When you stumble out of a bar that has been around for over a hundred years, having just guzzled four glasses of thick Boston lager, walk head-first into the open wharves, hear the echo of gulls overhead, and have to fend off an equally drunk man trying to steal your phone, you know that you’re in Gloucester. And it is the best feeling in the world.

Each year, millions of tourists pour onto the beaches and harbors of this tiny seaside community. Summer attracts the more opportunistic, more ambitious, and more barbarous. They come far and wide to tour Gloucester Harbor and all her famous sights: Ten Pound Island, Thatcher Island, Dog Bar, Norman’s Woe Rock, Half Moon Beach, and Eastern Point. Some even slither through the remnants of the Andrea Gail. The city’s piers and taverns are quickly overrun by visitors, shouting and chomping their way through the placidity, hoping to taste the soft meat of the morning’s catch. But when you get caught in this hot, white delirium, you tend to reappraise your entire trip because this is not how Gloucester is meant to be experienced.

A quiet street corner in Gloucester, Massachusetts

Gloucester, purportedly America’s oldest seaport, has a long, rich history of maritime tradition. In the old days, it was an essential shipbuilding port that provided close passage to the fishing grounds in Nova Scotia and Newfoundland. Back then, you could walk up the steps of city hall and look over the hill to see smoke columns billowing out of the white Georgian homes. If you take a deep breath today, you’ll recognize the smell of drying redfish hanging in the air. If you listen carefully, you’ll hear the fluster at the auction wharf, white caps erupting against the breakwater, fog horns rolling out of the harbor, and boats hurtling out to sea. To put it plainly, Gloucester is not meant to be a resort town — it’s too tough. It’s a place of work and commerce, but these features are why its shores are so infectious and attractive.

What exactly is the real Gloucester, you may ask? Where can you find it? The answer is simple: at the crest of October, just as November quietly invites itself in. After the rain washes the docks and the fog rolls off the shore, the cold, thin air encourages visitors to look for warm places to drink. The skies are still gray this time of year, and you can feel the icy gales pinching at your cheeks. Most dockside patios remain closed, and the storms repel the last remaining tourists from the beaches. But the locals embrace the winter because bad weather opens the roads, allowing the city to breathe again.

A statue of a sailor in Gloucester, Massachusetts

As you walk down the rain-slicked coastline, you might catch a gull chasing a clam as it rolls back into the water. A little farther down, past the downtown hustle, lies the Fisherman’s Memorial, a solemn monument honoring those lost at sea — 249 alone in 1879. Gazing into the stubborn eyes of that bronze statue, all of the historical weight suddenly bears heavy. This is the true face of Gloucester. It is fixed on the violent horizon, every muscle pushed to its limit to keep the wheel steady against the undulating mouth of the Atlantic.

In spite of Gloucester’s location and doleful past, its people remain friendly and wholesome. Drivers will stop in the middle of the road to let visitors cross, and each restaurant comes with a fresh crop of locals eager to recall stories of the big catch. With a bit of luck, one of them might invite you over for breakfast, and just as noon peeks around the corner, they will show you the best vantage point in town. Looking over the city’s chimneys and steeples, a portrait of rustic American heritage emerges. It is cold and cloudy, but honest.

A historic building in Gloucester, Massachusetts

At the Crow’s Nest, beer cascades freely and photographs of the fated Andrea Gail crew, who drowned during the Perfect Storm, adorn the walls in homage. Young fishermen and their girlfriends play pool, but the bar remains an outpost for the salts. It is a refuge for Gloucester’s backbone. Here, everyone is either jaded or silly with inebriation, stories and politics are traded like baseball cards, and the vocabulary seems to be swears and nautical jargon — Greek to everyone else. The expression that hangs over the bar reads: “In cod we trust.” It is a place where the party is always in full swing, but down the street is a different shanty.

At Captain Carlos, trivia night is king. Moms and dads who relinquished their children to some poor high school student get fully toasted by cold ale. Though the best lobster in town is up the road at Gloucester House, the nachos at Captain Carlos will always prevail. Joining the trivia competition can be challenging, but the evening crowds are encouraging to new faces. Despite the fact that answers are written on cocktail napkins, there is no stopping the fiery, steel momentum of Gloucester’s residents.

Old, colorful homes in Gloucester, Massachusetts

At Halibut Point, nights end with a few hot ciders; bad weather news from the Northeast Channel, up the Scotian Shelf, and around the Grand Banks to Flemish Cap; cold oysters; and warm cod, served up like pancakes. When the clock tips to midnight and everyone begins the long shuffle home, one final toast rings out into the night. A toast to the vendors who fight to keep their doors open in the digital age. One more drink, one more win for the little guy.

But regardless of where you go, you’ll find that people in Gloucester know and trust each other.

The open waterfront in Gloucester, Massachusetts

America was built on the shores of places like Gloucester. The weathered rocks and rolling hills bristled by pines were the first images settlers saw before stepping onto the New World. Hundreds of years later, those first communities — those trees and rocks are still there. When you finally breach the top of Stage Fort, and you catch a glimpse of that quiet cove waking up to another cloudy weekday morning, you’ll understand this notion. We sometimes forget that our country began on the edge of the sea just like our prehistoric ancestors.

The spirit of this city will excite the deepest, rawest nerve in your body. It will feel like electricity, a powerful current that inflames and invigorates the senses. As you drive away, you’ll find yourself still shaking from elation, and when you are finally home, reeling back from your great adventure, a smile will move across your face. It is then that it becomes clear: a part of your heart was left in Gloucester. Maybe one day soon you will return to find it.

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Rick Romanowski
Rick Romanowski is a writer, video editor, and storyteller based out of Chicago, Illinois. Ever since a particularly doomed high school road trip to St. Louis, travel has always been a part of his DNA. He now scours the globe trying to capture the spirits of adventure and humanity, firmly believing in total cultural submersion. His hobbies include coffee, classical history, cinema, and astronomy.