On the trail of African American history

This sto­ry is an update of one I wrote for The Winchester Sun in February 2020, with new photos.

In ear­ly 2020, I decid­ed to final­ly do some­thing I’d meant to do for some time. I was down­town just strolling around and decid­ed to tour the African American Heritage Trail. 

The Winchester Black History & Heritage Committee estab­lished the trail in the down­town area. The trail con­sists of eight way­points or sta­tions that stand at his­tor­i­cal­ly sig­nif­i­cant loca­tions around the down­town area. 

Since I was already on the rear lawn of the cour­t­house just off Wall Street, I start­ed my tour there. I grabbed a brochure from the dis­play and snapped a pho­to of the ori­en­ta­tion map to refer to as I walked the trail. 

I first noticed that the var­i­ous sta­tions along the trail are ordered rough­ly chrono­log­i­cal­ly rather than geo­graph­i­cal­ly. This means tak­ing the path in order from sta­tion num­ber one through eight caus­es you to zigzag amid the down­town area, often back­track­ing and retrac­ing your steps. You might want to re-order your trek if you’re short on time or have mobil­i­ty issues. 

I decid­ed to view the sta­tion as intend­ed, to fol­low down­town Winchester’s Black his­to­ry in order of the peo­ple, places, and events depicted.

The first stop is Heritage Park at 131 W. Washington St., near the inter­sec­tion of Maple St. Like all the oth­er sta­tions along the trail, this one fea­tures a dou­ble-sided plaque with infor­ma­tion about the par­tic­u­lar location. 

This stop com­mem­o­rates the Black busi­ness dis­trict that once thrived along West Washington Street. According to the plaques at the site, this area—known as Poynterville— once con­tained 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. 

Nearby, I found sta­tion num­ber two, at 43 N. Maple Street, near the present-day loca­tion of Central Bank. Here, I learned much about life dur­ing pre-eman­ci­pa­tion times for Black folks in Winchester. 

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

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

I also learned about suc­cess­ful black mer­chants, sol­diers, and farm­ers. People like Peter Bruner, Moses Robinson, Aaron Abbott, and Fanny Cole. 

Next, I head­ed to sta­tion num­ber three, at 121 W. Broadway—the site of Broadway Baptist Church, now known as Broadway Missionary Baptist Church. Here, I learned more about the rea­sons for the sep­a­rate com­mu­ni­ties for Black folks. 

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

I learned about local African American civ­il rights pio­neers such as Jennie Bibbs Didlick and Rev. Henry Baker. 

Rev. Baker was a pas­tor, city com­mis­sion­er, and Kentucky Civil Rights Hall of Fame mem­ber. He helped inte­grate Winchester’s schools in 1956, and today, Baker Intermediate School (where my grand­son attends) stands as a trib­ute to Rev. Baker’s tenacity. 

Speaking of church­es, sta­tion num­ber four stands a few blocks east at Broadway and Highland Street, com­mem­o­rat­ing ear­ly African-American church­es in Winchester. Before the Civil War, enslaved Blacks had to wor­ship at the church­es of their White mas­ters. However, fol­low­ing eman­ci­pa­tion, the freed peo­ple nat­u­ral­ly desired to form their own con­gre­ga­tions. Several such church­es were found­ed in the North Highland area dur­ing that era.

The first of these was Allen Chappel, estab­lished in 1866. The struc­ture still stands at East Broadway and North Highland, where the plaque for sta­tion #4 is placed.  Some oth­ers includ­ed the First Baptist Church and Clark Chappel, both nearby. 

Here, I also learned about anoth­er promi­nent local Black con­gre­ga­tion, Providence Missionary Baptist Church. This church was rur­al, locat­ed on Lower Howard’s Creek off Boonesboro Road on what is today known as Old Stone Church Road. 

Providence is thought to be the old­est church in Kentucky con­tin­u­ous­ly in use. The first church in Clark County, it was formed ini­tial­ly by Whites. The con­gre­ga­tion accept­ed its first Black mem­ber in 1786, mak­ing it an out­lier as one of the ear­li­est inte­grat­ed church­es in the state. 

Nearly a cen­tu­ry lat­er, nine­teen Black mem­bers with­drew from Providence to form their own con­gre­ga­tion. Then, in 1872, after the White mem­bers had moved to a new build­ing, they pur­chased the orig­i­nal stone struc­ture and returned to wor­ship­ping there. The church still meets today in that old stone build­ing on Lower Howard’s Creek.

Educational progress is the top­ic of stop num­ber five along the trail. Located at 30 Oliver Street, 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 Winchester schools for “col­ored chil­dren,” as they were known, includ­ed the Freedmen’s School, Winchester Colored School, and Oliver Street. There were also many “col­ored” schools in rur­al Clark County, 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 Black and White chil­dren 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 of the land. 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 North Maple Street, just across the street from Stock Yards Bank, which until recent­ly was 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, 33 mem­bers from Clark County served 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 Tuskegee Airmen who went on to be a suc­cess­ful busi­nessper­son in Winchester. 

Just a few blocks west on Washington Street is sta­tion num­ber sev­en, com­mem­o­rat­ing 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 North Highland Street area. 

The final sta­tion along the trail takes us back to 30 Oliver Street, 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 coached 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. 

Brooks was a mul­ti-sport ath­lete at Oliver before deseg­re­ga­tion allowed him to play at the old Winchester High his senior sea­son. 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. 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 news­pa­per arti­cle in The Winchester Sun, some 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 sport’s his­to­ry. If it could be doc­u­ment­ed that he came from Clark County, I would love to see a promi­nent and appro­pri­ate mon­u­ment erect­ed in Winchester.

Thanks in part to the African American Heritage Trail, I’ve learned much 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, as has Harry Enoch and oth­er con­trib­u­tors to WinCity Voices.

I encour­age you to vis­it the muse­um and check out their web­site, which includes an entire sec­tion on Black history.

And maybe I’ll see you on the trail soon.