Why do some people pronounce the first part of "Halloween" like the word "hollow"?
In Old English, the word we know today as "holy" was halig, pronounced HALLY. In the Middle Ages, the pronunciation started to shift from HALLY to HOLLY. We see this phenomenon in the word "holiday" (literally a "holy day"), where the original Old English pronunciation survives in the family name "Halliday", originally given to people born on a holy day.
Subsequently HOLLY shifted even further to HOLEY. But in the word "hallow" (originally meaning "saint"), the final shift to HOLE never happened, leaving us with the two older pronunciations: HALLOW and HOLLOW.
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