At least one of his vessels delivered to his shop at the New Haven wharf a shipment of Chinese porcelain, silk, spices, and tea.

Timothy, Mary's maternal uncle, was a successful businessman, serving as a director for a bank and an insurance company.

[6] In 1804, Stephen F. Austin moved from Missouri Territory to live with the Phelpses; Mary's eleven-year-old cousin had grown up in the frontier west before his father sent him to New Haven for an education.

Mary was engaged that year to Horace Holley, a seminary student and aspiring minister, and they were married on 1 January 1805.

[8] For the first few months of their marriage, the Holleys lived in his father's home in Salisbury, Connecticut, while he researched, wrote, and delivered sermons as a guest at a local church.

He accepted the suggestion of the president of the Yale Seminary and took the position as minister of a church at Greenfield Hill in Fairfield County, Connecticut.