Why is Newfoundland pronounced 'Newfindland'?

It is not pronounced as Newfindland. There is just a reduction in the vowel quality, so the /aʊ/ diphthong is reduced to the schwa [ə]. This can lead to the impression in perceiving you described. read more

People in Saskatchewan (where I am) pronounce it New-Found-Land. However newfies pronounce it New-Fund-L'nd. This is partially because its full of drunk irish/scottish inbreds (j/k). Seriously, its pronounced differently there because of their accents. You'll also notice everyone there pronounce their "r"'s really hard (k-air instead of car). read more