Whenever you find yourself teaching early literature, there is one difficulty you will ALWAYS face: alienation. In Chaucer's case, we have a double whammy: 1) He is old and "boring"; 2) This is English?! If the antiquity and the strangeness of the language weren't enough, Chaucer spends his time hanging around with Pardoners and Summoners and Manciples. Who ARE these people anyway? For students weaned on Magic Treehouse-type books – in which one can travel seamlessly through time and not have any version of culture shock – this kind of text is hard to take.
This means that you have to be an ambassador of the space-time continuum for your students. Yes, Chaucer might have been a stodgy white guy who spent all his time trying to curry favor with the current Alpha-Dynasty, but he knew a good narrative frame when he saw it. Make the connection: pilgrimage = road trip. How many cult classic films have exactly the same concept at their roots?
Use the links provided in this guide to learn more about the importance of pilgrimage as both a social and religious practice. People didn't just go to erase a big sin. They went to chat and sing along the way. They went to hook up (just look at the Wife of Bath). They went to scam fellow pilgrims (like the Pardoner and the Summoner). The simple fact is this: times do change, but people often don't. We all have wanderlust and we all can understand the pleasure to be had on a road trip complete with naughty stories.