A Visual Guide
With towns that end with "bury," we will either say it as it looks or we change it to berry. There are written rules as to designation. Tewksbury is one of the berry towns. Reading is a funny one. It's such a simple word, as a verb anyway. Technically, it's a heteronym, as once it is used as a name of a town in Massachusetts it sounds very different.
We don't just omit "r" from words, we also simply ignore other letters when it suits us. In Peabody, an odd name for sure, but one that seems straightforward. Nah, we have removed the "o" for a reason I cannot explain. With Norfolk, another that appears easy enough, we have again changed how it sounds from the given letters. We replace the letter "l" with an "r." Sometimes, and this usually depends on your local neighborhood, it can be said Nor-fik. It just depends on where you grew up.
I think these are two of the funniest we have. They are absolutely nothing like spelling would presume. Leominster, a compound word similar to Barstable that appears very simple. I don't have any idea if it was ever pronounced as it looks. I have never heard Leicester said correctly by a non-local. I've heard it as lee-i-sester and li-kester often. Completely understandable. Who would assume it's just a fancy way to say Lester?
I love hearing strangers pronounce Billerica. Why do we leave out the "e"? It's anybody's guess. Ayer is usually said as a two-syllable word, but not by locals. We don't do this to deliberately mess with people. It's just one of those things.
Glouster is world-famous for it's history, the popularity of the book and movie The Perfect Storm, and for the importance of the town to the fishing history. Yet, it still is hardly ever said as locals say it. Glow-ster and Glo-ust-er are common mistakes. Carver, another historical town, is most often said in a typical Boston/New England way of changing the "r" to various tones of "a." There is a very popular hotel and spa in Plymouth called The John Carver Inn. When we say the name of this place, for some reason, it actually sounds like car-ver, just like it's spelled. Go figure.