whose names are shown in the table. The lots sold exceeded the number laid out in the plat as some of the sales were for “half lots.” Poynter also sold lots on credit—an unusual practice for selling to freedmen at that time.
Few of the purchasers of lots in Poynterville had an occupation other than farm laborer. John Allen was a house painter, Mason Fry a distillery worker, Jerry Stephenson a grocer, George Miller a butcher, Aaron Taylor a post-and-railer (fence builder), Gibson “Gip” Taylor a railroad worker, Samuel Brown (husband of Margaret) a harness maker, and Thomas Webb a blacksmith. Laborers who purchased lots must have carefully saved their wages.
At least four of the buyers—Mason Fry, Reuben Ragland, Joseph Price, Burgess Ramsey—were Civil War veterans who could have used their military pay to buy lots. John Allen, Reuben Ragland, and Shelton Jones were trustees of the ME Church of Winchester (on Broadway at Church Alley). Thirteen of the buyers were women; their reported occupations were housekeeping and domestic service.
Eliza Burch purchased a lot in 1869. She died in 1876. She willed her house and lot in Poynterville to her son Samuel, who “has for the last four years cared for me during my sickness.” It was to be “compensation for his kind treatment of me and his loving care and protection.” She could leave sons Philip and Ames only “a mother’s affection.” She added, “My other children were sold during slavery, and I do not now know whether they are still living or not. I can only leave for them a mother’s prayer that they meet me in heaven.”
One year after Poynterville was laid out, the heirs of John Bruner, Winchester’s first tanner, established an adjoining suburb called Brunerville. Brunerville lay on the west side of Elm Street and was framed by Walnut, Upper, and Washington. Brunerville persisted until sometime in the 20th century, after which time the area was assumed to be part of Poynterville.
The Kentucky African American Encyclopedia has an entry for “Bucktown,” which states that it is officially a part of Poynterville. The origin of the name is uncertain. Some credit it to Buck Clay, a sometime grocer who resided on Upper Street. Locally, Bucktown is most closely associated with the area of West Washington Street that was once the center of black businesses in Winchester. The area was recognized in 2008 with the dedication of Heritage Park at the corner of Washington and Maple Streets.