Cresswell was the son of a landowner and sheep farmer in Crowden-le-Booth, Edale, Derbyshire. At the age of 24 he sailed to the American colonies after becoming acquainted with a native of Edale who was now resident in Alexandria, Virginia. For the next three years he kept a journal of his experiences, along with comments on political issues. He became unpopular due to his opposition to the independence cause in the American War of Independence. Cresswell returned to England, and after a failed attempt to receive a commission from the ex-governor of Virginia, John Murray, 4th Earl of Dunmore, he returned to Edale to resume farming. He died in Idridgehay in 1804.
He wrote a journal while he was in the Americas. He recorded most of his time alive. Now the journal is very famous