Two of the Oldest Towns in America Are in New England, but Not Where You Think (2024)

I recently booked a trip to St. Augustine, Florida, for a winter getaway, knowing it is the oldest town in America. This made me question where our New England towns are on the list of oldest in the country.

We would think Boston would be near the top, but Boston wasn't founded until 1630, long after St. Augustine in 1565.

While there's no question Jamestown, Virginia, is the second oldest town in America, it get wonky after that. However, there has consistently been two towns in New England that consistently make the list of "oldest in America".

Before Boston was incorporated, two south shore Massachusetts settlements established themselves as towns. According to thoughtco.com, the oldest town in New England is Plymouth, Massachusetts, established in 1620. This is of course when the Pilgrims landed in North America for religious freedoms. We all know the story of Plymouth Rock.

There's also Weymouth, Massachusetts, incorporated in 1622, and then Quincy, Massachusetts in 1625. As in Virginia, where many early settlements were founded near each other, so is true with Boston and south of the city.

Quincy, Massachusetts, is the birthplace of two presidents and another historical figure. Yes, John Adams and John Quincy Adams were born in Quincy (you can even tour the family homes), but so was John Hanco*ck, according to nimvo.com.

Side trivia: Dunkin' Donuts (now Dunkin') originated in Quincy, too, in 1948.

Imagine the settlements back in the 1600s thriving and being incorporated as officially the first towns in what would grow up to be one of the strongest nations in the world.