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Congress Street in Portland, Maine

A Perfect Day in Portland


By Kathleen Pierce

After unwinding at Cliff House for a few days—dropping your stresses by the sea—you’re calm and relaxed and ready to hit the town. Just a 40-minute drive north, Maine’s largest and foodiest city beckons, filled with James Beard-winning restaurants, retro cocktails, edifying museums, and a craft culture that permeates this port city on the move.

And you’ll be on the move, too. Portland is a walking city, so you can easily work off the homemade pesto dish at Solo Italiano on Commercial Street (led by Portland’s undisputed pesto champ, Chef Paolo Laboa, a native of Genoa).

Pesta Pasta at Solo Italiano in Portland, Maine

Photo credit: Solo Italiano

This harbor town is lined with colorful cobblestone streets and a variety of architectural styles that feel New England to the core. With so many directions to take, how do you pack it all into one day?

Start in the photo-worthy Old Port, where unique independent shops such as Vervacious, a spice emporium, gives way to Cabot Farmers’ Annex cheese tasting bar, a cool kitchen store, and specialty shops you won’t find in most Maine towns.  

Gents, get your shop on at David Wood, a contemporary haberdashery that outfits yachters and hipsters alike. The proprietor spends the offseason in Europe shopping for the sharpest men’s duds. Check out his Italian fabrics, suits, silk handkerchiefs for knockout pocket squares, and if you’re lucky, Wood will pour you an espresso. That’s right: the best espresso this side of Milan happens to be found in his Commercial Street atelier.

Speaking of caffeine, true coffee pilgrims should find their way to Bard Coffee, a few blocks north on Middle Street. The best nitro iced coffee is always on tap and influencers in Portland’s growing startup scene and creative types from Brooklyn, who now call the city home, live here. Pick up on the creative buzz and head out the door for more.

Coffee at Bard Coffee in Portland, Maine

Photo credit: Bard Coffee

The popular peninsula has boats, ships, ferries, and the working port gives it an edge. Want fish? There are scores of places to nab a lobster roll; we recommend The Porthole Restaurant and Pub for the most authentic experience. Located smack-dab on the water, with great stews, views, and chowders, it’s hard to find a place more Maine.

But for a true Seattle-like seafood experience, head to Harbor Fish Market steps away on Custom House Wharf. Locals that line up for the freshest catches around know this fish emporium is an attraction, à la Pike Place, so take a number and get in line. It’s an experience and education to see what local fishermen are catching right now.

Wine Tasting Glass at Cellardoor at the Point in Portland, Maine

Photo credit: Cellardoor at the Point

Portland is a burgeoning city that’s changing day to day, some comparing it to Boston 15 years ago. To sample the cutting edge scene, Uber over to Thompson’s Point. This emerging, former industrial wayside has risen like a phoenix, throbbing with new eating and drinking establishments that are hot to trot. Bissell Brothers, Portland’s punk rock brewer, opened Maine’s largest tasting room here last summer. Hopheads line up at 9 am for their latest releases. It’s always lively and energetic in this graffiti-splashed space with high ceilings and good vibes. Wine lovers should check out Cellardoor at the Point, for a swanky, more feminine version of a wine emporium. Try this award-wining Maine wine and change your mind about grape juice from the Pine Tree State once and for all.

Plan your getaway right and you can also catch the circus. Circus Maine is a school that teaches high wire acts, trapeze stunts, and clowning around. They also have cabarets fairly frequently in this renovated brick loft in the same block as the tasting rooms.

Now that you’re ready to nosh, elegant to casual options abound. If you’re feeling romantic, Timber Steakhouse on Exchange Street is the place to go. Located on one of the most picturesque streets in town (think old London, or Charles Street in Boston), Timber is an exciting option. Perfect lighting, bone-in rib eye, dry aged beer burgers, filet mignon, and an award-wining cucumber gin martini poured by the most regal bartender around, Henry Jost, is the perfect cap to any day.

Scales Restaurant in in Portland, ME

Photo credit: Scales

And because you can never get enough of the water, Scales, the new restaurant backed by the team behind Fore Street—the restaurant that put Portland on the culinary map—is as impressive as they come. The stunning room, with a giant open kitchen, raw bar, succulent seafood, and innovative kelp cocktails, is everything that’s right with Portland now.

Feast on a classic array of Maine seafood before making your way back to Cliff House for a relaxing evening by the sea.

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