MASSACHUSETTS – If you ask for directions in Massachusetts and pronounce every letter on the sign, you won’t get help. You are going to get laughed at. Massachusetts place names are a chaotic blend of Native American terms (often Anglicized with reckless abandon) and old British towns that the early settlers brought with them but stopped pronouncing correctly about 300 years ago.
If we have to choose a winner—the one city that trips up everyone from Hollywood actors to confused GPS systems—it is the second-largest city in New England.
The Winner: Worcester
Correct Pronunciation: WUSS-ter (or WUSS-tah if you’re feeling local)
To the uninitiated, it looks like “War-chest-er” or “Wor-sess-ter.” If you say this, the locals will look at you like you have three heads…