His mother was on a short visit at the time, and he was brought home to Cheshire soon after where he would grow up.

He studied at Yale Law School graduating 1846 the same year he was admitted to the bar all before he was 21.

He practiced law from 1846 until 1850 in Cheshire, from 1850 to 1858 in Meriden, and thereafter in New Haven, where he resided until his death on March 21, 1896.

In 1866, 1867 and 1870 his fellow citizens, appreciating his quality, elected him a representative from New Haven in the State Legislature.

Mr. Doolittle was appointed by Richard D. Hubbard States Attorney for New Haven, Connecticut 1879,[3] succeeding O. H. Piatt.