Dugdale was born at Shustoke, near Coleshill in Warwickshire, where his father, John Dugdale, was steward to the local landowner. As he was born, a swarm of bees flew into the garden, which some considered "a happy presage on the life of the babe." He was educated at King Henry VIII School, Coventry. In 1623 he married Margaret Huntbach (1607–81), with whom he had nineteen children. In 1625, the year after his father's death, he purchased the manor of Blyth, near Shustoke. During an enclosure dispute with a neighbour a few years later he met the Leicestershire antiquary William Burton, who acted as arbitrator. He became involved in transcribing documents and collecting church notes and met other Midlands antiquaries such as Sir Symon Archer (1581–1662) and Sir Thomas Habington. He began working with Archer on the history of Warwickshire and their research led them to the archives of public records in London. There he met Sir Christopher Hatton, Sir Henry Spelman, Sir Simonds d'Ewes and Sir Edward Dering. Hatton provided him with hospitality in Holborn and became his principal patron.