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.”
“The Fairview is located at East Gloucester on elevated ground overlooking the waters of picturesque Gloucester Harbor”
“The Brynmere is located at Annisquam at a point where the River meets the open sea, where a fine view of Annisquam River, Coffin’s Beach and the sea, may be obtained.”
The Oceanside Hotel, Gloucester MA, circa 1900.
“The Oceanside is located at Magnolia, Mass., within a few minutes’ walk of Magnolia Beach and the open Ocean.
The Pavillion Beach Hotel
The Surfside Hotel, formerly Pavilion Hotel
“The Surfside is located on Western Avenue, Gloucester, directly on the ocean front.”
Colonial Arms: Built 1904 – by George Stacy, End of Niles Beach. 300 rooms – booked solidly for 4 seasons Burnt New Year’s Eve 1908, Beauport was being built next door – possible sparks from chimney started fire
Moorland Hotel at Bass Rocks
“The Moorland is located at Bass Rocks within a short distance of Good Harbor Beach and directly on the broad Atlantic.”
“The Aborn Hotel and Cottages are located at Magnolia, Mass., within a very short distance from the Ocean and within a hundred yards of the famous Kettle Rocks.”
“The Grand View is located on high land on Annisquam Point commanding a splendid view of Annisquam River and Ipswich Bay.”
The Hawthorne Inn
“The Hawthorne Inn’and Cottages are located at East Gloucester on the Harbor’s edge, affording a most picturesque view of Gloucester Harbor.”
“The Beachcroft is located at Eastern Point within a stone’s throw of a beautiful bathing beach.”
“The Edgecliffe is located at High Rocks, near Long Beach, right on the Atlantic Ocean, offering splendid opportunities for fishing and surf bathing.”
The Hesperus Hotel in Magnolia
“The Hesperus is located at Magnolia, Mass., within a short distance of Magnolia Beach and the open sea.”
“The Thorwald is located at Bass Rocks, two hundred yards from Good Harbor Beach with its splendid surf bathing.”
“The Overlook is located at Annisquam on a commanding eminence offering a beautiful view of the waters of Annisquam River and the surrounding country.”
The Harbor View Hotel was on Wonson Cove in East Gloucester. The large hotel was home to many summer artists, including Gordon Grant and Tom O’Hara (bellhop in the 20’s
The Rockaway House was built in 1896 on the homestead estate of William Rackliffe. This summer hotel was managed by Rackliffe’s son-in-law, Captain Frank Foster. Built on what Rocky Neckers once called “Scandal Hill,” The Rockaway House is one of the rare hotel buildings from this period still standing in Gloucester but has been significantly altered. See the comments below.
The Chicataubut Inn on Long Beach, as it appears today
The Chicataubut Inn on Long Beach, circa 1900