Map of the African American Heritage Trail

As Black History Month winds down, I’m remind­ed of a cou­ple of columns I wrote last February about my tour of Winchester’s African-American Heritage Trail.

I learned so much about the rich his­to­ry of African Americans in Clark County through the years. I’d like to recount a few high­lights of what I learned and wrote about last February.

Just before the Civil War, about 5,000 enslaved peo­ple — some 40% of the pop­u­la­tion — lived in Clark County. There were “slave auc­tions” right here in our county.

Imagine that — human beings being bought and sold like cattle.

During the post-Civil War “Jim Crow” era, most American cities — includ­ing Winchester — had seg­re­gat­ed schools, church­es, busi­ness­es and recre­ation areas. In Winchester’s thriv­ing Main Street busi­ness dis­trict, blacks were not welcome.

As a result of seg­re­ga­tion, there was a flour­ish­ing Black busi­ness dis­trict along West Washington Street. Known as Poynterville, the area was home to dozens of busi­ness­es owned and run by black entre­pre­neurs. These firms includ­ed gro­cery and retail stores, pro­fes­sion­al offices, restau­rants, schools, pool halls and many more.

Our com­mu­ni­ty has had its share of Black civ­il rights pio­neers such as Jennie Bibbs Didlick and the Rev. Henry Baker. Baker was a pas­tor, city com­mis­sion­er, and mem­ber of the Kentucky Civil Rights Hall of Fame. He helped inte­grate Winchester’s schools in 1956, and today Baker Intermediate School stands as a trib­ute to his tenacity.

Before the land­mark 1954 Brown v. Board of Education rul­ing by the U.S. Supreme Court, edu­ca­tion in most of America was seg­re­gat­ed. This includ­ed Clark County.

Some of the schools for “col­ored chil­dren” as they were known, includ­ed the Freedmen’s School, Winchester Colored School, and Oliver Street School. There were many col­ored schools in rur­al Clark County as well, includ­ing three “Rosenwald Schools,” fund­ed by a part­ner­ship between the local black com­mu­ni­ty and the Julius Rosenwald char­i­ta­ble fund.

The point of seg­re­gat­ed schools, accord­ing to their pro­po­nents, was to main­tain sep­a­rate facil­i­ties for Blacks while main­tain­ing “sep­a­rate but equal” facil­i­ties and resources. Needless to say, the “equal” part of that equa­tion was sel­dom — if ever — met.

Today in the US, inte­gra­tion is the law. However, in prac­tice, many schools have lit­tle or no diver­si­ty, reflect­ing our still too seg­re­gat­ed com­mu­ni­ties. And despite the best efforts of many edu­ca­tion pro­fes­sion­als, achieve­ment gaps remain. We need to do a bet­ter job of edu­cat­ing all chil­dren to high standards.

African Americans have par­tic­i­pat­ed in every mil­i­tary con­flict in our nation’s his­to­ry. Most of those bat­tles were fought in times when they were sep­a­rat­ed from their fel­low white sol­diers and rel­e­gat­ed to sec­ond-class status.

Black Army reg­i­ments were formed in the after­math of the Civil War pri­mar­i­ly to fight native American tribes, who called the units “Buffalo Soldiers.” There were 33 mem­bers from Clark County serv­ing in these units.

One mem­ber was Jacob Wilks, who also served in the Civil War for the Union. Other locals include John Sidebottom, who served in the Revolutionary War and saved the life of future President James Monroe, and World War II vet­er­an Thomas B. Miller, a mem­ber of the famous Tuskeegee Airmen, who went on to be a suc­cess­ful busi­ness per­son in Winchester.

After the Civil War, Black peo­ple were pressed to find homes and jobs to sus­tain their fam­i­lies. Working in ser­vice indus­tries and on farms, they found­ed sev­er­al com­mu­ni­ties where they oper­at­ed their own busi­ness­es, church­es, schools and cemeteries.

Some of the com­mu­ni­ties include the afore­men­tioned Poyntersville, Haggardsville, Brunerville, Lisletown and the North Highland Street area, among others.

Three men coached at Oliver Street School and won state cham­pi­onships in mul­ti­ple sports, includ­ing foot­ball and boys and girls bas­ket­ball. They were E.J. Hooper, Hubert Page, and Joe Gilliam, who lat­er went on to coach foot­ball at Tennessee State University.

Two of the many out­stand­ing Black ath­letes to come from Clark County are hon­ored on the trail. They are Robert Brooks and Wilbur Hackett Jr.

Brooks was a mul­ti-sport ath­lete at Oliver before deseg­re­ga­tion allowed him to play at the old Winchester High his senior sea­son. There he led the bas­ket­ball and foot­ball teams to their first win­ning sea­sons in many years. Brooks went on to play col­lege and pro­fes­sion­al football.

Hackett was among the first Black ath­letes to com­pete for the University of Kentucky in foot­ball. A mem­ber of the UK Athletics Hall of Fame, Hackett’s stat­ue now stands at the university’s foot­ball stadium.

In the ear­ly days of horse rac­ing in Kentucky, most jock­eys were Black, and many were natives of Clark County. It is pos­si­ble that famed African-American jock­ey Isaac Murphy hailed from Clark County. As doc­u­ment­ed in a 2020 arti­cle in the Sun, some peo­ple think the man who won three Kentucky Derbies grew up on a near­by farm.

I’ve learned a lot about my African-American neigh­bors and their rich his­to­ry. The Bluegrass Heritage Museum has doc­u­ment­ed much more of this his­to­ry. I encour­age you to vis­it the muse­um and check out their web­site, includ­ing a whole sec­tion on Black history.

This arti­cle appeared in The Winchester Sun on February 26, 2021.

  • Pete Koutoulas

    Pete is an IT pro­fes­sion­al work­ing in Lexington. Formerly of Campton, he and his wife have lived in Winchester since 2015. Pete is a for­mer week­ly news­pa­per pub­lish­er and for­mer colum­nist for the Winchester Sun. These days, when not work­ing he can often be found on his back porch read­ing or writ­ing, in the back­yard tend­ing to his toma­to plants, or put­ter­ing around in his garage or work­shop. Reach Pete at