After the Civil War, Ashford, became a surveyor for the Beaverton railway and joined the Prince of Wales' Canadian Dragoons where he made Captain.

In 1884, his brother and future Attorney General of Hawaii, Clarence W. Ashford, invited him to visit Honolulu.

Shortly after becoming Colonel, a group of conspirators within the Missionary Party wanted to annex Hawaii to the United States.

After the Overthrow of the Hawaiian monarchy, Ashford returned to Hawaii and retired from his position as commander of the Rifles.

The counter-revolution ended in failure in 1895 and Ashford was charged with misprision of treason and received one year in prison and a $1000 fine.