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.
The rule here is simple: ignore the "ce," ignore the "r" in the middle, and squash the whole thing together. It rhymes with "rooster" (if the rooster had a Boston accent). The "shire" in the sauce (Worcestershire) is a whole other debate, but for the city itself, just think of a "wuss" and add "ter."
The Runner-Up: Leominster
Correct Pronunciation: LEM-ster
This is the ultimate trap for people who passed second-grade reading. You see "Leo," you say "Leo." It makes sense. It is logical. It is wrong.
In this central Massachusetts city, the "o" is purely decorative. You do not say "Leo-minster." You say LEM-ster, rhyming with "hamster." It is believed this pronunciation drifted over from the original town in Herefordshire, England, and the locals have fiercely defended the dropped vowels ever since.
The "Alphabet Soup" Hall of Fame
While the top two are famous for dropping syllables, the rest of the state is famous for just being confusing.
1. Leicester
Correct Pronunciation: LESS-ter. Just like its cousin Worcester, this town decides that the "ice" in the middle is irrelevant. It is not "Lie-chester" or "Lee-sess-ter." It is LESS-ter. Short, punchy, and confusing to anyone looking at a map.
2. Scituate
Correct Pronunciation: SIT-choo-it (or SIT-u-it.) This coastal town’s name comes from the Wampanoag term satuit, meaning "cold brook." Visitors often try "Skite-u-ate" or "Sit-u-ate," but the local flow is a quick SIT-choo-it. It sounds like you are sneezing in slow motion.
3. Billerica
Correct Pronunciation: Bill-RICA This one breaks brains because it looks like a girl’s name (Erica) is hiding inside. It is not "Bill-Erica." The locals delete the 'e' entirely. It rhymes with "brick-a." Bill-RICA.
4. Peabody
Correct Pronunciation: PEE-buh-de.e You have a body. This town does not. It is not "Pea-BODY." The second syllable is a schwa sound (a soft 'uh'), and the final syllable is quick. PEE-buh-dee. If you say "body," everyone knows you are a tourist.
The "Tribal Trouble" Section: Cochituate
Correct Pronunciation: Koh-CHIT-choo-it. A village in Wayland, this Native American name is a nightmare for news anchors. It looks like a chemistry experiment. The trick is the rhythm: Koh-CHIT-choo-it. It is fun to say once you get it, but getting there requires a lot of trial and error.
The Verdict
In Massachusetts, letters are merely suggestions. The 'r's disappear, the vowels shift, and syllables vanish into thin air. It is a history lesson in efficiency: why say three syllables when one will do? So, if you are visiting the Heart of the Commonwealth, remember: You are not in War-chest-er. You are in Wuss-tah.
For a comprehensive audio guide to these and other local tongue twisters, you might find this video helpful: Pronouncing Massachusetts Cities & Towns!. This video is relevant because it features a local breaking down the correct pronunciations of many towns mentioned in this article, including the notoriously difficult Peabody and Worcester.