Penn attended Chigwell Grammar School.

Oliver Cromwell soon closed Parliament and became Lord Protector of England. Due to the political climate, Admiral Penn moved his family to their estates at Macroom Castle, Ireland.

The English Civil War
Since King Henry VIII broke from the Catholic Church and formed the Church of England, the English people had been embroiled in a conflict over religion. The break with Rome had opened a floodgate of religious arguments which would lead to new protestant sects and a struggle for power. At this time, there was NO separation between church and state, which meant that the church in charge would have far-reaching influence over the entire country. After over a century of struggling, it came down to the supporters of Charles I and his Church of England against the elected Parliament, which consisted of mainly Puritan members. In 1642 war broke out, and finally ended in 1646 with the surrender of Charles I. Charles was beheaded three years later and the Puritans took control, declaring England a Commonwealth and controlling the government for the next decade.

Penn heard his first Quaker preacher, Thomas Lee.