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A Glimpse Into Loudoun’s African American History: A Research Journey with Oral Histories

For some time now, the Loudoun Museum has been conducting research for an exhibit that would tell the story of African American business owners in Loudoun during the Jim Crow era. (Spoiler: There were many). Our starting point is information we have about three African American businesses that were housed in the museum’s building during the 1920s and 1930s, most notably the Dew Drop Inn. Beyond this information, however, we have little in our collection that would allow us to tell this overlooked story of perseverance and success, so we had to branch out.

The museum is fortunate to be part of a network of history and cultural heritage organizations in the county that have vast repositories of historical information and support one another through an open exchange of information. Leesburg’s Thomas Balch Library is one of these and is an absolute treasure for amateur and professional historians alike. Its diverse collections allow the museum to glean facts and context about artifacts in our collection so that we can accurately exhibit and interpret Loudoun’s history, culture, and treasures.


As a volunteer with the museum, I have had the privilege to review almost three dozen oral histories in the library’s collection while doing background research for the exhibit on African-American businesses. These oral histories, gathered by the Black History Committee of the Friends of the Thomas Balch Library starting in 2000, offer a rare glimpse into the lives of African Americans in Loudoun during the first half of the 20th century. In many cases, individuals who were interviewed died within a few years of sharing their stories. Had these oral histories not been recorded and painstakingly transcribed, an entire chapter of Loudoun’s history would have disappeared forever.

Many of the oral history interviews followed a set order of questions, beginning with brief, factual questions about a person’s biography and progressing to more open-ended questions, including about racial relations. The absence of follow-up questions can be maddening. In one instance, a woman described growing up in deep poverty in southeastern Virginia. She said the turning point in her life came when she moved to Washington, D.C., at the age of 19 and learned dressmaking skills. How did she get to Washington? Why Washington? Did she have family there? Those answers are missing, but somehow this sharecropper’s daughter managed to send two of her five children to college. One graduated from Harvard.[1]                                                             

Oral histories do not paint a complete historical picture. They provide just one of many glimpses into the past, and a deeply personal one at that. One by one they provide the pieces that fill in a puzzle. Some pieces, though, remain hard to place within the border, and frustratingly without enough detail to indicate where they fit. 

Searching for Honey

For me, one vexing puzzle piece was a restaurant called Honey’s. One individual’s oral history mentions that at some point, probably in the 1930s or 1940s, Leesburg had as many as four African American–owned restaurants.[2] The Dew Drop Inn was one of these; a place called Honey’s in Leesburg’s Black Bottom neighborhood, “with a billiards room downstairs,” was a second;[3] a restaurant on W. Loudoun Street in one of the buildings owned by the wealthy Diggs family was a third; [4] the fourth has been lost to time.


Another oral history provided a tantalizing clue. In her interview, Mary Frances Wiley Webb (1916-2009) said her mother, Caroline Morris Wiley Pinkett (1894-1939), had at some point run a restaurant in “the big house on the corner of Royal and Wirt,” in Black Bottom.[5] Ms. Webb inherited her mother’s culinary skills. She worked as a cook for a wealthy White woman in Leesburg for more than 50 years,[6] emphasizing to her interviewer that she “never cleaned.” From the timeline, it appeared that Ms. Webb’s mother’s restaurant would have been too early to be Honey’s, so the search continued.


For more than a year, I had no other information about Honey’s. Then last spring, I had the opportunity to go on James Roberts’s historical walking tour, sponsored by the Thomas Balch Library. Mr. Roberts, born in 1936, is an African American man whose family has deep roots in Leesburg. His twice-yearly walking tour—another form of oral history—focuses on the Leesburg of his youth, during segregation. When we passed the intersection of Royal and Wirt Streets, I asked whether he recalled or knew of a restaurant called Honey’s. He spun around and pointed to a big brick house on the corner: “That’s where it was. It was owned by James Wiley. W-I-L-E-Y,” he helpfully spelled out. I discovered that James Wiley (1913-1970) was one of Ms. Webb’s brothers, but nothing directly linked him to Honey’s.[7] 

“The big house on the corner of Royal and Wirt.” Photo by the author.


More months passed before Honey’s piece of the puzzle fell into place. I was walking past Mt. Zion Cemetery, another kind of historical repository, and noticed a headstone I had missed before: Robert “Honey” Wiley (1918-2004). Bingo. I was able to look at his draft registration card from 1940 and saw that he had identified himself as a partner of a “lunchroom,”[8] the same term the Dew Drop Inn’s first proprietor had used to describe that establishment.[9] He was a brother of Mary Frances and James and gave his address as 127 W. Royal Street, close to the red brick building that James Roberts had pointed out to me.[10]

Headstone for Robert “Honey” and Mary Elizabeth Wiley, Mt. Zion Community Cemetery, Leesburg. Photo by the author.

The Wileys’ story is one thread in the larger tapestry of Loudoun’s African American businesses in the first half of the 20th century and, as always, there is more to learn. It seems that the mother of the Wiley siblings had use of the handsome brick home at the corner of Royal and Wirt through an arrangement with its owner, John Harrison Leslie (1871-1932),[11] a White man who owned several other properties in Black Bottom.[12] To understand more about him and that arrangement, I will need to go to the Loudoun County Courthouse, which has one of the most complete collections of historical records in Virginia. I know the answers will be there... the oral histories point the way.


If you know anything about Honey’s, or the Wiley family, or any other of Loudoun’s early, African American–owned businesses, please share their stories with the Loudoun Museum.

[1] Mae Eva Johnson (1918-2010), Black History Committee Oral History Project, 2000-2006 (M 012), Thomas Balch Library, Leesburg, VA.

[2] Frank Watkins (1922-2018), Black History Committee Oral History Project, 2000-2006 (M 012), Thomas Balch Library, Leesburg, VA.

[3] Black History Committee of the Friends of the Thomas Balch Library, Loudoun County’s African American Communities: A Tour Map and Guide, by Deborah A. Lee, 2004, p. 13.

[4] Frank Watkins (1922-2018), Black History Committee Oral History Project, 2000-2006 (M 012), Thomas Balch Library, Leesburg, VA. These buildings were torn down in the late 1950s or early 1960s to make way for a parking garage.

[5] Mary Frances Wiley Webb, (1916-2009), Black History Committee Oral History Project, 2000-2006 (M 012), Thomas Balch Library, Leesburg, VA.

[6] Loudoun Funeral Chapel obituary, 4 May 2009.

[7] 1930 Census record for Caroline Morris Wiley Pinkett, accessed through

[8] Accessed through

[9] 1930 Census record for Hamilton Fink (ca 1872-1931). Accessed through

[10] A house at 127 W. Royal Street is no longer there.

[11] Mary Frances Wiley Webb (1916-2009), Black History Committee Oral History Project, 2000-2006 (M 012), Thomas Balch Library, Leesburg, VA.

[12] Frank Watkins (1922-2018), Black History Committee Oral History Project, 2000-2006 (M 012), Thomas Balch Library, Leesburg, VA.

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