Every state has its share of hard-to-pronounce city names, but in a competition, it’s likely that Massachusetts would Winthrop, for Shirley. How in the Hull do you pronounce Haverhill anyway?!
Relax…this guy runs down a dozen doozies that might tangle up Yarmouth, and his descriptions are hilarious. But for what it’s Worthington, don’t talk about Athol around an out-of-stater or he might Seekonk you in the Marblehead and then you’ll need Mendon.

Source: How to properly say Massachusetts town names (with pictures) by Rowdy4324

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