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Fishing boats in Gloucester harbor. Photo from gloucester-ma-gov

Fishing boats in Gloucester harbor. Photo from gloucester-ma-gov

Some terrific destinations just seem to fall through the cracks and when you finally visit, you wonder where they’ve been all your life.

My latest revelation is Gloucester, Massachusetts, a city of 30,000 about 30 miles northeast of Boston on the Atlantic Ocean.

It shares scenic Cape Ann with four other communities: Rockport, Essex, Ipswich, and Manchester-by-the-Sea, and if you like water views, boating, seafood, history, and art, you’re bound to love Gloucester and surroundings.

My wife, Catharine, and I spent a recent weekend there with old friends who live in a former sea captain’s house overlooking Gloucester harbor, where we dined on lobster as ocean breezes tempered the summer air and we watched a pink twilight settle on a parade of vessels — water shuttles, yachts, cruise ships, schooners, tour boats, party boats — passing by.

You can go whale-watching in the ocean off Gloucester, take river cruises in nearby Essex, or go sailing past the area’s six lighthouses.

With 62 miles of shoreline pockmarked with marinas and beaches it’s definitely my kind of place, but during our tours of the city I discovered just how much I hadn’t known about it. Here, then, are my top five things I didn’t know about Gloucester:

Gloucester is America’s oldest seaport.

While founded in 1623, just three years after the Pilgrims landed in Plymouth, Gloucester didn’t really get serious about seafaring until a century or so later, when vessels began to hunt the region’s rich waters for cod and other fish.

Shipbuilding has been a major industry. The fishing schooner is said to have been invented in Gloucester in 1713, and the annual late summer Schooner Festival — now in its 34th year — draws 20 schooners to a Parade of Sail through the harbor to the breakwater.

Along the harbor front walkway you can stop at Gloucester’s most iconic symbol, the Fisherman’s Memorial (or Man at the Wheel). The statue is inscribed “They that go down to the sea in ships.”

The Fisherman's Memorial "Man at the Wheel" overlooks the harbor.

The Fisherman’s Memorial “Man at the Wheel” overlooks the harbor.

But many never returned. Plaques bear the names of hundreds of fishing captains and crews lost at sea between 1716 and 2001 — among them the men aboard the Andrea Gail, which set off from Gloucester in search of swordfish in 1991 to encounter a torrential storm.

Their plight was captured in Sebastian Junger’s 1997 best-seller The Perfect Storm, followed by the George Clooney film of the same name. (Some scenes from the movie were shot in Gloucester.)

To recapture some of The Perfect Storm‘s atmosphere, stop by The Crow’s Nest bar on 334 Main Street, a fishermen’s favorite since 1972 that figured prominently in the narrative. As Junger colorfully wrote in the book, “The plate-glass window in front is said to be the biggest barroom window in town. That’s quite a distinction in a town where barroom windows are made small so that patrons don’t get thrown through them.”

While not as prevalent as in decades past, fish canneries and processing plants still line parts of Gloucester’s harbor; best known is Gorton’s of Gloucester, whose roots date to 1849. Gloucester fishermen still bring in ten of millions of pounds of seafood each year, including 16 million pounds of lobster.

On the conservation side, Gloucester is home to the Ocean Alliance, dedicated to saving whales since 1971.

(Note: St. Augustine, Florida, founded by the Spanish in 1565, could claim to be America’s oldest seaport if you count territory later acquired from Spain. And of course, Native American seaports predated the arrival of Europeans altogether.)

Neighboring Essex is the birthplace of the fried clam.

The story goes that on July 3, 1916, Chubby and Bessie Woodman were frying up some potato chips at their not-so-successful seaside food stand in Essex when someone jokingly suggested they try the same technique on clams. The following day, July 4, the Woodmans served some up to the hungry holiday crowds and the rest, as they say, is yummy fried-clam history.

Woodman's serves up fried clams and lobster. Photo from

Woodman’s serves up fried clams and lobster. Photo from

Woodman’s waterfront seafood shack (121 Main St., Essex)  is now renowned throughout New England, and you can still savor their fried clams along with lobster, chowder and other delectables — but prepare to stand in line, and grab plenty of napkins.

Gloucester is home to an American castle.

And not just any castle. This one belonged to the eccentric and brilliant inventor John Hays Hammond, who had it built in the 1920s mostly from materials he acquired in post-World War I Europe.

Now known as the Hammond Castle Museum, it took its architectural inspiration from Medieval and Renaissance Europe with added elements from ancient Italy and early America. It comes complete with moat, drawbridge, and towers.

Hammond loved to entertain there, throwing lavish dinner parties with guests including Hollywood stars such as the Barrymores and Greta Garbo and the composer George Gershwin. And he loved to play practical jokes on unsuspecting newcomers, including putting them up in a guest bedroom that, with closed doors, revealed no way out to find the bathroom.

