This one feels like cheating! Although there are 33 named islands in the county there are only 7 towns. The county was named for James, Duke of York. (He had 10,000 men.)

Aquinnah
Pronunciation: Uh-kwin-uh
Population in 2020: 439
Incorporated: 1870 (as Gay Head)
Original name: Aquinnah
Aquinnah (“land under the hill”) is the Wampanoag name for the area of Martha’s Vineyard the English called Gay Head. The name was changed in 1997 by popular vote. This is the only town in the Commonwealth that has reverted to its indigenous name, as far as I know.
Chilmark
Pronunciation: Oke Bluffs
Population in 2020: 1,212
Incorporated: 1694
Original name: Nashawahkamuk (“between the land”)
After breaking away from Tisbury and Edgartown, English settlers named their new town after Chilmark, England, ancestral home of missionary Thomas Mayhew, who eventually tried to start a feudal society with a hereditary monarchy on Martha’s Vineyard. More about this fellow here.
Edgartown
Pronunciation: As it looks but it’s “town” not “ton”
Population in 2020: 5,168
Incorporated: 1671
Original name: Nunnepog
Edgar Stuart was the young son of James II of England, Ireland and Scotland (at the time Duke of York). Edgar unfortunately passed away in 1671 at the age of 3. The town was named for him before the colonists received word of his passing.
Gosnold
Pronunciation: Goz-nold
Population in 2020: 70 (This is the least populated town in Massachusetts.)
Incorporated: 1864
Original name: unsure
Ooh, ooh, I know this one! Gosnold was named for English explorer Bartholemew Gosnold, right?
Yes, Amy, you clever thing, it was.
Oak Bluffs
Pronunciation: Oke Bluffs
Population in 2020: 5,341
Incorporated: 1880 (as Cottage City) 1907 (as Oak Bluffs)
Original name: Ogkeshkuppe
Oak Bluffs is named for the oak trees on the bluffs overlooking Nantucket Sound.
I like Cottage City better.
Tisbury
Pronunciation: Tiz-burry
Population in 2020: 4,815
Incorporated: 1671
Original name: Nobnocket (for Vineyard Haven, a part of Tisbury)
Tisbury is named for Tisbury, England, the home of self-styled Governor Thomas Mayhew (see above). Hey, wait a minute…wasn’t Chilmark named for Mayhew’s home back in England? Tisbury claims him, but Chilmark is also home to Mayhews, so IDK.
West Tisbury
Pronunciation: West Tiz-burry
Population in 2020: 3,555
Incorporated: 1892
Original name: Taacame
West Tisbury split from Tisbury but took the site of the original settlement, which was once called Middletown.
And there you have it! Essex is next. Brace yourself.
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