Compare this view of Main Street — which I estimate to be 1915 — with this one from 1911 and this one from 1920, all from more or less the same angle. Also compare it with this one from 1906 looking in the opposite direction and this one from 1911 of Memorial Hall near where these were taken.
In the one above, the brick building to the left has a sign that identifies it as Rockport National Bank — pretty much across the street from where it is now. In the 1920 card, the same building is the third down on the left.
Neither this card nor the 1920 card was dated (the other two were). I estimated the date of the 1920 card based on the appearance of the cars. The more I look at cars from that era, the more I realize that the car in that picture could have been made anywhere from 1910 to 1920.
The picture above provides an additional clue. I can just make out the license plate. It is white lettering on a dark background. It appears that “Mass.” is imprinted vertically to the left side of the plate, followed by the numbers “8677.”
Much to my surprise, the Registry of Motor Vehicles has a web page devoted to the history of Massachusetts license plates. Unfortunately, none of the plates pictured or described there matches this one. Further searching on Google, led me to eBay, where — who knew? — there is an ample market in antique license plates. Even there, I could not find an exact match. But putting information from the RMV site together with clues from the eBay images, it seems safe to date this license plate at around 1914 or 1915.
This card was published by Thomson & Thomson, Boston, Mass. It was printed in France.