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Cheshire is a county in England, and in England, both the county and the cat are pronounced:

CHESH-uh

You could pronounce it:

CHESH-er

To rhyme with mesh and purr, but then you encounter the problem of the rhotic 'R'. Many accents pronounce the 'R' at the end of words; the American accent for example; but most English accents do not do this, so if you wanted to pronounce 'Cheshire' the same way as people from Cheshire (Lewis Carroll for instance) then you would pronounce it CHESH-uh.

(But never Che-shy-er)

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Q: How do you pronounce Cheshire?
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