Russell Gregg was born on April 6, 1890 to Edgar Bentley and Mary Nichols Gregg at his family farm west of Hamilton, Virginia. He worked as a farmer with his brother while becoming an amateur photographer. He worked for the Loudoun Times-Mirror as a photographer, specializing in high school classes. He married Anne Pierce in October of 1917; they did not have any children. For the last few years of his life, Gregg lived with his niece, Mary Gregg Pancoast Reynolds. He died on December 16, 1980 in Purcellville, Virginia.

Loudoun County in the 1920s, 1930s, and 1940s had a stable population of approximately 20,000 people. The county was predominately agricultural, with more than 2000 farms in 1920. In 1920-1921, Loudoun was negatively impacted by the stabilization of Europe after World War I, which had previously depended on America farms for food and goods. By 1922, prices had returned to pre-war levels, and dairy became a large part of Loudoun's economy. The W&OD Railroad influenced the growth of industry in Loudoun, as well as the continued support of the dairy market. Loudoun County was not immediately affected by the stock market crash in 1928; the drought of 1930 brought the Great Depression to Loudoun. Most relief was provided by the Virginia Department of Agriculture, but the number of farms dropped below 1700. The Rural Electrification Administration brought electricity to Loudoun in 1935, making domestic and agricultural work easier. World War II brought about a revival to the economy, as Loudoun farms and industries were once again needed to support the war effort. In addition to supporting the war at home, 3000 Loudoun men signed up for the draft before the age limit was lowered from 21 to 18 years. Fifty-one of those men died in the war.