For many years, a food industry friend of chefs Damian Sansonetti and Ilma Lopez had been inviting them to visit Portland, Maine. But the couple – who were living and working in New York City — had no interest in this small city along the southern Maine coast. Finally, Damian and Ilma decided to escape there one weekend and it was love at first sight. “We fell in love with the town and the landscape and the raw materials: the ocean and the fish and the farms,” says Damian. After visiting four times over the course of nine months, they decided to ditch NYC and head north. Now, their much-lauded Chaval — a Spanish-French brasserie — is such an integral part of the local food scene that the James Beard Foundation called Damian and Ilma one of Maine’s “power couples.”

This city has that kind of an effect on people. “I always say Portland picked me, not the other way around,” says Kazeem Lawal, who opened a modern-era general store called Portland Trading Co. and launched The Maine African Film Festival. “I fell in love with the city because of its innocence and the feeling the city was ripe for fresh new ideas — room to bring something new to the table.”

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Rachel Adams, who paints murals alongside her husband, Ryan Adams, has a similar story: The multidisciplinary artist moved here to attend college and never left. “Portland was a hub for creatives in visual art, music, and food — affordable and unsuspecting,” says Rachel. “Like everything, Portland has changed, but there are still pockets of that magic, if you know where to find them.”

So for this issue of The WeekEnder, we’re going to tap into locals like Damian, Ilma, Kazeem, and Rachel and tell you where to find all the magic — from the best seafood spots to boutiques that will stop you in your tracks to outdoor adventures that will have you considering making a move to Maine yourself.

-Laura Begley Bloom, New York's Senior WeekEnder Writer

Editor’s Note: For the latest on Covid in Maine, visit the state’s official COVID-19 information page.

The Press Hotel

Located in an historic Old Port building, the Press Hotel pays homage to its past life as the headquarters of the Portland Press Herald newspaper with thoughtful design details like a two-story wall lined with vintage typewriters, wallpaper imprinted with headlines from old articles, and a carpet that has letters strewn about. The iconic property also celebrates Maine artists at the in-house gallery and keeps foodies satiated at two excellent in-house restaurants: Union and Inkwell. Another thing going for the Press: It’s right in the middle of everything, so you don’t need a car to get around.

Honorable Hotel Mentions

For Instagrammers: Blind Tiger - A Federal-style mansion from 1823 has been transformed into a chic urban inn, complete with a basement billiard room set in a former speakeasy. Don’t miss the skyline and harbor views from the rooftop cupola.

For art lovers: Canopy Portland Waterfront - Right on the water in the Old Port neighborhood, the Canopy features unique pieces of art from more than 20 Portland-area creators. The hotel lends guests free bikes to buzz around town.

For living like a local: Best Bower - In a converted church right next to the Portland Observatory, this six-room guesthouse operates like an Airbnb — but better. The restaurateur owners can hook guests up with locally sourced provisions like beer, wine, and snacks to sample a taste of Portland.

For sweethearts: Chebeague Island Inn - Set on an island just a stone’s throw from Portland and only accessible by boat, this 1880s inn is made for people who want to slow down and experience Maine like it used to be.

The food scene in Portland is staggering. “You can eat and drink yourself silly for however long you’re here and not repeat anything,” says Damian Sansonetti. “And I know I’m biased, but the all-around quality of the restaurants is so high that I have a harder time telling people where to go here than when we lived in New York City.” To Damian’s point: There’s not enough space to include all the restaurants that our insiders love, but here’s a highly curated hit list.

Best breakfasts

Hot Suppa - One of Rachel Adams’s go-to spots for breakfast. Don’t miss the biscuits and gravy and the Cajun Bloody Mary garnished with pickled okra.

Local188 - Another Rachel favorite. The breakfast burrito is legendary.

Rose Foods - Famous for golden bagels that are soft inside and crusty on the outside; top them with pastrami-style lox.

Coffee break

Speckled Ax - “We’ve known Matt, the owner, for quite a long time. All his coffee is organic and wood-roasted and he does funky things like beans aged in Allagash beer barrels,” says Damian.

Tandem Coffee - A sleek cafe in a converted gas station with house-roasted coffee and sweet-and-salty biscuits that Bon Appetit raved about for being flaky beyond belief.

Lunchtime

Mr. Tuna - This beloved food truck on the Eastern Promenade serves up the freshest sushi. “It’s my favorite lunch spot,” says Ilma Lopez. Order a hand roll and soak in the killer views of Casco Bay.

Salt Yard Cafe - The industrial-chic cafe with a wood-fired oven was named after its next-door neighbor, which produced salt-glazed earthenware in the 1800s.

Bissell Brothers Kitchen - One of the state’s hottest craft breweries opened this adjacent lunch spot that specializes in modern Maine flavors like a beer-battered pollock sandwich with honey miso butter glaze.

Casual eats

Flatbread Company - “A great place to take your family — they make pizza and salad but also have an incredible beer list on tap for adults,” says Matt Ginn, executive chef for EVO Kitchen + Bar (see below) and the Chebeague Island Inn.

Woodford F&B - “When we go out with our daughter, we go here,” says Ilma. “She always gets the steak frites, I get the crabcakes, and Damian gets the burger and the deviled eggs.”

