On the Massachusetts North Shore
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.
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.
"It was the schooner Hesperus, That sailed the wintry sea; And the skipper had taken his little daughtèr, To bear him company."
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.
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.
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.
Charcoal sketches From "Gloucester and Cape Ann" by S. G. W. Benjamin, Harper's New Monthly Magazine, September 1875
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.
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.
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.
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.
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.
Historic Ipswich 