As evidence that some things never change, here are two postcards, roughly 15 years apart, showing artists painting Rockport’s picturesque harbor from above it on The Headlands. One is just as likely to encounter the same scene today (in warmer weather, that is).
The top postcard bears the caption, “Rockport, Massachusetts, One of the Art Towns of America.” It was published by the Rockport Photo Bureau. There is no date, but markings on the reverse and the people who are pictured lead me to estimate that the picture was taken around 1930.
The bottom postcard is by Virginia Cleaves Little, who was the daughter of Charles Cleaves, the founder of the Rockport Photo Bureau. This image is marked with a 1945 copyright, so we know its date for certain.
The name of The Headlands is attributed to explorer John Smith, who was commissioned by King James I of England in 1614 to chart the coast of Maine and Massachusetts. He gave it the name “Ye Faire Headlands.”
In 1772, Caleb Norwood bought the land and it was often thereafter referred to as Norwood’s Head.