In the fall of 1813, Richardson announced that he was leaving Groton. Although Richardson offered to secure Kendall an apprenticeship with the attorney taking over his practice, Kendall declined the offer. Kendall decided that, with an economic depression afflicting New England and his only patron leaving, it was time to leave Massachusetts. He resolved to relocate to Washington, D.C., and arrived in the city on March 2, 1814. Introduced to numerous politicians by William M. Richardson, who had been elected to the United States House of Representatives, he was hired by Senator Jesse Bledsoe of Kentucky to tutor the Bledsoe children. He left Washington on March 9, traveling by stagecoach to Pittsburgh, Pennsylvania, and then by flatboat down the Ohio River to Cincinnati, Ohio. He largely walked the south to Lexington, Kentucky, reaching the city on April 12.