Octavius Pickering was born in Wyoming, Pennsylvania, on September 2, 1791. After graduating from Harvard in 1810 and studying law, he was admitted to the Bar of Suffolk County in 1816. Mr. Pickering practiced law in Boston and assisted in reporting the proceedings of the Massachusetts Constitutional Convention in 1820. From 1821-1825, he served as a trustee of the Social Law Library. In 1822, Mr. Pickering was appointed the Reporter of Decisions for the Supreme Judicial Court. He served as Reporter from 1822 until 1839, during which time he reported decisions that comprise twenty-four volumes of the Massachusetts Reports.

Mr. Pickering also pursued an interest in natural history as a fellow of the American Academy of Arts and Sciences and a founder of the predecessor to the Boston Society of Natural History. He also was the co-author in 1821 of "A Report of the Trial by Impeachment of James Prescott," and he prepared the first of a four-voume set about the life of his father, a well-known military officer and statesman, entitled "Life of Timothy Pickering by His Son."