A Local’s Guide to Portland, Maine and Beyond

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Visitors often come to Portland, Maine, for the first time because they want to spend a summer weekend in a quaint city by the water, or because they’ve heard about the city’s superlative seafood (80 percent of the United States’ lobster comes from Maine). Seduced by the easy access to nature and relative affordability, many return for longer stays or even for good. Between 2020 and 2022, Maine’s population had the highest percentage increase of any New England state.

But Maine’s desirability is nothing new. Artists, artisans and writers have long gravitated to the state; they established an art colony with two schools of painting in Ogunquit, on Maine’s southern coast, in the first half of the 20th century, and the Haystack Mountain School of Crafts on Deer Isle, which was founded in 1950, continues to draw instructors and students from around the world. More recently, the state’s creative spirit has resulted in a dynamic food scene. Turn down any one of one of Portland’s cobblestone streets and you’ll find more quality restaurants and bakeries (of both the old- and new-guard varieties) than you might expect in a place with just 68,000 year-round residents. The same is true just northeast of the city, in the mid-coast region, especially in the town of Rockland — an easy and scenic 90-minute drive away — which has a burgeoning food and art scene on track to rival Portland’s.

Kazeem Lawal, the owner of the clothing and accessories store Portland Trading Co., moved from New Jersey to Portland 14 years ago, and has witnessed its stratospheric growth from a small port town to a destination city. “It’s a bit like the Brooklyn of 20 years ago, with old and new coexisting,” he says. “and it’s continuing to grow and evolve, as all cities should and do.”

Here, Lawal and three other Mainers share their favorite spots in and around the state’s largest city.

The Insiders

Alex Day, a co-owner of Death & Co. cocktail bars (with locations in New York City, Los Angeles, Denver and Washington, D.C.), moved to Portland in 2019.

Lily King, the novelist, has lived in Portland since 2002.

Kazeem Lawal, the creative director of the…