Understanding Middle English
If you have no experience at reading Middle English, the primary obstacle to appreciating the General Prologue is the language itself. Chaucer's English is over 600 years old, but it is still recognizably English, and with a little effort it can be understood. In fact, one of the great benefits of reading Chaucer is learning this older form of English, one that allows us insight into the minds and lives of the people who spoke it. At first the going is slow, and the language is full of words and phrasing that are at best unusual, at worst incomprehensible. Accordingly, on this site difficult words are glossed, that is, translations for them will pop up in a text box when you place the cursor over them. There is also a modern English translation, so if the Middle English text--even with the glosses--still leaves questions of comprehensibility, you may want to consult it. As you progress through the General Prologue, the translation should become unnecessary, and by the time you are finished, you will have enough familiarity with the language that it will be easier to understand, and its rhythms and manners of expression more comprehensible.
A useful first approach is to read a portion of the General Prologue with full use of the glosses, noting what the words mean, how they are used, and how expressions are formed, and, then, after this first reading, to read the same portion again without the glosses. This uninterrupted second time through will give you a better sense of the overall meaning and the flow of the language.
Pronouncing Middle English
Listening to the language as it was spoken also helps, since pronunciation is important to understanding as well as to appreciating Chaucer's rhymes and rhythms. As with the words and phrasing, pronunciation of English has also undergone major changes since Chaucer's day. For well over the past century, scholars have been determining the sounds of Middle English, and today there is general agreement about its pronunciation (although some small points are still disputed). To hear renditions of it, click on the sound icons in the right-hand margins of the text or on Sounds in the left framebar, which will take you to the Chaucer MetaPage's audio collection of Chaucer readings. All of these have been made by professors who specialize in Middle English studies and are familiar with the language. These should be especially helpful if you want to get a feel for the language and its pronunciation by learning to recite the opening lines (lines 1-18) or other passages.
For Further Study
For a presentation of the finer points of pronunciation and an introduction to the grammar, consult Elizabeth Rehfeld's Chaucer's Pronunciation, Grammar, Vocabulary on the Harvard Geoffrey Chaucer site.
For a discussion of the status and use of English in Chaucer's lifetime, see Larry Benson's The English Language in the Fourteenth Century, also a part of the Harvard Chaucer site. Quoting extensively from contemporary sources, Benson traces the use of French and English from the time of the conquest to Chaucer's day, when English once again re-emerged as the primary language of England. He also provides information about the English dialects (with examples) as well as the Great Vowel Shift.
For learning more about individual words, use Benson's Glossarial DataBase of Middle English, accessed via the University of Michigan. This database provides all the occurrences of any word in The Canterbury Tales along with its part of speech--and at a click will give the line of poetry for each occurrence. For instructions on using the Glossarial Database, click here.