History of Gloucester, Massachusetts

Gloucester is a historic town in Massachusetts. The Cape Ann peninsula where Gloucester is located was created by glaciers about 21,000 years ago and the area has been inhabited by humans for thousands of years.

Gloucester was visited by many explorers during the early 17th century before it was settled and then abandoned by fishermen in the early 1620s and then later taken over by the Massachusetts Bay Colony.

The following is a history of Gloucester, Massachusetts:

Around 25,000 years ago:

  • The Laurentide Ice Sheet, a massive glacier that formed in Canada around 75,000 years ago, reaches New England.

Around 21,000 years ago:

  • The climate warms and the ice sheet retreats, dropping the soil, rocks and boulders it is carrying which forms the peninsula of Cape Ann and litters the landscape with boulders and rocky outcrops.


  • On July 16, French explorer Sieur de Monts explores Cape Ann.


  • In late September, De Monts returns to Cape Ann and makes landfall at Gloucester harbor which his cartographer, Samuel de Champlain, names La Beauport.


  • Captain John Smith explores and maps New England and names the Gloucester area Cape Tragabigzanda after a Turkish princess he knew. King Charles I later renames it Cape Ann in honor of his mother Queen Anne.


  • The Dorchester Company sends 14 fishermen to Cape Ann and they settle at what is now modern-day Fort Stage Park where they establish a fishing outpost.


  • The fishing outpost in Gloucester fails and Roger Conant, the leader of the colony, leads the fishermen to a placed called Naumkeag, which is modern-day Salem, where they settle.


  • In the fall, colonist Abraham Robinson sails from Plymouth Colony to Gloucester where he settles and establishes a fishing settlement.
Gloucester harbor, photographed by John S. E. Rogers, circa 19th century
Gloucester Harbor, photographed by John S. E. Rogers, circa 19th century


  • Colonists on a boat report seeing a sea monster on a rock near the coast of Cape Ann. Two of the colonists want to shoot the serpent but a Native-American on board persuades them not to because he warns that if the serpent isn’t killed outright it will attack them.


  • Gloucester is incorporated as a town in the Massachusetts Bay Colony.


  • The First Parish Burial Ground is established on Centennial Ave.


  • Dogtown, also known as the Commons Settlement, is settled by colonists.


  • The Edward Harraden House is built by colonist Edward Harraden on Leonard Street.


  • Eight militiamen from Gloucester are drafted to fight in King Philip’s War: Andrew Sargent, Joseph Clark, Joseph Somes, Joseph Allen, Jacob Davis, Vincent Davis, Thomas Kent and Hugh Howe.


  • In June, for several weeks Ebenezer Babson and many other colonists witness seeing French and Indian soldiers, wearing strange clothing and carrying mysterious “bright” guns, running around outside the garrison at night.
  • On July 14, Babson and colonist John Brown and some men from the garrison chase after six of these soldiers near the garrison. Babson shoots three of these soldiers, who fall down, but then quickly stand back up, fire at him, and run away. Babson chases one of them into a corn field, shoots him down but then can’t find the body. The men search the cornfield but can’t find the soldiers and then report hearing them, speaking an unknown language, in the nearby swamp. The men return to the garrison and continue to see the soldiers lurking near the cornfield but can’t seem to hit them with their bullets.
  • On July 17, colonists Richard Dolliver and Benjamin Ellary fire directly upon 11 soldiers in an orchard but the bullets have no effect on them and they scatter.
  • On July 18, Major Appleton of Ipswich sends 60 militiamen to Gloucester to help fight the French and Indian soldiers around the garrison. The militiamen often chase the soldiers but lose them in the swamp.
  • In late July, Babson encounters the soldiers in the woods and fires upon them a dozen times but his gun misfires each time. After determining that the soldiers are specters, the colonists decide to ignore them and they soon stop appearing.
  • In September and October, nine women from Gloucester are accused of witchcraft during the Salem Witch Trials: Esther Elwell, Margaret Prince, Elizabeth Dicer, Joan Penney, Phoebe Day, Mary Rowe, Rachel Vinson, Abigail Rowe and Rebecca Dike.


  • The town establishes its first school, which is conducted in the meeting house, and Thomas Rigg serves as the school master.


  • About the year 1700, the William Haskell House is built on Lincoln Street.
  • Around the year 1700, the Whittemore House is built on Washington Street.


  • Cotton Mather publishes his book Magnalia Christi Americana in which he includes Gloucester minister John Emerson’s account of the ghostly soldiers attacking the garrison in Gloucester in 1692.


