At the beginning of the 20th Century, Cape Ann was a popular destination for tourists. Gloucester’s grand hotels were the subject of “The Summer Hotel Guide,” published in 1905. Images and text are available through Archive.org:
“This little book will rejoice in the thought that it has accomplished its mission if in interesting you in Gloucester, it has added another to the long list of friends of this quaintly beautiful seaport town. If it could speak it would say to you, ” Gloucester welcomes you to her shores, and invites you to enjoy with us the delightful climate and varied attractiveness which she offers.”
To Reach Gloucester, Gloucester, Massachusetts— the place you come back to — is situated on that rugged promontory known as Cape Ann, where cooling ocean breezes blow continually from off the broad Atlantic. It is thirty miles from Boston from which it may be reached by Train, Steamer, Trolley or Automobile. About sixteen trains daily leave the North Station, Boston, via the Boston & Maine Railroad, direct for Gloucester, the Express Trains reaching Gloucester in less than an hour.
The Steamer trip on the finely equipped steamers of the Boston & Gloucester Steamboat Company is a two-hour ocean sail along the beautiful North Shore, with a varied scenic view of which there is no superior. By Trolley the trip is delightfully varied on account of the ever changing panorama of beautiful scenery of sea and shore, country and city. Only one change of cars is required between Boston and Gloucester. An Automobile Trip to Gloucester is made over a fine stretch of State Highway and Ocean Boulevard.”