A longtime resident of Maine's largest city,
Portland, Ruby was the state's first
hack driver and hack stand owner. His hack stand operated at the Elm Tavern, which was located at the corner of Temple and Federal Streets in Portland's
Old Port. It was through his hack business that he became involved in transporting people on the
Underground Railroad. By the 1830s, he owned multiple carriages. In 1832, he drove
William Lloyd Garrison around the city in his carriage during Garrison's visit to Portland. Afterwards, Garrison had dinner at Ruby's Portland home with other leaders of the African-American community. Ruby also had various other professions besides hack driving. In 1820, Ruby was working in Portland as a waiter. == Abyssinian Meeting House ==