Welcome to Gloucester, MA, America’s Oldest Seaport located North of Boston on Cape Ann.

The first Europeans to land on Cape Ann were the French. Samuel de Champlain led an expedition in 1605 and anchored briefly. The next year, Champlain led a second expedition, entering Gloucester harbor and calling it “le beau port,” or “beautiful harbor.” The party stayed about two weeks, making maps of the area. When they ran into 200 Indians and thought them hostile, they quickly left the area. Captain John Smith sailed by Cape Ann in 1614, but did little more than give the Cape names like “Cape Tragabigzanda” that didn’t stick. Prince Charles of England finally coined the name “Cape Ann” in 1684 for his mother Queen Anne.

Many historians cite Essex County and the Gloucester area as one of the most historically significant places in America. Please enjoy the information provided below.

Fisherman at the Wheel

Gloucester’s most famous landmark, this bronze statue was sculpted by Leonard Craske in 1923. It is located on Stacey Boulevard, overlooking Gloucester Harbor. The statue of a Gloucester fisherman, dressed in oilskins and standing at the wheel of his schooner was designed in heroic size: 1 ½ scale. It is dedicated to the over 10,000 Gloucester fishermen lost at sea since the early 1600’s. The base of the statue quotes Psalm 107, “They that go down to the sea in ships.”

Howard Blackburn

Perhaps the greatest tale of a dory separated from its schooner is the story of Gloucester fisherman Howard Blackburn. On January 25, 1883, Blackburn and his dorymate Tom Welch set off from the schooner Grace L. Fears. They had no sooner left the ship than a fog set in so thick that Blackburn could hardly see Welch. When they finally saw the riding lights from the Fears, several hours had passed. A blowing gale stopped them from reaching the ship and they lay adrift in the cold overnight. Blackburn lost his mittens overboard that night while bailing out the dory. The next day Welch became delirious and froze to death. When Blackburn tried Welch’s gloves, he could not get them on his own hands. His hands were too stiff and had become frostbitten. He wrapped his fingers around the oars, so that as his hands froze, they would hold on to the oars. He began the pull for land. The oars literally rubbed the frozen flesh off his fingers, but he rowed all day. He finally made it to shore in Newfoundland a few days later. He lost most of his fingers, but survived to become a Gloucester tavern keeper and legend. The only man to cross the Atlantic alone three times in a dory in 1899, 1901, and 1903. For more information, please visit the Cape Ann Historical Museum’s website here.

Eastern Point Light

The first lighthouse was built on the current sight in 1831 and began shining on January 1, 1832. President Andrew Jackson authorized the construction of this 30 foot lighthouse. The combined cost of the lighthouse and a small keeper’s quarters was $2,450. In 1848, the original lighthouse was torn down and rebuilt. The new lighthouse was 34 feet high and had a steady red light that sailors fondly referred to as “ruby light.” An automatic foghorn was installed in 1857. In 1890, the current lighthouse was built for an outrageous $4,300. In 1897, a two-ton steam operated fog bell was installed: the only one in the world. The keeper’s house was one of the first to have all of the modern conveniences: telephone-1896, electricity-1897, running water-1901. The lighthouse became automated in 1986 and no longer needs a keeper for either the tower or the light at the end of the breakwater.

Schooner Origins

Capt. Andres Robinson was the designer and builder of the first schooner, launched in Gloucester in 1713. A bystander remarked, “See how she schoons!” (as a stone skips on water). Robinson said, “Then, a schooner let her be,” and broke a bottle of rum on her bow. Before long, most of Gloucester and Essex shipbuilding was confined to schooners. Schooners are defined as vessels with two or more masts with the mainmast the same height or taller than the foremast. The age of sail began to end (until the Lannon) when gasoline-burning engines were introduced here in 1909.

Revolutionary War – Smuggling

In part because of the tariffs the British imposed, and the blockades of American Ports, much of the trade in Gloucester was smuggling. One story is told that a schooner arrived in the inner harbor and pulled up to a wharf in the night. Everyone, including the owner, a Colonel Joseph Foster, wanted to get the cargo, much of which was illegal, unloaded that night because a customs officer from Salem was to arrive in Gloucester the next morning. The men unloaded the boat all night long, but by daybreak, the hold was still half full (or only half empty) of smuggled goods. In those days, there was a cottage where the Blynman (cut) Bridge is today. An Irishman named John M’Kean had stood guard there when there was a smallpox scare to stop all strangers on their way into Gloucester and to “fumigate them” for the good of the town. When the customs officer landed in Gloucester, M’Kean was waiting for him and marched him off to be fumigated. The officer spent the entire day in smoke and did not peer out until after dusk. By this time, all the merchandise from Foster’s schooner and was safe from detection. After the hour of danger had passed, M’Kean allowed the officer to go on his way, “thoroughly smoked and cleansed.” The officer found everything in fine shape and returned to Salem.


The Revolutionary War came all the way into Gloucester harbor. During the war, the British sloop of war Falcon sent a barge of 50 men to Coffin’s Beach in West Gloucester. Coffin and a few men repelled the barge by firing upon it from behind the sand dunes. The next day, the Falcon tried without success to seize a schooner in the harbor. Three days later, the Falcon tried to capture another schooner, but to no avail. Finally, the Falcon attacked Gloucester and tried to burn down the fish flakes at Stage Fort Park. Although they lodged a cannon ball in the First Universalist Church, they still could not win their battle, and returned to England.

