- Each of the Dale brothers attended high school, most likely at Stone High School.
- According to the 1920 census, Woodrow's father, Henry Brantley Dale, was a self-employed farmer.
- Woodrow would have graduated high school in 1930, most likely.
- His education stopped at high school graduation, with a four-year experience and a diploma.
- Between his graduation and his enlistment in the U.S. Army, Woodrow served as the assistant to the county agent.
- In the 1940 census, he is listed as being in beat 2, range 12, in Stone County, Mississippi and was classified by this census as a (white) citizen.