The area that is now Gloucester, MA, was inhabited briefly by European settlers around 1626. The settlement was abandoned, but people returned slowly, and the town was founded as Gloucester in 1642, taking its name from a city in South-West England.
Gloucester shares the Cape Ann peninsula with Rockport, and both communities became important fishing ports due to their proximity to Georges Bank. Rockport was set aside from Gloucester and incorporated in 1843.
Stories from Gloucester
The Reluctant Pirate from Ipswich, Captain John Fillmore - John Fillmore of Ipswich was taken prisoner in 1723 by the pirate Captain Phillips. After many months he and three other prisoners overcame their captors, seized command and sailed the ship into Boston. "Captain" John Fillmore became a legend in his own time.… Continue reading The Reluctant Pirate from Ipswich, Captain John Fillmore 
The Grand Hotels of Gloucester and Cape Ann - 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.… Continue reading The Grand Hotels of Gloucester and Cape Ann 
Wreck of the Hesperus, Dec. 15, 1839 - "It was the schooner Hesperus,
That sailed the wintry sea;
And the skipper had taken his little daughtèr, To bear him company."… Continue reading Wreck of the Hesperus, Dec. 15, 1839 
The Cape Ann Sea Serpent - The earliest recorded sighting of a Sea Serpent in North American waters was at Cape Ann in 1639. In 1817, reports spread throughout New England of a sea serpent sighted in Gloucester Harbor.… Continue reading The Cape Ann Sea Serpent 
The Battle of Gloucester, August 8, 1775 - Royal Navy Captain John Linzee commanding the sloop-of-war HMS Falcon, chased a scooner into Gloucester Harbor, upon which the townspeople responded with their militia. Linzee failed in his attempt to retaliate by burning the town, and the patriot forces captured three dozen British seaman.… Continue reading The Battle of Gloucester, August 8, 1775 
The Cape Ann Earthquake, November 18, 1755 - At between 6.0 and 6.3 on the Richter scale, the 1755 Cape Ann Earthquake remains the largest earthquake in the history of Massachusetts, and caused great alarm. … Continue reading The Cape Ann Earthquake, November 18, 1755 
Sketches of Cape Ann - Charcoal sketches From "Gloucester and Cape Ann" by S. G. W. Benjamin, Harper's New Monthly Magazine, September 1875… Continue reading Sketches of Cape Ann 
Awful Calamities: the Shipwrecks of December, 1839 - Three gales of unequaled fury and destructiveness swept along our coast carrying desolation and death in their stormy pathway, and overwhelming many families in the deepest mourning.… Continue reading Awful Calamities: the Shipwrecks of December, 1839 
Peg Wesson, the Gloucester Witch - An old legend about the Gloucester witch Peg Wesson is often mentioned, but never was it told in such detail as in this story published in the Boston Evening Transcript, October 14, 1892. It was carried in papers throughout the country.… Continue reading Peg Wesson, the Gloucester Witch 
A Tragic Story from Old Gloucester - In 1821, the Annisquam woods was the scene of a murder. A youth, Gorham Parsons, while chopping wood, struck and instantly killed a boy of 10 years, named Eben Davis with a hatchet.… Continue reading A Tragic Story from Old Gloucester 
The Spectre Leaguers, July 1692 - In the midst of witchcraft accusations in 1692, Gloucester was invaded by a spectral company for a fortnight. Their speech was in an unknown tongue, and bullets passed right through them. … Continue reading The Spectre Leaguers, July 1692 
Dogtown, its History and Legends - Dogtown is a five square mile area of Gloucester and Rockport strewn with glacial boulders. Visitors to Dogtown find cellar holes of abandoned houses, and boulders emblazoned with inspirational messages. … Continue reading Dogtown, its History and Legends Stories from Rockport
Wreck of the Watch and Wait, August 24, 1635 - Many ships and lives were lost in the Great Colonial Hurricane, including 21 passengers who had set out from Ipswich on August 21, 1635 on a small bark named "Watch and Wait." As they rounded Cape Ann they were suddenly met by the force of the winds.… Continue reading Wreck of the Watch and Wait, August 24, 1635 
Murderer in Rockport - On May 21, 1932, Rudolph Oker went to his father's Rockport shop and found him on the floor in a pool of blood with his skull cracked open. Arthur Oker's safe and his pockets had been emptied.… Continue reading Murderer in Rockport 
The British Attack on Sandy Bay, Sept. 8, 1814 - Rockport experienced one of the oddest invasions in U.S. history during the War of 1812 when the town's fearless residents stopped the British with rocks and anything they could get their hands on.… Continue reading The British Attack on Sandy Bay, Sept. 8, 1814 Sketches of Cape Ann - Charcoal sketches From "Gloucester and Cape Ann" by S. G. W. Benjamin, Harper's New Monthly Magazine, September 1875… Continue reading Sketches of Cape Ann Awful Calamities: the Shipwrecks of December, 1839 - Three gales of unequaled fury and destructiveness swept along our coast carrying desolation and death in their stormy pathway, and overwhelming many families in the deepest mourning.… Continue reading Awful Calamities: the Shipwrecks of December, 1839 
Killed by a Swordfish in Ipswich Bay, August 19, 1886 - Captain Franklin D. Langsford sailed from Cape Ann in pursuit of swordfish. After harpooning one in Ipswich Bay, the fish turned and thrust its sword through the boat and the Captain. Not yet realizing that he was wounded, he seized the sword and exclaimed, "We got him anyway!"… Continue reading Killed by a Swordfish in Ipswich Bay, August 19, 1886 
Hannah Jumper leads raid on Rockport liquor establishments, July 8, 1856 - On the morning of July 8, 1856, two hundred women, three men and their supporters gathered in Rockport's Dock Square and unfurled a banner with a black hatchet, determined to destroy all the alcohol in the town. The leaders of the mob was a 75-year-old seamstress named Hannah Jumper.… Continue reading Hannah Jumper leads raid on Rockport liquor establishments, July 8, 1856 
Gloucester and Rockport (MA) (Images of America)
Historic Ipswich 