Back on the trail of Winchester’s black history

This article appeared in The Winchester Sun on February 27, 2020.

Today we’re concluding last week’s column about my recent visit to the African American Heritage Trail in downtown Winchester. 

Educational progress is the topic of stop number five along the trail. Located at 30 Oliver St., this is the home of the former Oliver Street School for black children. Before the landmark 1954 Brown v. Board of Education ruling by the US 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. 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. 

Oliver Street School, 30 Oliver St., Winchester, Kentucky.
Oliver Street School, 30 Oliver St., Winchester, Kentucky.

The point of segregated schools, according to their proponents, was to maintain separate facilities for blacks and whites 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, being a reflection of 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. 

Moving along to station number six, I learned about the many military contributions of African Americans to our country. This station is located at 102 N. Maple Street, just across the street from Kentucky Bank, which was until recently the site of Tyler Banks American Legion Post 204.

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.” According to the marker at this station, there were 33 members from Calrk County serving in these units. 

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

Just a few blocks west on Washington St. is station #7, which commemorates several post-civil war African American communities 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 profiled at this stop include Poyntersville, Haggardsville, Brunerville, Lisletown, and the N. Highland St. area, among others. 

The final station along the trail takes us back to 30 Oliver St., the former home of Oliver High School. This stop commemorates local African American athletics. Three men coached at Oliver 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 also honored on this marker. They are Robert Brooks and Wilbur Hackett Jr. 

Honoring African American athletes from Clark County.
Honoring African American athletes from Clark County.

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 Kentuck in football. A member of the UK Athletics Hall of Fame, a statue of Hackett 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. This is not mentioned on the trail but worthy of note is the possibility that famed African American jockey Isaac Murphy may have hailed from Clark County. As documented in a recent article in the Sun, some people think the man who won three Kentucky Derbies grew up on a nearby farm.

Murphy is thought by many to have been the greatest jockey in the history of the sport. If it could be documented that he did indeed come from Clark County, I would love to see a prominent and appropriate monument erected to him in Winchester.

I’ve learned a lot about my African American neighbors and their rich history. And this is only the tip of the iceberg. The Bluegrass Heritage Museum has documented much more of this history. I encourage you to visit the museum and check out their website, which includes a whole section on black history. 

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