ay R. Sherwood was born in New York City in 1885 and ran away from home and went to sea as a young man. He later apprenticed as a trainman and also worked on fishing boats in southeast Alaska. Agnes Banner was born in Victoria, British Columbia, Canada in 1894 and married Jay in Victoria, British Columbia in 1913.

After he served in World War I in France, Jay worked on several railroads in California. In 1925 he moved his family to Anchorage, where he did construction work prior to hiring on with the Alaska Railroad. He did some commercial fishing and also some mining to fill in between jobs.

The Sherwoods had five children: Elsie, born in 1918; Jay R., Jr., born in 1920; Ruth, born in 1921; Warren, born in 1924 and Morgan, born in 1929. In 1932 Jay R., Sr. was hired permanently with the Alaska Railroad and stayed with them until he retired in 1947 as a conductor. Agnes was known as an excellent seamstress and while raising the children she was active in the Order of the Eastern Star. Jay, Sr. died in 1964, and Agnes Banner Sherwood died in 1969. They are both buried in Escondido, California

Daughter Elsie Sherwood Mazur had five children; Mary A., Stanley F., John R., Michael A. and Elizabeth. She died in 1999. Son Jay R., Jr. had three sons; Jay R. III, Kenneth H. and David. Daughter Ruth Sherwood Holman had two children, Paul and Lee Carol Holman Patterson. Ruth died in 1998 and is buried in Ephrata, Washington. Son Morgan had no children and died in 2000. He is buried in Davis, California.