A Maine winter evening in Portland
The winter day in Portland had the kind of gray light that lingers, the sky stretched low over the city as if it wanted to press us closer to the ground. Snow had been falling lightly since morning, clinging to rooftops, softening the cobblestone streets of the Old Port, turning every corner into a postcard. We parked the car near the wharf, bundled against the wind, and stepped out into the hush of the evening. The snow crunched beneath our boots, sharp and clear, each step ringing like its own quiet song. The air carried the briny scent of the Atlantic, colder than you can describe, wicked cold, the kind of cold that defines Maine and shapes its people.
Walking through the Old Port in the middle of winter feels like stepping into another time. The brick buildings, their windows glowing warmly, stood proud against the gusts off the harbor. Shops and cafés dotted the streets, but unlike the summer months when tourists crowd the sidewalks, winter belongs to the locals. There is something peaceful about these long winter days when the streets are quiet, the wharf covered in glistening snow, and the only sounds are the wind and the distant gulls that never seem to leave Portland, no matter the season. It is Maine at its most honest.
We pulled our scarves tighter, laughing at the bite of the wind, heading down toward the water. The snow swirled around us, flakes settling on coats and eyelashes. The lights along Commercial Street flickered against the snowy air, leading us like a trail toward our destination: DiMillo’s on the Water. It isn’t just a restaurant, it’s a floating landmark, a ferry turned into a dining room where memories are made. For us, it was the place where we had celebrated countless New Year’s Eves, where the sound of clinking glasses and laughter had welcomed another year. To walk toward it in the heart of winter felt like coming home.
Inside, the warmth wrapped around us like a blanket, the sudden contrast almost dizzying after the sharpness of the cold. Coats unbuttoned, gloves tucked away, we stepped into the glow of DiMillo’s. Guests were already gathered at the tables, cheeks pink from the weather, leaning over bowls of steaming chowder. The air was thick with the scent of lobster, butter, and fresh bread. The servers moved quickly, balancing plates of Maine lobster, steam rising from the shells, the crack of claws punctuated by bursts of conversation. There was happiness here, the kind that only comes from escaping the cold into a place where the food is hot, the company familiar, and the view outside reminds you just how good you have it.
We settled in, ordering our usual: chowder to start, then lobster, bright and red. Eating lobster in Maine is never just about the food; it’s an experience, a tradition. The cold outside makes the warmth inside sharper, the flavors richer, the moment fuller. Each bite carried with it the salt of the ocean, the story of the harbor, the memory of all the times we’d been here before. We laughed as the butter dripped onto the table, remembering past New Year’s toasts, summers when the place overflowed with visitors, and the quieter winter nights like this one when the restaurant felt like it belonged just to us.
Through the windows, the snow kept falling. The harbor was still, the boats rocking gently, the water black beneath the gray sky. Lights along the dock twinkled, reflecting in the water, blurring with the snowflakes. It was a Maine winter evening in all its quiet glory: peaceful, unhurried, wrapped in the kind of beauty that doesn’t need to announce itself. This is Portland in the winter, this is Maine, and yes, this is the way life should be.
As we finished our meal, sipping the last of the wine, the room around us hummed with warmth. Laughter rose from nearby tables, a child cracked open a lobster claw with triumph, and the servers moved swiftly, as if dancing to the rhythm of the night. Outside, the storm carried on, steady and sure, blanketing the city in silence. We stepped back into it at last, bellies full, hearts warmer, pulling our coats tight once again.
The snow crunched underfoot as we walked back toward the car, the Old Port lit with the soft glow of streetlamps and the shimmer of fresh snow. The harbor was hushed, the boats rocking in rhythm, gulls tucked into their wings. There was no rush, no noise, only the steady sound of our footsteps and the whistle of the winter wind. It was the kind of evening that makes you pause, that makes you grateful, that reminds you that Maine is not just a place, it is a way of life. Wicked cold, yes, but also wicked beautiful.
Explore art from this Collection
This story is part of our Wicked cold Collection, a series of large postage stamp wall art celebrating Maine. Each artwork captures the colors, textures, and spirit of Maine through a lens of travel and memory. Discover related pieces like Wicked cold No.1 and Wicked cold No.2, or explore all works in the Wicked cold Collection.
Each piece is designed and printed in large-format detail; a postage stamp for your walls. View all collections or learn more about Ana.
