Reuben Ruby was a hack driver. Hack drivers were persons who operated stage coaches for hire (the Uber of its day). He is credited with being the first Hack driver in Maine. Being a hack driver made it easy for him to work as a conductor on the Underground Railroad – transporting persons fleeing slavery to safe locations.
In 1832 he drove abolitionist William Lloyd Garrison around the city and facilitated a meeting between Garrison and other Black leaders.