It was on April 17, 1387 that Chaucer's pilgrims set out on the road to Canterbury. Chaucer worked most of his life as a bureaucrat, but was also a soldier, a student of law, a traveler, a functionary in the royal court and sometime diplomat, a carrier of messages.
When he was 16 he was captured by the French at the Battle of Rheims and was ransomed by Edward III for £16. We know this for certain, perhaps because kings kept receipts.
He was 44 when he began writing the tales told by the pilgrims on the road to Canterbury. Ten years later, on April 17, 1397, he read the stories out for the first time at the court of Richard II, becoming, at age 54, the first real star performer in English literature.