1930 U.S. Census, Baltimore City, Maryland
8th Ward, Enumeration District 108
1719 Lanvale Street
Ashley, Upton F., head, rents, home value $4500, male, white, 35, married, age at first marriage 24, not in school, can read and write, born in Maryland, both parents born in Virginia, speaks English, painter, wage worker, at work previous day, veteran of the World War
Ashley, Bertha J., wife, female, white, 31, married, age at first marriage 16, not in school, can read and write, born in Maryland, both parents born in Maryland, occupation house maker
Ashley, Catherine, daughter of h[ead of household], female, white, 14, single, in school, can read and write, born in Maryland, both parents born in Maryland, speaks English, no occupation
Ashley, Robert, son of h[ead of household], male, white, 13, single, in school, can read and write, born in Maryland, both parents born in Maryland, speaks English, no occupation
Williams, Samuel T., boarder, male, white, 74, widowed, age a first marriage 22, not in school, can read and write, born in Maryland, both parents born in Maryland, speaks English, occupation illegible, wage worker, at work previous day, not a veteran

1940 U.S. Census, Winchester City, Virginia
Enumeration District 124-6
503 Highland Avenue, owned home valued at $4000
Ashley, Laura V., head, female, white, 70, widowed, not in school, highest level of education 4th grade, born in Virginia, employed for pay, grocer at grocery, 0 weeks worked in 1939, has other income
Ashley, Upton, son, male, white, 45, married not in school, highest level of education 6th grade, born in Virginia, not employed for pay, seeking, work, occupation painter, 0 weeks worked in 1939, has other income
Ashley, Bertha, daugher in law, female, white, 40, married, not in school, highest level of education 6th grade, born in Maryland, not employed or seeking work, engaged in home housework
Riley, Ruth, grandchild, female, white, 13 single, in school, highest level of education one year of high school, born in Maryland, residence in 1935 Baltimore, Maryland
Riley, Esther, grandchild, female, white, 11, single, in school, highest level of education 5th grade, born in Maryland, residence in 1935 Baltimore, Maryland

On 27 April 1942, Upton Smith Ashley registered for the World War II draft, giving his address as 701 Yuma Street, S.E., Washington, D.C.; mailing address 503 Highland Avenue, Winchester, Virginia; age 49; born 4 July 1893; born in Baltimore, Maryland; person who will know your location Mrs. Bertha V. Ashley of 503 Highland Avenue, Winchester, Virginia; employer U.S. Government; place of work Shop #11, Navy Yard, Washington, D.C.; white; 6’-1/4”; weight 210; brown eyes; brown hair; ruddy complexion. [World War II Registration Draft Cards, 1942.]