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The Canterbury Tales

by Geoffrey Chaucer

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What was the prize for telling the best tale in the Canterbury Tales? A. a horse B. a dinner C. a book

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The prize for telling the best tale in Geoffrey Chaucer's The Canterbury Tales was a free dinner, paid for by all the pilgrims on their return to the inn. The innkeeper proposed this contest to make the journey more enjoyable, with each participant telling two stories on the way to Canterbury and two on the way back. The innkeeper also offered to accompany the group as a guide.

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In Geoffrey Chaucer's The Canterbury Tales, the prize for telling the best tale on their pilgrimage was a free dinner, paid for by all who are going on the journey to Canterbury. It is the Innkeeper who comes up with the idea to offer a prize. There are 29 people in the group, not including the narrator and the innkeeper. He's delighted to have so many people attending his Tabard Inn and offers the prize to thank them. He also offers to go with them on the journey.
Chaucer's tale is written in Middle English, which is difficult to read but not impossible. The form of the language that came before Middle English, called Old English, is almost indecipherable to modern readers. I have included the original Middle English text in which the innkeeper offers the prize below.
‘Lordinges,’ quod he, ‘now herkneth for the beste;
But tak it...

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not, I prey yow, in desdeyn;
This is the poynt, to speken short and pleyn,
That ech of yow, to shorte with your weye,
In this viage, shal telle tales tweye,
To Caunterbury-ward, I mene it so,
And hom-ward he shal tellen othere two,
Of aventures that whylom han bifalle.
And which of yow that bereth him best of alle,
That is to seyn, that telleth in this cas
Tales of best sentence and most solas,
Shal have a soper at our aller cost
Here in this place, sitting by this post,
Whan that we come agayn fro Caunterbury.
And for to make yow the more mery,
I wol my-selven gladly with yow ryde,
Right at myn owne cost, and be your gyde.
And who-so wol my Iugement withseye
Shal paye al that we spenden by the weye.
And if ye vouche-sauf that it be so,
Tel me anon, with-outen wordes mo,
And I wol erly shape me therfore.’
To paraphrase, the innkeeper says: travelers, listen to my proposal. I propose that each one of you tell two stories on the way to Canterbury to help pass the time, and then two stories on the way back. Whoever has the most interesting or funny story will win a free dinner paid for by all of us. I will be the judge of who wins. I will also come with you as a guide and pay my own way. Whoever questions my judgment as the judge can pay for everybody's trip. If that sounds good to you, I'll go get my things.
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The answer is B.

The pilgrims all meet at an inn in London before they go to make their way to Canterbury to worship at the shrine of Thomas a Becket.  The owner of the inn is going to be going along also.  He proposes a contest to help pass the time.  He says that they will each tell tales.  They will each tell two on the way down and then two more on the way back.  Whoever tells the best one gets a free dinner at the inn when they return.

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