  • The population of Gloucester is 700.


  • The first school house is built, next door to the town’s meeting house where school sessions had been held for the past 10 years.


  • The Davis-Freeman House is built by colonist Jacob Davis on Essex Ave.
Gloucester harbor from Rocky Point, photographed by John S. E. Rogers, circa 19th century
Gloucester harbor from Rocky Point, photographed by John S. E. Rogers, circa 19th century


  • The White-Ellory house is built on Washington Street, which was then the town green, for Gloucester’s first settled minister, Reverend John White.


  • The Dyke-Wheeler House is built by Richard Dyke on Wheeler Street.


  • The Babson-Alling house is built by William Alling on Washington Street.
  • The population of Dogtown is 25 families.


  • Forty-five men from Gloucester are drafted to participate in the Siege of Louisburg during King George’s War.


  • The population of Gloucester is 2,745.


  • The Sargent-Robinson house is built on Washington Street.


  • The population of Gloucester is 3,763.


  • The Cape Ann Light is built on Thatcher Island.


  • On June 17, two companies of men from Gloucester fight at the Battle of Bunker Hill in Charlestown, Mass. Five of the men, Daniel Callahan, Francis Pool, Josiah Brooks, William Parson, and Benjamin Smith, are killed in action.
  • On August 5, the HMS Falcon anchors in Squam harbor and sends a barge of 50 soldiers to capture cattle and sheep grazing on Major Peter Coffin’s farm but are repelled by Major Coffin and his militiamen who fire upon them from behind the dunes.
  • From August 6 -7, the HMS Falcon cruises around Cape Ann impressing several American sailors from various boats and vessels into service in the Royal Navy.
  • On August 8, the Battle of Gloucester takes place during which the HMS Falcon captures one American merchant ship and chases another one into Gloucester harbor where the captain grounds it on the flats near Five Pound Island. The Falcon sends three small boats of British sailors to capture the grounded ship but are fired upon by militiamen on shore and become trapped on the merchant ship. Three British sailors are killed and the others are captured by the militia. The Falcon bombards the town with its cannons, killing militiamen Benjamin Rowe and Peter Lurvey and damaging a church, and the crew attempts to set the town on fire but fail to do so.
  • On August 9, the HMS Falcon leaves Gloucester harbor.
  • The population of Gloucester is 4,945.


  • The population of Gloucester is 5,317.


  • The population of Gloucester is 5,313.


  • A wooden lighthouse, Annisquam Harbor Light, is built on Wigwam Point.


  • The Puritan House hotel is built by James Tappan and is the first brick building in Gloucester.
  • The population of Gloucester is 5,943.


  • In the winter, Dogtown resident and sheep farmer Abraham Wharf crawls under a boulder in Dogtown and dies by suicide.
  • By this time, only six of the original 60 to 80 houses in Dogtown remained.
  • In June, during the War of 1812, British raiders invade Annisquam Harbor in attempt to capture the sheep of Dogtown resident William Pearce.


  • Throughout the summer, hundreds of people, including the crews of four whaling vessels, report seeing a sea serpent in Gloucester harbor.


  • The population of Gloucester is 6,384.
General view of Gloucester, Mass, by C. A. Beckford, circa 19th century
General view of Gloucester, Mass, by C. A. Beckford, circa 19th century


  • A stone lighthouse, Ten Pound Island Light, is built on Ten Pound Island in Gloucester Harbor.


  • On January 1, the first newspaper in Gloucester, the Gloucester Telegraph, is issued.


  • On September 16, a house on Main Street, owned by Samuel Gilbert, catches fire which spreads and destroys 27 other houses and 43 stores in the downtown area.
  • The Gloucester Lyceum is established.
  • The population of Gloucester is 7,510.


  • The Eastern Point Lighthouse is built at Gloucester Harbor.


  • On August 18, the first edition of the Gloucester Democrat newspaper is published.


  • The Gloucester Democrat merges with the Salem Advertiser newspaper.


  • In February, the last resident of Dogtown, Cornelious Finson, is dragged out of one of the cellar holes and placed in a poor house in Gloucester where he dies seven days later.


  • Sometime around 1840, the Webster-Lane house is built on Main Street.
  • The population of Gloucester is 6,350.


  • The last remaining house in Dogtown, the home of fisherman Philip Priestly who lived at #11 Dogtown Road, is demolished.


