Communities
In 1860, before the Civil War, Winchester’s 48 free Blacks lived in 15 households widely scattered throughout the downtown area. Following Emancipation, newly freed families were pressed to find employment and housing. The majority worked in the service industry in town and farm labor in the county, and began to find housing in segregated communities.
The first African-American neighborhood developed in the North Highland-East Broadway-Church Alley area. Here too they established their first churches, Allen Chapel CME (1866) on Broadway, followed by First Baptist Church on Highland (1867). By 1890 North Highland was home to residences, businesses and a “Colored Lodge.”
A number of developers acquired land specifically to sell lots to Blacks for housing. Wiley T. Poynter led the way with the purchase of 65 acres, which he laid out in 53 lots in 1867. Poynterville enclosed the area bounded by Elm, Washington, First, and Evans streets. Later that year, Lewis Haggard and Nelson Ramsey, “men of color,” developed their subdivision, Haggardville, on an eight-acre tract on the east side of First Street, adjoining Poynterville. In 1868 the heirs of John Bruner established Brunerville on the west side of Elm Street. It was framed by Walnut, Upper and Washington. The names Haggardville and Brunerville persisted until the 20th century, when the areas were assumed to be part of Poynterville. In 1868 the Kohlhass family developed an African-American subdivision, Kohlhassville, on Lincoln Street, and a short stretch of East Hickman.

These neighborhoods were blighted by poverty. In 1881 the Winchester churches held a mass meeting “for the purpose of suggesting the best plan for raising funds and provisions for the suffering poor of Brunerville, Poynterville, Haggardville and Kohlhassville.” One committee was appointed to assist those seeking jobs and housing, and another to distribute provisions and fuel.
The communities were also subject to discriminatory practices. A Sun editorial in 1919, referring to the Black communities, pointed out that they pay the same taxes as the whites and “yet have not the same advantages and protections.” As an example, “their streets are almost primitive and in bad weather it is almost impossible to get in and out.” Their water supply was insufficient for fire protection and thus insurance could not be obtained.
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Beginning in the 1930s these low-income, minority neighborhoods were intentionally cut off from lending and investment through a widely practiced system known as redlining. Today many of those same neighborhoods suffer from reduced wealth and greater poverty.
Poynterville, the largest subdivision by area, has always had the largest population, and its area has expanded to the north and west. The early 1900s saw a number of new segregated African-American neighborhoods develop: West Broadway, West Washington, North Maple, North Burns, Oliver, East Hickman from Buckner to the railroad, North Wall Alley, Bell Alley (now Rev. Baker Way), and Kerr Alley (now Hopkins Lane). Most of these neighborhoods continued to grow and become more prosperous throughout the 20th century.
Businesses
Black businesses were identified by searching through the collection of city directories at the library. The main commercial area was always along West Washington Street and, to a lesser extent, North Maple and West Broadway. Washington Street went through a number of ups and downs. In 1908 there were eight businesses: a coal yard, livery stable, restaurant, barbershop, three groceries, and a saloon met much of the community’s needs.
In 1914 there were 20 businesses on Washington, mostly of the same types with addition of two boarding houses and an undertaker. That number plummeted to five in 1940. One possible explanation may be that during the pre-war period, the country was still in the throes of the Great Depression, which had its most serious impact on the most impoverished citizens. Another factor may be that Winchester’s Black population decreased by nearly 50 percent in the three decades from 1910 to 1940.
By the 1950s the number of Washington Street businesses had increased to the low teens. Those numbers were maintained until the late 1980s, when strict code enforcement and urban renewal took their toll. The last to go were Ann and P. J. Washington’s poolroom (1994) and the American Legion building at the corner of Washington and Maple (2016). Markers and memorials in Heritage Park now celebrate this once thriving commercial area that has disappeared.