Stage Fort Park

The Dorchester Company of Merchant Adventurers sent out a company of fishermen from England in 1623. They founded the Massachusetts Bay Colony. Here, they set up stages to dry the fish before it was sent back to England. The same location was later a fort. Cannons were set up in the hills to protect Gloucester’s fishing fleet from invading pirates and enemy warships during the war of 1812.

Stacey Boulevard

“The Boulevard” was completed in 1923, for Gloucester’s 300th anniversary. Before work was started on the new boulevard, there were houses on the water side of the street. Some of them were moved across the street and put onto land that was formerly neighbors’ yards. If you take a stroll on the boulevard, take a look at the houses and notice how close they are together. Today, the boulevard is home to Gloucester’s most famous monuments including the Fisherman at the Wheel as well as the new Fisherman’s Wives Memorial (seen here). Recently, in 2006, Michael Linquata chaired a group of veterans who fundraised money for and erected a Memorial to Gloucester’s WWII Veterans. Visit their website at www.gloucesterww2vetsmemorial.org or simply visit their beautiful site on Stacy Boulevard!

The Cut

The Blynman Bridge, or the “Cut Bridge” is named for Reverend Blynman, the political and religious leader of the time. Rev. Blynman supervised the cutting of the first canal at the harbor end of the Annisquam River. The first bridge was built on this location so that fishing boats would have a safer passage home if they fished north of Gloucester. Now it is the source of long delays to summertime motorists who must wait for boat traffic to pass under the draw bridge. Annisquam is the Indian word for “river with two mouths.”

Ten Pound Island

Where did the name come from? Option 1: Early settlers bought the island from the Indians for ten British pounds. Option 2: In the early days, the settlers let sheep graze on the island. There was room for 10 paddocks or ‘pounds’ on the island. Nobody knows the real story for sure, but both seem reasonable.

Ten Pound Island Lighthouse: 1881. Once a center of Coast Guard activity and known as “Base 7,” there were seaplanes based on the island that were used for search and rescue operations. Most of the missions flown by the Coast Guard were actually in search of the notorious and elusive “rum-runners” during the days of Prohibition. One such boat, known as the “Black Duck” was known for its rum-running. Often the Coast Guard planes would follow the “Black Duck” continuously, circling overhead until it pulled into port where police had been notified to make arrests and confiscate the liquor. After the Coast Guard vacated the island, it was used for a fish hatchery.

Winslow Homer: The great American artist was one of the island’s most famous occupants.

Dog Bar Breakwater

This granite breakwater covers a dangerous reef known as Dog Bar. The auxiliary light at the end of the wall had to be turned on nightly by the keeper by hand – often a challenging feat if seas were crashing over the breakwater. The breakwater is about ½ mile long and made up of heavy granite slabs from Rockport each weighing 12 to 13 tons. Open for the public, it is a popular spot for fishing and walking.

Hammond Castle

John Hays Hammond Jr. was a prolific inventor who worked for the U.S. military. Probably the most famous of his inventions was remote control, a technology he tested by operating “ghost ships” in the harbor and scaring local fishermen. Hammond also worked with a British scientist on the invention of radar. Rumor has it that his parents did not approve of his wife-to-be so he felt he had to build an even bigger castle than his parents owned just down the road. A gift for his wife, they moved into the castle on their wedding day. Hammond traveled throughout Europe collecting artifacts. The castle is filled with 13th, 15th, and 17th century furnishings with an amazing collection of Roman, Medieval, and Renaissance art. Hammond died in 1965. A bit of an eccentric, Hammond and his cat are buried together. He stipulated in his will that his entire burial site be surrounded by poison ivy so that no one would go near him. He did not invent the Hammond organ. The Hammond Castle is operated as a museum and is open to the public. It is definitely worth a visit.

A. Piatt Andrew

A Gloucester resident, A. Piatt Andrew started the American Field Service during World War I, a few years before the Americans entered the war. Andrew’s organization used donated Ford trucks in the front lines to act as an ambulance service for wounded French and English soldiers. In appreciation, after the war, the French government presented a statue of Joan of Arc on horseback (one of three in the world) to the city of Gloucester. It stands in front of the American Legion building on Washington Street. A side note: after the war, A. Piatt Andrew went on to help start the American Legion. Post #3 is located in Gloucester. The bridge that you drive over if you come into Gloucester via Rt. 128 was named in Andrew’s honor.

Beauport Museum

Beauport is the home of Henry David Sleeper, an interior designer and collector of antiques. Each of the 40 rooms (26 are open to the public) depicts a different era of American history with appropriate antiques. Situated on Gloucester Harbor at Eastern Point, Beauport offers a fine view of the Lannon as she sails in and out of the harbor.

Revolutionary War

In the Revolutionary War, Gloucester provided 15% of the men and ships that fought for the colonies. Many left from Seven Seas Wharf, some never to return.

During the Revolutionary War, Gloucester men fought the English all over the Atlantic, from the Caribbean to the shores of France. Two companies of men from Cape Ann fought in the Battle of Bunker Hill. These were Captain Nathaniel Warner’s Company from Gloucester, and Captain Rowe’s Company from Sandy Bay (now known as Rockport).

Back to History