H.N. (Bert) Woolson was born in 1916 to Dr. and Mrs. A.H. Woolson of Spokane, Washington. After graduating from Gonzaga Law School in 1940, he entered the Office of Strategic Services, where he served for four and a half years. In 1946 he moved to Walla Walla and opened a private law practice in Dayton, Washington. Later he held the position of prosecuting attorney of Columbia County and county coroner, then became the mayor of Dayton in 1964. His paternal grandfather was Albert Woolson.

Albert Woolson (1847-1956), the last living Union veteran of the Civil War, was born in Watertown, New York on February 11, 1847. When he was fifteen, his family moved to Minnesota. In October 1864, he enlisted in the Union army as a volunteer private in Company C of the First Minnesota heavy artillery regiment. He served as a drummer boy in Chattanooga, Tennessee for slightly less than a year.

After his discharge from the army in September 1865, Woolson worked at a variety of jobs, many in the field of engineering. He settled permanently in Duluth, Minnesota in 1905.

He married Sarah Jane Sloper in 1868. Three years after her death in 1901, he married Anna Haugen, who died in 1949. From these two marriages, Woolson had fourteen children. When he died in 1956, six daughters and two sons were still living.

In later years, Woolson gained fame as an active member of the Grand Army of the Republic. He served as Commander of the Minnesota Grand Army of the Republic (GAR) until it dissolved in 1947. In 1950, he became the Senior Vice Commander in Chief of the National Grand Army of the Republic, and its sole remaining member in 1953.

As Woolson passed his 100th year and veterans of the Civil War became scarce, his birthdays drew national attention, with articles about him in newspapers and cards arriving from all across the country, including letters from U.S. presidents. His celebrity status also put him in the spotlight during Memorial Day celebrations and Civil War commemorations.