With a combination of New England seaside charm and metropolitan energy, the stylish seaport of Portland is home to historic buildings, award-winning restaurants, and a working waterfront. The abundance of unique, locally owned boutiques, eateries, and markets provides something for everyone in Maine’s largest city.



A new venture from the creative couple behind Portland Hunt and Alpine Club, the West End’s Little Giant is bright and welcoming on this 10-degree evening. Bar manager Max Overstrom-Coleman greets my boyfriend, Sean McCarthy, and me and walks us through the restaurant’s innovative cocktail menu. Sean picks the Knife Fight, a bourbon-based drink, and I get the hot buttered rum. Both begin to warm us from the inside out. We order a snack of fried oyster tacos and plan what old haunts we will visit and what new gems we hope to uncover in our home city.

We head just up the street to check in at our weekend accommodations, the Danforth Inn. The 1823 brick mansion is a modern oasis of tranquility with impeccable decor and design. We quickly settle into the Old Port room and prepare for dinner. Dining at Tempo Dulu is a one-of-a-kind experience. At the recommendation of the knowledgeable staff we order the rijsttafel, an Indo-Dutch feast with multiple small plates. Our fireside table for two is soon crowded with heaping bowls of fluffy rice, tender beef rendang, chicken satay, and more. We opt for the wine pairing and are treated to one of the best selections of wines we’ve had in Maine.



We rise before the sun to a subzero day. Bundled up tight, we visit the Danforth’s charming cupola to watch the sun rise over Portland. The inn offers a luxurious breakfast spread, but we have another West End spot in mind: Ilma Lopez and Damian Sansonetti’s newest endeavor, Chaval. We belly up to the bar next to the warmth of the kitchen, and we have a great view of Sansonetti and his team during brunch service. Veteran Portland bartender Patrick McDonald mixes us up a few delightful breakfast beverages, including a Garibaldi with Campari and orange juice—freshly squeezed to order—and a Bloody Mary with sherry. Our three entrees—the Spanish Breakfast, the Iberian bomba rice bowl, and the beef cheek hash—are warm and comforting and show the attention to detail that the husband- and-wife duo is known for. We know we have a big day of eating ahead of us, but we can’t resist trying Lopez’s churros. Chaval is everything you could hope for in a brunch.


We start our journey on Commercial Street. Housed in the E. Swasey and Co. Pottery building, Suger is home to designer Roxi Suger’s Angelrox brand, a beautiful, sustainable clothing line made by hand in a historic mill in Biddeford. Across the street, Browne Trading Company is known for its pristine seafood and fine caviar. We browse the store’s tremendous wine selection and select a dry Riesling as a souvenir. We embrace the cold for a short exploration of the piers and docks that make up Portland’s working waterfront before ducking in to Harbor Fish Market to take long, deep breaths of the salty smell and inspect the fresh oysters on ice.

We move a little farther inland to explore the Old Port. Relatively new to the scene, Ramblers Way on Market Street has organic merino wool clothing that seems especially cozy, considering my chilled bones. Portland Art Gallery, just across Middle Street, showcases a variety of talented Maine artists and is the perfect stop for a moment of quiet contemplation before we continue our journey along the cobblestones to the Salt Cellar. Co-owner Judit Vano-Tydeman greets us with a warm smile and leads us to the salt vault, where she explains the many benefits of halotherapy.

We round the corner to explore the shops and restaurants that line Exchange Street. Folia Jewelry is our first stop. We wander around the small glass boxes and admire owner and artist Edith Armstrong’s beautiful designs. Just a couple doors down is Abacus Gallery. Surrounded by a perfectly curated selection of art, jewelry, and decor, we catch up with owners Sal Scaglione and Dana Heacock, who tell us some of the history behind their five Maine stores. I ogle their selection of Ed Levin jewelry until it’s time for another snack.

A visit to Portland isn’t complete without a stop into the Holy Donut. The Maine potato-based doughnuts come in a variety of eclectic flavors, such as maple bacon, pomegranate, chai glazed, and my personal favorite, dark chocolate with sea salt flakes. Fully recharged, we walk to Skordo. Family owned and operated, Skordo is the perfect resource for any level of home cook. We peruse the store’s plentiful spice racks, sample a few spices, and leave with a cookbook, an Ethiopian spice mix called berbere, and every intention of becoming regulars.


Liquid Riot Bottling Company, besides being a restaurant and bar, is also a distillery and brewery that churns out an impressive list of libations, including an award-winning fernet. We snack on poutine and sip fernet as the light fades on Portland’s working waterfront.

With a decor that pays homage to the city’s maritime history, Blyth and Burrows has dim, atmospheric lighting. We settle into a booth on the middle level of this three-tiered bar, right next to the inconspicuous entrance to the secret bar downstairs. I stay on the fernet train and order the H.M.S Boxer, and Sean orders the Penny Cap, which comes with a side of bottled smoke. At the recommendation of many, we order the Poke Bao, which is the perfect bite to hold us over until dinner.

Although it is surrounded on all sides by busy city streets, Union’s elegant dining room is calm and sophisticated. Sean and I take a table for two by the plate-glass windows. Executive chef Josh Berry has created a menu that boasts ingredients from many Maine purveyors. I order the truffle beef pot roast off the signature chef’s dishes menu, and Sean opts for the braised local rabbit with white corn polenta. Union’s menu is a beautiful reflection of the farmers and fishermen of Maine, as well as Berry’s talent.

We arrive back at the Danforth Inn chilled to the bone and know the perfect antidote awaits us at Opium. The inn’s dark and moody cocktail bar is filled with purple light while a DJ provides the soundtrack for the evening and bar manager Alexa Doyer mixes up some exquisite cocktails. We can’t resist the Jakarta, which arrives with an empty glass placed over smoking Chinese spices with bitters, vermouth, rye, and absinthe to top it off.



Tandem Coffee and Bakery, a modern bakeshop in a former gas station, is the perfect place to start the morning. On entering we are greeted with a bakery counter lined with biscuits, pastries, and pies of all shapes and sizes. We sip two lattes, share one of baker Briana Holt’s famous loaded biscuits, and watch as the shop fills up with the morning crowd.

We head off-peninsula for brunch. One of the pioneers of the Woodfords Corner neighborhood revitalization, Woodford Food and Beverage is housed in a midcentury modern building at a bustling Portland intersection. The interior is bright and inviting. I enjoy a classic and satisfying brunch of eggs and coffee, and Sean gets a little more adventurous with Woodford’s take on eggs in purgatory. We soak up the sun streaming in from the large windows that face the evolving neighborhood.

As we make the short trip back to our apartment in Portland’s Parkside neighborhood, we reminisce about our staycation weekend and are overwhelmed with gratitude that we can call this charming city home.