[3] At the age of sixteen, he moved to Hartford to begin his formal art training under the tutelage of Joseph Steward, a prominent local artist.

While in Hartford, he had made the acquaintance of congressman John Rutledge, Jr., who was impressed with his work and, in 1803, invited him to come to Charleston, South Carolina.

Between his artistic activities, he met and married Elizabeth Wood of Liverpool in London in 1808, and the couple journeyed back to New York City to live.

Three years later William Jewett (d. 24 March 1874),[7] a young coach painter from New London, Connecticut, who wanted to be a fine artist, approached Waldo and asked to be taken in as an apprentice.

[5][10] As a team, it is generally believed that Waldo painted the head and hands of their subjects, while Jewett filled in the clothing and draperies.