Does Chaucer include examples of each of the estates in his "General Prologue"? List at least one pilgrim for each of these categories with a short description of the qualities each represents. Can you further divide representatives of the Clergy as either regular or secular clergy (see Norton Topics overview (Links to an external site.)Links to an external site.)? Which pilgrims do not fit neatly into any of the traditional estates? Why?

The term "estate" in Medieval times referred to a particular social group. Unlike modern society, the various social classes were highly stratified; one’s estate was largely fixed at birth, with a few exceptions.
In the “General Prologue,” Chaucer discusses the pilgrims at the Tabard, many of whom are clear examples of each estate. These estates include the church, nobility, and peasantry. Within each of these estates, Chaucer lists multiple pilgrims. The Friar is an example of the Church, and the narrator describes him as greedily accepting donations for his order while ignoring the poor. The Friar is supposed to represent the greedy, hypocritical faction within the church. The Knight is the first pilgrim described and an example of the nobility. The Knight is a near-perfect individual, who behaves chivalrously and is kind, implying that he represents the ideal nobleman who is good to those beneath him on the social ladder. The Miller is an example of the peasantry, and he represents the uncouth, dumb brute. The Miller is proud of his pointless feats of physical strength, and he loves perverted jokes. He is an example of the uneducated, immoral members of the lower classes.
One could certainly argue that the Pardoner and the Summoner are secular members of the clergy, since they view the church as a means of income. Both of these characters use religious power as a way to improve their status within the community and line their pockets, but neither is portrayed as particularly pious. In fact, I think both the Pardoner and Summoner answer the third part of your question. They don’t really fit into the Church estate, because the Church, as the narrator points out, generally disapproves of them. They are also disliked among the pilgrims, albeit particularly by the narrator.
One could also argue that members of the emerging middle class at the time don’t fit into one of the three estates. An example of this is the Merchant. The Merchant certainly isn’t a part of the nobility or church, but he also seems to rank above a mere peasant. Despite being in debt, the Merchant portrays himself as wealthy, with his frequent talk of investments and his fashionable clothing. This indicates that the Merchant is somewhere in the middle (hence middle-class). Other pilgrims that do not fit, for similar reasons, neatly into one estate include the Physician, the Man of Law, and the Franklin. Each of these pilgrims, the Merchant included, is focused on wealth acquisition and increasing his social status.