The Hammond Castle courtyard. Photo courtesy of Hammond Castle

The Hammond Castle courtyard. Photo courtesy of Hammond Castle

Its medieval Grand Hall showcases an 8,200 pipe organ that’s the largest of its kind in a private U.S. residence, and a glass-covered courtyard where the imaginative Hammond could change the weather inside at his whim — confusing his guests by switching from sunshine to rain to fog.

You can also tour his invention room, devoted to some of his 437 cutting-edge breakthroughs in sound technology — many employed by the U.S. Navy — and more fanciful but prescient gadgets, such as what had to be the first device to shop from television by telephone, way back in 1946.

Hammond couldn’t have been too popular among his neighbors: he delighted at ringing bells from his bell tower four times an hour throughout the day and night and blasting high-decibel music across Gloucester harbor. But his castle-museum is a big draw for today’s public; it’s located at 80 Hesperus Avenue.

Gloucester is a major center for the arts.

The bohemian-style Rocky Neck Art Colony on Smith Cove is America’s oldest continually operating artists’ lair, dating from the mid-nineteenth century, and the area has attracted such artists as Winslow Homer, Childe Hassam, Edward Hopper, Mark Rothko, and pioneering painter Fitz Henry Lane, many of whose works are displayed in the Cape Ann Museum.

Neighboring Rockport has an attractive summer concert venue — the Shalin Liu Performance Center — featuring jazz, pop, and world music. (Rockport has plenty of good dining and shopping ops as well.)

The area has also been celebrated in literature. Long before The Perfect Storm came Longfellow’s epic poem The Wreck of the Hesperus, inspired by a shipwreck off Gloucester in 1839. In turn, the poem served as the basis of two Wreck of the Hesperus films in 1927 and 1948.

Beaches are found all along the Cape Ann coastline. Photo from

Beaches are found all along the Cape Ann coastline. Photo from

Rudyard Kipling’s novel Captains Courageous (later made into a film starring Spencer Tracy) was also partially set in Gloucester, and various other books and films have been set in the area as well, including the 2016 film Manchester by the Sea, which won Kenneth Lonergan Oscars for best director and screenplay.

Gloucester is where the modern-day frozen food industry developed. 

I always thought Birds Eye frozen foods were named for, well, birds’ eyes — after all, birds (with eyes) are prominently pictured on the packaging.

Instead, they were named after one Clarence Birdseye, who lived in Gloucester and developed a flash-freezing technique for fish and later for the frozen peas, spinach, and other vegetables just about every baby boomer no doubt grew up with.

Birdseye owned the General Seafood Corporation, which moved to Gloucester in 1925 and patented his breakthrough processes for freezing seafood, meats, fruits, and vegetables so that they maintained many of the nutritional and taste qualities of fresh foods.

After he sold his inventions to what became the General Foods Corporation, the frozen products were marketed as Birds Eye brand in honor of their originator, who was later named to the National Inventors Hall of Fame.

Bonus Thing:

Gloucester holds an annual mid-summer Greasy Pole Contest, in which (usually well lubricated) competitors try to walk out to the end of a long greased pole situated in the harbor. Needless to say, most end up in the water, 20 feet below, and a fine time is had by all. (Plenty of boats are stationed nearby for rescue purposes if needed). While it’s too late to make the 2018 competition, there’s always next year!

If you go:

For general tourist info, go to the Discover Gloucester site.

The classiest — and priciest — hotel is the oceanside Beauport Hotel Gloucester, which, among other amenities, features a Birdseye Rooftop with Birdseye Pool and Birdseye Bar. (55 Commercial St., Gloucester, 978/282-0008)

For information on B&Bs in Rockport, go here.

For lodgings in Rocky Neck, go here

Go to these sites for Essex river cruises and antiquing

For harbor tours, go here

For whale watching trips, go here

Reader Comments:

Hello! What a great article; I actually own and operate Cape Ann Foodie Tours and our Taste Gloucester tour introduces our guests to all of the great information you’ve collected above. We also discuss the cultural feel of the city and eat lots of delicious local foods. It’s ironic that where you were staying with friends here was a house built for a fishing captain, because my home is also on the harbor (across the bridge, on the Hammond Castle side “off island” as we say here) and was built for a fishing captain. By the same architect that built Howard Blackburn’s tavern – and in the same year, 1900. I am also a writer, however I haven’t published travel articles except for a local online magazine “The Other Cape”. I do have a book on Amazon: “The Luckiest Dog Not Alive”! I look forward to reading your blog. Glad that I found you in Google Search! Cindy Hendrickson


Thanks for writing, Cindy, and welcome to! I’m very glad to hear about your Foodie Tours and to include the info here. As you can tell, I loved Gloucester. You might also enjoy reading this piece by my contributing writer Robert Waite:

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According to government and private surveys:

  • Leading-edge baby boomers (born between 1946 and 1955) and seniors account for four out of every five dollars spent on luxury travel today.
  • Roughly half the consumer spending money in the U.S.--more than $2 trillion--is in the hands of leading-edge baby boomers and seniors.
  • Baby boomers (born 1946-1964) travel more than any other age group.
  • When asked what they would most like to spend their money on, baby boomers answered “travel” more than any other category, including improving their health or finances.

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