Born in Cheshire, Connecticut on May 18, 1754, Doolittle developed his skills in copper engraving through self-study and apprenticeship.

Under the leadership of Captain Benedict Arnold, the company arrived in Cambridge, Massachusetts ten days after the Battles of Lexington and Concord, marking theoutset of the Revolutionary War.

[1] Upon arrival, Doolittle obtained leave to inspect the battle site, accompanied by Ralph Earl.

Doolittle conducted interviews with colonial militants and local residents to establish the scene while Earl surveyed the site and made drawings.

[4] From these drawings, Doolittle made at least four engraved copper prints of the battle, which were advertised for sale in the December 1775 Connecticut Journal.