Ogilby's early career as a dancing master and theatre owner in Ireland, crowned by the success of a theatre he built in Dublin, ended in 1641 with his finances ruined by the outbreak of the English Civil War. Returning destitute to England, he learned Greek and Latin and published translations of Virgil and Homer. At the Restoration, Charles II entrusted him with “the poetical part” of the coronation. Back in Ireland, Ogilby opened another theatre but subsequently settled in London.

After the Great Fire of 1666, he surveyed disputed London property. He set up as a printer with the title of “king's cosmographer and geographical printer” and produced many volumes notable for their typography and illustrations. His Britannia . . . a Geographical and Historical Description of the Principal Roads thereof . . . , published in 1675, was part of a projected world atlas and a landmark in accurate road description.