  • The Annisquam Bridge is built over Lobster Cove.
  • In December, a train station is built by the Eastern Railroad, at the intersection of Railroad and Maplewood Avenues, and Gloucester is the last stop on the railroad line from Boston until 1861 when the line is extended to Rockport.


  • On October 11, the first edition of the Gloucester News is published.


  • The Fritz Lane House is built by artist Fritz Henry Lane on Harbor Loop Road.


  • The population of Gloucester is 7,786.


  • The wooden Annisquam Harbor Light House is replaced with an octagonal wooden tower lighthouse.
  • In December, the Gloucester News merges with the Gloucester Telegraph.


  • The Oak Grave Cemetery is established on Derby, Washington, and Grove Streets.


  • In September, Henry David Thoreau and a friend visit Dogtown and Gloucester during a walking tour of the North Shore.


  • A major fire breaks out and destroys much of downtown Gloucester.
  • The population of Gloucester is 10,904.


  • The Annisquam Bridge is replaced with a new wooden-pile bridge.


  • The Gloucester City Hall is built on Dale Ave.
  • The population of Gloucester is 15,389.


  • Gloucester is reincorporated as a city in the Commonwealth of Massachusetts.


  • On July 6, entrepreneur Roger Babson is born in Gloucester.


  • A weekly newspaper called the Gloucester Bulletin is established.


  • A light keeper house is built for the Eastern Point Lighthouse.


  • Artist Winslow Homer spends a year living at the light keeper’s house, with Keeper Charles Friend, at the Eastern Point Lighthouse and paints the local seascapes.
  • The population of Gloucester is 19,329.


  • The stone lighthouse on Ten Pound Island, Ten Pound Light, is replaced with a conical lighthouse made of iron.


  • The Gloucester Net and Twine Company is established on Maplewood Avenue.
  • On August 29, the first edition of the Cape Ann Breeze is published.


  • A horsecar railway, the Gloucester Street Railway, is established in the downtown area. By the turn of the century, the railway is electrified and expanded to approximately 9 miles in length.


  • On September 18, local fisherman and aspiring matador James Merry is gored to death by his pet bull in Dogtown.
  • Poet John Greenleaf Whittier publishes a poem, titled The Garrison of Cape Ann, which tells the story of the ghostly soldiers attacking the garrison in Gloucester in 1692.


  • On May 17, the Lamartine, a schooner, sinks off the coast of Gloucester.


  • On August 21, the Gloucester, Essex and Beverly Street Railway opens for operation and runs from Gloucester to Beverly along what is now route 133.


  • The octagonal wooden Annisquam Harbor Light House is replaced with a brick lighthouse.


  • On November 27, the PS Portland steamship sinks off the coast of Cape Anne during a massive blizzard known as the Portland Gale.


  • The George O. Stacy House is built on Atlantic Road for local real estate developer and hotel operator George O. Stacy.
  • The Addison Gilbert Hospital is built on Washington Street.


  • The population of Gloucester is 26,121.


  • On December 17, a schooner named the Frank A. Palmer and a schooner named the Louise B. Crary collide during a gale and sink near Gloucester.
Main Street, Gloucester, Mass, circa 1905
Main Street, Gloucester, Mass, circa 1905


  • The Beauport house, also known as the Sleeper–McCann House, Little Beauport, or Henry Davis Sleeper House, is built by Henry Davis Sleeper on Eastern Point.
  • A bronze plaque commemorating the settlement of Gloucester is installed on a boulder in Fort Stage Park.


  • The population of Gloucester is 24,398.


  • Our Lady of the Good Voyage church is built on Prospect Street.


  • In September, the Flu Epidemic of 1918 hits Gloucester and a tent hospital is established on the grounds of the Addison Gilbert Hospital to accommodate the influx of patients. Over the next seven months, the flu infects nearly 4,000 Cape Ann residents and kills more than 250.


  • The population of Gloucester is 22,947.


  • The Gloucester Fisherman’s Memorial is constructed on Stacy Boulevard.


  • Local inventor John Hays Hammond Jr begins construction on Hammond Castle on Hesperus avenue.


  • The first annual St. Peter’s Fiesta takes place.
  • Local entrepreneur Roger Babson and his cousin Gustavson Babson purchase 1,150 acres of the abandoned settlement of Dogtown.
  • Roger Babson locates and documents the sites of the original homes of the Dogtown settlement and publishes a guide to the area called Dogtown: Gloucester’s Deserted Village.


