I think good modern day additions would be the Unemployed pilgrim and the Reality TV Star. The Unemployed pilgrim could foster some interesting dialogue, especially with the CEO, Banker, or Ponzi Schemer. My students always vote in an NFL star - and he is usually hiding his performance enhancing habits.
Chaucer included pilgrims who were representative of his perception of the greatest social evil(s) of the time. Certainly CEOs and other leaders from the corporate and financial worlds would be in my choice. I'd also choose the ones who determine the product of the television, movie, and non-classical music entertainment industry; these would include writers, directors, performers, and producers.
I have not read the other answers, but what comes to mind first for me are the Jews and Christians who travel to historically and/or culturally significant sites in the Holy Lands. While Christians (as I understand it) generally travel to these places for their religious significance, Jewish travelers may be doing so for both religious and cultural reasons. Both groups are interested in the past and in the symbolic significance that each site represents to each group. It is ironic to note that while the two faiths do not have the same theological beliefs, the Holy Lands are enormously meaningful to both.
As a contemporary representative of all the groups of individuals who have been ostracized by society at one time or another for reasons that eventually cease to be an issue, the modern pilgrimage would need to include someone who is gay/lesbian/bisexual/transexual.
I'm not sure if this fits with your assignment, but consider the many pilgrimages of the Jews over history.
Jacob's journey to Egypt to be with his sons before his death.
The Exodus of the Jews from Egypt after the Ten Plagues.
The Three Pilgrimage Festivals, still celebrated by Jews worldwide today.
The mass evacuation of Jews from Libya after World War II.
The Aliyah, ritual immigration to Israel by Jews from all over the world, considered a rite of passage by many students and religious leaders.
Pilgrimage, whether purposeful or forced, has been part of the Jewish experience for all of recorded history.
I like the idea of having a Merchant Banker, but I also think you would need to have the diversity of today's globalized world represented. Perhaps a few Latino immigrants working as cleaners or maids for the CEO would be good fun. Maybe an African-American who has managed to "do-good" in spite of the inequality facing him. I also think you would have to have an environmentalist or a tree-hugging member of the granola gang.
Today, you would surely need a banker and/or a CEO. These people would play the same sort of role that the less sympathetic clerics do in Chaucer's time. He seems to be saying that these are people who are supposed to be helping the masses and yet are only looking out for themselves. This criticism could be levelled at these leaders of our economic system. I suppose, for that matter, that they could be levelled at politicians as well since they are much more directly supposed to be helping the people.
So who would the Wife of Bath be? That's one for which I'd be interested in hearing others' thoughts!
I love this project and do something similar with my students each year. We all love the final results. By the way, I make them dress in costume and read their prologue poem to the class!
As a way to subtly voice an opinion about all of the standardized testing talk in education these days, I would be a teacher -- one who is so busy handing out scantron/multiple choice tests that she never catches her breath and doesn't even get to know her student's names, only their ID numbers. She would represent that group of teachers out there who mourn the change in the profession that reduces them to do-the-test teachers for the sake of AYP. Her "sin" would be her inability or unwillingness to challenge the current direction of education.
When I thought of your question, the first thing that came to mind is the financial situation many Americans are in. There are so many people who have lost their jobs and homes, and even sometimes family members, to this recession. So much of what we thought of as crucial to our American identity is lost. This is not a small group.
I definitely think that a good example of a modern day pilgrim are the LGBT individuals (lesbian, gay, bisexual, and transgender) all over the world. I believe that they represent a different kind of pilgrim than what one may think of when they hear the word. Perhaps they are not traveling from one part of the world to another to either escape persecution, discover themselves or more about their religion, etc (though I'm sure some have) I think that a pilgrim can also be an instigator and catalyst for change in society. Today more than ever LGBT people are immersing themselves in society, finding it more accepting and comfortable with their way of life than ever before. They are also showing others that change is great, and that having so many different types of people in the world truly makes it a wonderful place.
Hope this helps!
When I was about 10 years old, I heard my granny is going on pilgrimage. She is devotee of Lord Krishna and they are going to see all holy places in India by bus. Its a tour of one month. When she returned, I found her hair have been shaved. She shaved it in JAGANNATH Temple at Puri in Orissa. She also gave up taking apple and one species of fish. There was a drastic change in her behavior, became more tolerating and spent time in reciting verses praising Krishna most of the time. I found it curious and asked her about her tour and described us minutely each and everything how she took bath in the ocean, how he preached God in temples, how much the Brahman charged, what she took for these many days, how she talked in the language of those places.
Then I came to know about the Muslims going on Hauz to Mokka. I also read the story "Two Old men" by a Russian writer. In this story two men went on pilgrimage and on the way they traveled through Little Russia where that year crops were not good and so people confronted with famine. One of them helped a family of which all the members were almost to die and the other did not wait and went on towards Jerusalem.
The man who decided to help the family stayed for a long time providing them everything to stand on their feet with his money and finally he returned home without pilgrimage. However, God blessed him for his charity rather than visiting a place of Him considered to be Holy.
Modern men visit their places of keen interest.