Terlingua - Texas barbecue, a massive mezcal menu, and even some plant-based treats for our vegetarian friends.

Seafood

Luke’s Lobster - Maine native and third-generation lobsterman Luke Holden started a small empire by sharing the quality, affordable lobster rolls of his youth. Here, you can sample what made him famous in a captivating waterfront space on Portland Pier.

Highroller Lobster Co. - A cultlike food cart was transformed into a bricks-and-mortar location where people still line up for the lobster rolls.

Eventide Oyster Company - This isn’t just any old oyster bar: Eventide is a James Beard Award winner.

Global bites

Asmara - “One of my favorite restaurants is this tiny Ethiopian restaurant off a side street. It’s been here forever and the owner cooks in the back,” says Damian. “It’s like you’re eating in Ethiopia.”

Izakaya Minato - “A couple-owned restaurant with small Japanese plates,” says Damian. “The chef is a fun dude and if you sit at the counter, he will chat you up all night.”

Baharat - Instead of a fussy tasting menu, this restaurant serves a bakery tray filled with a shareable mix of Middle Eastern and Mediterranean staples.

EVO Kitchen + Bar - A fusion of Jordanian, Turkish, and Syrian flavors, thanks to one of our insiders, chef Matt.

Banh Appetit - This simple storefront serves up Vietnamese-style sandwiches and noodles.

Date night

Chaval - Romantic yet relaxed, Chaval is a welcoming neighborhood brasserie from Damian and Ilma, who change the menu seasonally, except for two staples: the coq au vin and the burger. They also cure their own jamón and make patatas bravas and pan tomate that’s the next best thing to a trip to Spain.

Leeward - Handmade pasta and Maine-sourced ingredients helped propel this Italian spot in the Arts District onto the shortlist for Best New Restaurant at 2022’s James Beard Awards.

Via Vecchia - In an ivy-covered Old Port building, you'll find a sultry slice of Italy with crystal chandeliers, velvet banquettes, and a modernist menu.

Twelve - Set to open any day now, this highly anticipated farm-to-table restaurant will be led by chef Matt and Colin Wyatt, former executive sous chef at NYC’s Eleven Madison Park.

Drinks

Crispy Gai - “If you like fried chicken and South Pacific-inspired cocktails, this is your place,” says Ilma.

Luna Rooftop Bar - The place for pre- or post-dinner drinks with stunning panoramic views.

Batson River Brewing - Craft beers and spirits that are like Maine in a bottle.

Cocktail Mary - “When you get cocktails at Cocktail Mary, see Isaac,” says Damian. “That’s what I love about Portland — the people.”

Sweets

Dear Dairy Ice Cream - “Be sure to leave room for Dear Dairy ice cream,” says Rachel. The reward: homemade scoops like brown butter caramel and 24k gold, a sweet and spicy mix of roasted carrots, fresh ginger, and turmeric juice cooked with coconut.

On the water

“I always recommend going on a ride to see the surrounding islands and to enjoy the freshness of the ocean,” says Kazeem Lawal. Check out these three cool ways to experience Portland by sea.

Lucky Catch Cruises - On a cruise through Casco Bay, you can learn about the art of lobster fishing and catch your own dinner.

Rocky Bottom Fisheries - This authentic Maine fishing boat has a lobster tour where you can haul and set traps, plus a sunset tour for cruising along the coast.

Sail Portland Maine - Explore the coastline on a sailboat or a classic Down East picnic boat.

Arts and culture

It’s no surprise that works from our artist insider, Rachel Adams, can be found at some of the top cultural spaces in town. Here are three not to miss.

Portland Museum of Art - An inclusive space that champions Maine’s rich artistic legacy while also exhibiting works by legends like Claude Monet. The shop sells a small collection of Rachel’s printed clothing. Fun fact (and a fun detour): The museum also owns and operates the Winslow Homer Studio in nearby Prouts Neck.

One Longfellow Square - This music venue in Portland’s Arts District venue also showcases film, theater, and dance performances.

Children’s Museum - Kids lead the way in 30,000 square feet of interactive spaces. And yes, those are Rachel’s murals you see.

Shopping

Craftsmanship and individuality help elevate Portland’s retail scene into more than just shops — these are true design destinations.

Portland Trading Co. - A modern general store with everything from shaving blades to killer cocktail dresses. “Part of the uniqueness of the store: I travel to different parts of the world to source and get inspired, so that keeps it vibrant and interesting year in year out,” says owner Kazeem Lawal.

Loquat Shop - This cutting-edge shop sells the work of entrepreneurs and marginalized artists, plus Rachel Adams’s printed clothing.

Plant Office - Living plants and floral design.

Kurier - Handcrafted clogs, sustainable leather handbags, and other locally made finds.

Ferdinand - Green, ethical, and vintage designs ranging from earrings to cards to journals.

Herself - Everyday elevated basics for women that are designed and developed in Portland and made from natural fiber fabrics.

GoGo Refill - An eco-chic shop with low-waste goods for the home and body. BYO container or buy one of their gorgeously designed pieces onsite.

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