Grant E. Lilly was born in Estill County on February 27, 1865. He was the son of Colonel Henry Clay Lilly, a circuit judge of the Irvine district and a colonel in the 14th Kentucky Calvary, United States Army, during the Civil War, and Catherine Tracy, a member of a pioneer Pennsylvania family whose descendents moved to Kentucky.

Mr. Lilly received his early education in the private school in Madison County at College Hill and Dr. Elliot's School for Boys at Kirksville. He attended Central University in Richmond and was a honor graduate of the University of Michigan Law School in 1889. Upon completion of his studies at Ann Arbor, he returned to Irvine where he served as county attorney of Estill County. He had also taught school before receiving his law training. Like his father, Lilly became active in the Republican Party, but around 1900 switched his allegiance to the Democratic Party.

Anna Dudley McGinn Lilly was born February 27, 1872, in Maysville, Kentucky, the daughter of the Reverend John Bolivar McGinn and Mary Elizabeth Sheppard McGinn. She spent her early life in Versailles, where her father was minister of the Christian church.

On October 19, 1883, Grant E. Lilly and Anna D. McGinn were married in Versailles. They had one daughter, Austin Page Lilly; a son, John Marion Lilly; and a younger son, Grant Lilly, Jr., who died at the age of 12 in 1916. After marrying, the Lillys lived in Richmond where they were involved in numerous civic projects and organizations. Lilly was one of the leaders, along with Dr. Hugh McClellan, Col. C. E. Woods, and Col. N. B. Deatherage, in a local option fight prior to prohibition. Lilly as a member of the Prandennial Club, a charter member of the first Chamber of Commerce organized in Richmond, as well as one of the sponsors of the Richmond Chautauqua. He also was a member of the American Bar Association, the Kentucky Bar Association, and one of the organizers of the Madison Bar Association.

He was owner and editor of three newspapers, the Madisonian, which he founded, the Richmond Climax, and the Kentucky Register which later were merged into the Richmond Daily Register. The Kentucky Register was purchased by Lilly for his wife who was its editor.

In 1918 the Lillys moved to Lexington. Lilly was elected president of the Gas Consumers League which worked for the taxpayers in an effort to reduce the price of natural gas. Lilly ran for mayor of Lexington in 1927 and lost.

Anna Lilly was very interested in Central Kentucky politics and civic affairs. She became affiliated with the Daughters of the American Revolution in 1912 as a member of the Boonesborough Chapter, later transferring her membership to the Lexington Chapter, of which she subsequently became regent. Mrs. Lilly was regent of the Kentucky DAR from 1923 to 1926. In 1928, she spearheaded a drive to have the state legislature approve a bill designating "My Old Kentucky Home" as the official state song. The first rendition of Stepen Foster's composition was sung on Sunday, April 15, 1928, at the Valley Forge, Pennsylvania. The occasion was the dedication of the Kentucky bell in the memorial chapel there. The bell in the carillion at Valley Forge was purcased with $1000 raised by Mrs. Lilly and a committee of the DAR. She was an honorary life regent of both the state and Lexington DAR.

With the advent of women's suffrage in 1920, Mrs. Lilly organized the first Woodrow Wilson Club and in 1932 she founded the Roosevelt Democratic Club of Richmond. Twice she was county associate chairman for the Fayette Club of Kentucky. She actively supportive Alben Barkley's several successful senatorial campaigns.

Mrs. Lilly was four times president of the Richmond Women's Club; a member of the Women's Club of Central Kentucky; a charter member of the Madison County Historical Society, the Lexington McDowell Music Club and the Bradford Club of Lexington; and held membership in the Huguenot Society of South Carolina, the Colonial Dames of Kentucky and the state and state and national officers' club of the DAR. She was organizing president of the Kentucky branch of the Huguenot Society of the Founders of the Manakin Towne and of the Paul Revere chapter of the Children of the American Revolution.

During Lexington's sesqui-centennial celebration, Mrs. Lilly was chairman of the Hall of Fame, which featured an outstanding collection of historical items. She was instrumental in the naming of Henry Clay High School and served on the board of the Henry Clay Memorial Foundation when it began work on making Ashland a state shrine.

She was a member of the board of direcotrs of the Pioneer National Monument Association which acquired the Blue Lick battlefield and other historic spots in Kentucky. She eaded the Madison County Liberty Loan and War Savings stamp drive in World War I and served as co-chaiman of many Madison Red Cross campaigns. She worked with the NRA in the 1930s and was a honorary member of the VFW during World War II.

Grant Lilly died January 5, 1940, and Anna D. Lilly died July 30, 1948. Both are buried at the Richmond cemetery. Austin Lilly died September 18, 1991, in Georgetown, Kentucky.