How many cities are there in Massachusetts? There are a total of 512 towns and cities in the state of Massachusetts. Top 10 biggest cities by population are Boston, Worcester, Springfield, Lowell, Cambridge, New Bedford, Brockton, Quincy, Lynn, and Fall River and ten oldest cities are Plymouth, Gloucester, Salem, Lynn, Marblehead, Boston, Medford, Watertown, Ipswich, and Weymouth.