Just a couple of hours north of Boston, this small coastal city offers lots to do and see.
Many city trips require itineraries that navigate train systems and a patchwork of neighborhoods, but Portland stands out for its walkability. In just 10 minutes, you can stroll from one end of the Old Port to the other. This compactness breeds spontaneity. You can walk past the brick Victorian buildings down small side streets and get lost in shops, indie bookstores, and world-class bars and restaurants.
No matter the weather, the city is open for business, and there’s something magical about a foggy day when salt air drifts through alleyways and you can post up in a coffee shop or bar. A trip to the seaside city demands a climb up through the Munjoy Hill neighborhood to the Eastern Promenade, where you will be rewarded with a view of the hundreds of islands that dot Casco Bay.
Portland is located in the southern region of a state with more than 80 percent wilderness. It comes as no surprise that living up north tests one’s ingenuity, and that entrepreneurial spirit flourishes throughout the Portland scene. Portland welcomes the homespun, the handmade, and the offbeat. The tiny city also utilizes local farms and working waterfronts to deliver fresh, locally made ingredients.
Where to Stay
The Old Port is where you find the cobblestone streets and most of the city’s restaurants and shops. Many city hotels are tucked here, too, including classics like the Portland Harbor Hotel, the Portland Regency, and the stylish Press Hotel in a former newspaper building.
If you crave a quieter landing spot, the West End has boutique stays like Blind Tiger or the West End Inn. Up on Munjoy Hill, options are fewer, but some cozy Airbnbs have rooftop views. An option for the adventurous is a stay on one of the islands. The Inn on Peaks Island is a 15-minute ferry ride with sunset views. Diamond Island’s Inn at Diamond Cove feels like a well-kept secret with thoughtfully designed cottages, a pool, a cabana bar, and a restaurant all on a car-free island in Casco Bay. Of course, island stays require more planning around the ferry schedules. And yes, water taxis are an option but probably don’t miss the ferry.
Where to Eat
Where do we even start? Perhaps with coffee and donuts. Bard Coffee doesn’t disappoint; Holy Donuts, made with Maine potatoes, are dense and delicious. Becky’s Diner has been serving traditional breakfast since 1991 (they also have lunch and dinner menus).
When ready for the state’s famous crustacean, opt for the brown-butter lobster roll at Eventide. If there’s a wait (which is likely), pop across the street to Tomaso’s for a beer and a shot. Nearby, Fore Street, Street and Co, and Scales were all founded by Portland chef legend Sam Hayward. Over in the West End, Pai Men Miyake has ramen bowls you will surely dream about. Across Congress Street is Local 188, where you can grab tapas and cocktails, and Boda for Thai food (which stays open late on weekends). Portland Lobster Company has the classic lobster roll and is a casual place on the water that has live music every night of the week. Maps is a bar for cartophiles that plays records and serves grilled cheese and cake. New spots are always popping up, so keep an eye out and let yourself wander into places that beckon you inside.
What to Do
Portland is very walkable. Visitors might want to bring their gift lists and stop into local gems like Sherman’s Books for new and nostalgic titles, Pinecone and Chickadee for unique gifts that make you smile, Folly 101 for stylish home goods, and Blanche + Mimi for housewares, toys, and gifts.
When the weather cooperates, head out on Casco Bay. Portland Paddle organizes kayak and standup paddleboard rentals and tours. Maine Island Trail Association has a map of accessible islands. But maybe the chilly harbor waters aren’t tempting you; that’s okay. You can still enjoy the bay by riding the ferry. The Portland Encylepedia rents bikes and gives tours of Peaks Island and local lighthouses.
Portland Head Light is not in Portland; it’s in Cape Elizabeth, but it’s worth the 15-minute drive. Fort Williams Park surrounds the beacon and is a beautiful walk, and a gift shop in a former lightkeeper’s house has rotating exhibits. Is live music more your thing? Check out the Thompson’s Point, Maine State Pier, One Longfellow Square, State Theater, and Portland House of Music lineups.
If you have kids with you, there are plenty of fun activities: You can ride the mini train near the waterfront, explore the Eastern Promenade, or spend an afternoon at the Children’s Museum. However you choose to spend your Portland weekend, you will find there’s something for every age, pace, and curious wanderer.
