For the rest of his life, he remained a farmer, with the exception of two spells of seafaring as master of merchantmen, first of the "General Washington" and then of the "St. Clair". With the formation of the Ohio Company of Associates in 1788 and the initial westward migration into that territory, Whipple and his family became pioneers on the American frontier and were among the founders of the town of Marietta, Ohio, and the first named proprietor of Charleston, Vermont.