Born in Gorham, Maine (then a district of Massachusetts) to Stephen Longfellow and Patience Young Longfellow, Longfellow graduated from Harvard University in 1798. He studied law and was admitted to the bar in 1801 and commenced practice in Portland, Maine. He married Zilpah Wadsworth and, with her, had several children, including the future poet Henry Wadsworth Longfellow.
He served as member of the general court of Massachusetts in 1814 and 1815. He belonged to the Federalist Party and was a delegate to the Hartford Convention in 1814 and 1815. He also served as a Federalist presidential elector in 1816.
Longfellow was elected as an Adams-Clay Federalist to the Eighteenth Congress (March 4, 1823 – March 3, 1825). He was not a candidate for renomination in 1824 and resumed his law practice for a time.
He served as member of the state house of representatives in 1826. He served as overseer of Bowdoin College, Brunswick, Maine from 1811 to 1817 and was a trustee of the college from 1817 to 1836. He supported the Portland Athenaeum. He also served as president of the Maine Historical Society in 1834.
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