There are 14 counties, with 39 cities and 312 towns.
Generally speaking, New England states do not have as active a county government system as compared to the rest of the nation. For the most part citizens engage directly with a state office not a county office. Example, in Massachusetts state roads, usually numbered routes are cared for by MassDOT, Highway Division, while individual communities care for the non-state roads within their borders. Additionally, many counties have been abolished in as much as there is no separate county budget paying for the county offices. Though all counties still remain, the offices of the abolished counties have been administratively placed under certain state Secretariats. The Registrars of Deeds in abolished counties are still elected by those in their county whereas the budget is administered by the Secretary of the Commonwealth’s office. Likewise Sheriffs continue to be elected within their counties and they along with county houses of corrections have been administratively placed under the Executive Office of Public Safety.
Abolished County Governments:
Berkshire, Essex, Franklin, Hampden, Hampshire, Middlesex, First Norfolk, Suffolk and Worcester.
Intact County Governments:
Barnstable, Bristol, Dukes, Nantucket, Second Norfolk and Plymouth.
A Listing of Cities and Towns, the Counties they are in with the Dates of Settlement, Incorporation as a Town and, if applicable, as a City
Historical data relating to the incorporation and abolishment of counties in the Commonwealth of Massachusetts
How did Brookline and Cohasset become "islands" of Norfolk County?
When looking at the county boundaries, you may notice that the towns of Brookline and Cohasset lie outside and are not contiguous to the rest of their county. The second Norfolk County was organized in 1793 from parts of southern Suffolk County and the towns of Brookline+, Cohasset, Hingham and Hull as well as the approximate area of towns that now comprise Norfolk County. In 1803 the towns of Hingham and Hull opted out of Norfolk and became part of Plymouth County, thus cutting off Cohasset.
+ In 1795, Brookline petitioned the Supreme Judicial Court to "change its allegiance" back to Suffolk County, the court however, ignored the petition.
Anomalies of note: Chestnut Hill, Massachusetts 02467
There are many neighborhood or area names that may cross local borders of one kind or another but, Chestnut Hill goes a little further than most. It is comprised of parts of the City of Boston, the City of Newton, and the Town of Brookline, as well as being comprise of the counties Suffolk, Middlesex, and Norfolk.