  • Roger Babson builds a 500-square foot log cabin in Dogtown in the style of the original settler’s cabins and furnishes it with Colonial furniture and artifacts.


  • During the Great Depression, Roger Babson hires unemployed stone cutters to carve inspirational quotes into the boulders in Dogtown.
  • Roger Babson donates his 1,150 acres of Dogtown to the city of Gloucester.


  • Roger Babson runs against Franklin D. Roosevelt for President of the United States.


  • On August 9, the engine of the trawler the Joffre, catches fire and the ship sinks the following day near Gloucester.


  • The Isabel Babson Memorial Library is founded by Roger Babson in honor of his ancestor, a colonial midwife named Isabel Babson.


  • In June and July, an episode of the television show Bewitched, titled “Darrin on a Pedestal,” is filmed in Gloucester. The plot centers around the character Darrin being transformed into the famous Fisherman’s Memorial statue on Stacy Boulevard. Exterior scenes are shot at the Gloucester House restaurant, the Fisherman’s Memorial and Hammond Castle.


  • From February 5-7, the Blizzard of ’78 strikes the Northeast.
  • On February 7, a Gloucester-based pilot ship, the Can Do, is lost at sea during the blizzard while on a mission to voluntarily rescue a Coast Guard ship and an oil tanker in distress.


  • On June 24, local school teacher Anne Natti is murdered by Peter Hodgkins Jr in Dogtown.
  • On June 29, Peter Hodgkins surrenders to police at the Gloucester police station. Hodgkins is later convicted of Natti’s murder.


  • From October 28 – November 2, the Perfect Storm hits the Northeast and a Gloucester-based fishing ship, the Andrea Gale, and its crew of six fishermen are lost at sea off the coast of Newfoundland.


  • In the summer, the film The Perfect Storm is filmed in Gloucester.


  • In June, the Pregnancy Pact scandal takes place at the Gloucester High School during which 7 or 8 high school students become pregnant allegedly as the result of a secret pact to get pregnant that year and raise their children together.

Benjamin F. Arrington, editor, Municipal History of Essex County in Massachusetts, Tercentenary Edition, Volume II, Lewis Historical Publishing Company, New York, 1922.
Mather, Cotton. Magnalia Christi Americana. Vol. II, S. Converse, 1820.
McAllister, Jim. “Essex County Chronicles: While Salem Was Dealing with Witches, Gloucester Had Its Ghosts.” Salem News, 14 June. 2010, salemnews.com/opinion/essex-county-chronicles-while-salem-was-dealing-with-witches-gloucester-had-its-ghosts/article_1b7b1184-d7a8-5d92-8c8e-e27ffd23bccb.html
“The History of Cape Ann.” Cape Ann Museum, capeannmuseum.org/about/history-cape-ann/
Gloucester Reconnaissance Report. Mass.gov, May 2005, mass.gov/doc/gloucester-0/download
“Cellar Holes.” City of Gloucester, gloucester-ma.gov/715/Cellar-Holes
“The Great Fire of 1830.” City of Gloucester, gloucester-ma.gov/DocumentCenter/View/250/great-fire-of-1830?bidId=
“Babson’s Boulders: A Millionaire’s Odd Dogtown Legacy.” New England Historical Society, newenglandhistoricalsociety.com/babsons-boulders-millionaires-odd-dogtown-legacy/
Laider, John. “Seaport Says Goodbye to Men Lost at Sea.” Boston Globe, 17 Nov. 1991, bostonglobe.com/metro/1991/11/17/seaport-says-goodbye-men-lost-sea/nrfQFTss6a1ENzEOtHgv2H/story.html
“Wreckage of Sunken Pilot Boat is Discovered with Fifth Body.” New York Times, 18 Feb. 1978, nytimes.com/1978/02/18/archives/wreckage-of-sunken-pilot-boat-is-discovered-with-fifth-body.html
“17 Pregnancies at a US School after girls make baby pact.” The Guardian, 21 June. 2008, theguardian.com/world/2008/jun/21/usa
“The Great New England Sea Serpents.” New England Historical Association, newenglandhistoricalsociety.com/great-new-england-sea-serpent/

About Rebecca Beatrice Brooks

Rebecca Beatrice Brooks is the author and publisher of the History of Massachusetts Blog. Rebecca is a freelance journalist and history lover who got her start in journalism working for small-town newspapers in Massachusetts and New Hampshire after she graduated from the University of New Hampshire with a B.A. in journalism. Visit this site's About page to find out more about Rebecca.

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