I'm going with Everett or Edgartown. Exeter would be nice, since, as everyone knows, "X" sells, but it's not a MA town (though it is a street in Boston's tony Back Bay).

If it's Lowell, expect it to cause problems.

Hey! Lay off Lowell or we'll send Mickey Ward to teach you some manners!
 
After Cake uses up all 210 or so town names, they'll have to go to landmarks. The Fenway version will strike out, the MBTA version won't run in winter, and the Government Center version will corrupt your registry. Oh, I could go on...
 
:)

LOL
 
I want to know what they're going to do after Z, assuming there are any towns in Massachusetts that start with Z...maybe name them after inventors (Ampere, Bell, Copernicus, da Vinci, etc.).

b=bapu?

I'm going on the record for Essex.  It's the easiest to pronounce for non locals.

Clearly Everett.   But Easton has a nice sound too.

Ipswich.
 
Rocky

How about North Station? where you catch the train ta Maine...
 
Or this: BigDig - not to be confused with BitWig.

Anderton
LOL
 
I want to know what they're going to do after Z, assuming there are any towns in Massachusetts that start with Z...maybe name them after inventors (Ampere, Bell, Copernicus, da Vinci, etc.).

after Z, you have the letters Æ, Ø, Å.
Every Scandinavian knows that