Black History

Spottswood Poles

Spottswood Poles

A Winchester native, Spottswood Poles was a decorated WWI veteran (Harlem Hell Fighters) and legend in the Negro League (baseball). 

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Painting of Ruth's Tea Room

Ruth Jackson & Ruth's Tea Room

  • Ruth Jackson owned and operated Ruth's Tea Room on the corner of S. Kent and E. Cecil Streets.
  • Ruth's Tea Room was known as a welcoming place for people of all ages, races, social groups, and income levels. Discrimination of any kind was not tolerated.
  • Parents knew that their children were safe when they would hang out at Ruth's Tea Room.


Old Stone Church

Old Stone Church

  • Old Stone Church, built in 1788, is early example of lower Shenandoah Valley ecclesiastical architecture.
  • Originally a Presbyterian Church meeting house serving substantial Scotch-Irish immigrants settling in Winchester area after migrating south from PA.
  • Revolutionary War hero Daniel Morgan was among Presbyterians who attended there. He was originally buried in the cemetery beside the building in July 1802. His grave stone was severely damaged during Civil War (mainly from soldiers from both sides chipping away souvenir pieces for keepsakes of a military hero). His gravestone was removed for safekeeping and he was reinterred in Mt Hebron Cemetery in 1868. A statue was erected on the property in his honor.
  • The building is one of the few buildings in that part of the City that survived the Civil War and was heavily damaged during Third Winchester when the Confederate troops retreated back into Town from Berryville Pike (now Berryville Ave and National Ave) and fled Winchester altogether for the very last time in 1864.
  • It is believed that Heyward Shepherd was buried near the church after his death in 1859, but no grave marker remains.
  • In 1858, the Winchester Baptist Church (white congregation) sold it to the Old School Baptist Church of Color.
  • In 1875, Old School Baptist Church of Color leased the building to the City of Winchester to operate the building as a public school for Winchester's black children. That continued as the use until the Douglas School was constructed on N. Kent Street. Dr. Taylor Finley taught there and John Kirby attended school there.
  • In 1932, the trustees of the former Old School Baptist Church sold the building back to First Presbyterian Church. That is when a significant restoration of the badly deteriorated building started to take shape. In 1941, they gutted the building and recreated a church layout that would have been in the building in the 1700s. They finished that project in 1950.
  • In 1976 and 1977, the structure was added to the Virginia and the National Register of Historic Places.

Old Douglas School photo

Douglas School


Sara Winifred Brown

Sara Winifred Brown

  • Sara was born in Winchester in 1868.
  • She was a prominent African-American teacher and doctor.
  • In 1908, Howard University hired her to lecture on gynecology as she continued to practice medicine and teach high school biology.
  • In 1910, she held found the group that would later become the National Association of University Women.
  • During WWI, Sara was one of 50 women chosen to be a part of the “Flying Squadron.”
  • In 1924, she became the first woman to serve as an alumni trustee of Howard University.

John Kirby

John Kirby

  • John Kirby was born in Winchester in 1908.
  • He was raised by Reverend Washington Johnson living at 442 N. Kent Street after his mother died.
  • At age 9, he learned to play the piano and trombone and moved to Baltimore, MD.
  • In the 1920s, he learned to play the tuba and bass.
  • Played bass with many noted musicians in jazz bands in major U.S. cities including New York City. 
  • Died at age 43 in Hollywood, CA in 1952.

Dr. Taylor Finley

Dr. Taylor Finley

  • Dr. Finley was Winchester’s only black dentist beginning in 1928.
  • He was also a science teacher at the Douglas School and founded the Douglas Alumni Association.
  • Dr. Finley also operated a recreation center where Ray Charles, Fats Domino and James Brown performed.
  • He was the grandfather to the first black man elected to Winchester City Council.

Robert Orrick

Robert Orrick

  • A prominent black citizen of Winchester, Robert Orrick was born into slavery in 1841.
  • He later owned several businesses, became a minister and gave back to his community.


Heyward Shepherd sitting on a luggage cart

Heyward Shepherd

  • Heyward Shepherd was a free Black man living with his wife and five children on N. Kent Street in Winchester in the mid-1800s.
  • He was employed in Harper’s Ferry to transfer baggage between B&O Railroad and Winchester & Harper’s Ferry Railroad.
  • Sadly ironic, he became the first victim of John Brown’s raid on the arsenal at Harper’s Ferry. He was an innocent bystander shot in the back by one of Brown’s raiders on the night of October 16, 1859.
  • He was the subject of controversial monument erected in 1931 by UDC to promote the "Lost Cause" movement. The monument portrayed him as a “Faithful Slave” even though he was a free black man.

Thomas Laws

Thomas Laws

  • Thomas Laws was a slave during the Civil War. 
  • He regularly crossed CSA lines to sell vegetables in Winchester.
  • He also served as messenger between Union General Sheridan and Quaker spy Rebecca Wright in 1864.
  • HIs actions provided Sheridan with proof of rumors about reduced CSA forces in Winchester resulting in a decision to attack CSA Gen. Jubal Early and end Confederate occupation of Winchester forever.

Tell Us Your Story

Do you have a Winchester Black History story to tell? We'd love to hear it! Send your story to pio@winchesterva.gov