This one has me stumped. The title is “The Willow Walk.” I know that Gloucester and Rockport had many fine willow groves, most notably the Annisquam Willows. But I can find no reference to anything in Rockport with the formal name, The Willow Walk. As a guess, I would say this is Pigeon Hill. If any reader has more information, please share it.
Compare this picture to this one by Charles Cleaves. Both show people strolling down a hill and have somewhat similar vantage points, except that there is no sign of Landmark Lane in this view.
As for the date, I am guess-timating about this also. The postcard does not identify a publisher or a date and there is no postmark. However, I have several cards with identical printing on the reverse, all from roughly around 1910.
Vintage Rockport 
This looked like Halibut Point to me, and then, as I looked at it more, I thought, it just COULD be Pigeon Hill; I’m wondering if the photographer was taking the picture from the perspective of the Village Improvement Society field. ???
That field was the general vicinity I imagined this to be.