Very cool piece of work. Little bit weird that Springfield gets to be the other illustrated city in Massachusetts when Worcester is the second biggest city in the entire region after Boston.
Worcester likely is too close to Boston to have room for it at the chosen level of detail.
For what it’s worth, when I zoom in on Massachusetts in Apple Maps (which seems to have finer grained zoom levels than OpenStreetMap.org or maps.Google.com), the order in which cities appear is
- Boston
- Springfield
- New Bedford
- Worcester
(I’m writing this from Springfield right now)