The Kings Highway: Massachusetts’ Oldest Road Connecting Boston To New York

We all drive these roads every day here in Massachusetts, and we have to admit we’re always complaining about potholes or asking, ‘Fix the streets,’ or ‘When are the roads going to be fixed?’ Although this topic isn’t directly about potholes, it’s mainly about aging roads.

What is the oldest road in the Bay State?

According to Onlyinyourstate.com, the feature is called The King’s Highway, established by King Charles II in 1650 and gradually expanded southward from Boston until 1735. At the time, the road was a key route for mail delivery between New York City and Boston, as horse-drawn carriages were the only means of transportation.

How long is the King’s Highway?

The King’s Highway is 1,300 miles long. It begins in Boston and Cambridge and extends to New Haven and Fairfield.

Where the King’s Highway starts

From there, you can take the highway to New York, New Jersey, Delaware, Maryland, Virginia, North Carolina, and South Carolina. You might be thinking, “This all sounds familiar.” But no, it’s not Interstate 95 either.

The King’s Highway connects to the two longest U.S. Routes: Route 1 runs north and south, and Route 20 runs east and west. So, there you have it: the oldest highway is right here in the Commonwealth of Massachusetts, and you probably drive it every day without realizing it…

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