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48-Hours in Portland, Maine

Portland truly embodies quintessential New England charm. The seaside town has gained a reputation as a huge foodie destination, once being named “America’s Foodiest Small Town” by Bon Appetit. It also boasts a lively waterfront as well as fantastic art galleries and museums. Summers here are idyllic: the weather is warm during the day, with temperatures rarely climbing above 80º, and cools by the evening. During autumn, there are fewer crowds, the temperatures are mild, and the fall foliage is a sight to see.

Where to Stay

The Press Hotel is located in what was once the Gannett Building, housing the Portland Press Herald, the state’s largest newspaper. In 90 years since the building’s debut, the cobblestoned Old Port District has become one of the country’s most successful revitalized warehouse districts, blending Portland’s working waterfront with a walkable neighborhood of historic buildings housing shops, restaurants and residences. The 110 guest rooms are 1920s-styled with oversized writer’s desks and black reporter’s notebooks to jot down inspirations. The Herald’s city room has been transformed into the popular Inkwell Bar and executive chef Josh Berry is cooking up New England farm-to-table cuisine at the UNION restaurant.

The Portland Harbor Hotel is located in Old Port, walking distance from the city’s award-winning restaurants, art galleries, locally-owned boutiques and shops, theatres and the working waterfront. This is the place to stay if you want to be in the center of it all. The guest rooms are newly renovated with a modern nautical design, with either city or garden views. The hotel’s Blue Fin Restaurant has a seasonal menu that highlights Maine's bounty of fresh seafood and local ingredients.

Seven miles south of Portland is Inn by the Sea, located on a mile of sandy beach in Cape Elizabeth. A multi-million dollar makeover has elevated the Inn into Maine’s premier luxury beach destination, making it an immersive escape from everyday life. Its pristine lawn offers views of the coast, and its poolside patio is the perfect place to spend a lazy afternoon. Inn by the Sea boasts 61 stylish and modern guest rooms, as well as spacious one and two bedroom suites. The Inn also has one of the best spas in the state, and its Sea Glass restaurant focuses on local ingredients and underutilized seafood.

Where to Eat

The centerpiece of the communal dining space at Eventide is a giant Maine granite trough, filled to the brim with crushed ice and fresh shellfish. Photo by Bill Addison for Eater.

This always-packed contemporary oyster bar boasts dozens of bivalve varieties and is popular with tourists and locals alike. While oysters are the focus, the menu also boasts dishes like tuna tartare and lobster stew with coconut and green curry, as well as inventive cocktails . Reservations are limited here—they will only take them for six or more—and there are a number of dates they won't accept reservations at all.

Choose from a selection of small plates at Central Provisions, like this peekytoe crab salad. Photo by Kari Herer.

At this small plates restaurant, chef and co-owner Chris Gould organizes the ever-changing menu into four categories: Raw, Cold, Hot, and Sweet. Mix and match the dishes to create a unique dining experience to enjoy alongside a cocktail from the impressive drinks program. The restaurant was even a finalist for Best New Restaurant courtesy of the James Beard Foundation in its first year.

Duckfat's signature fries are served in a paper cone and make for the perfect savory treat.

If you’re looking for a healthy meal, Duckfat is not the place for you. The restaurant’s signature dish is hand-cut Belgian-style french fries made from Maine potatoes and fried in—you guessed it—duck fat. The house-made paninis and duck poutine are also crowd favorites, especially when paired with a creamy milkshake made with local gelato. There is almost always a line out the door, but if you truly want to indulge, it’s worth the wait.

Must Dos

Local beer and a lobster roll are a must when in Portland, and the Bite Into Maine food truck makes it easy to have both in one place.

Eat a lobster roll at Bite Into Maine food truck — it wouldn’t be a visit to Maine without one! The truck can regularly be found at Allagash Brewery, giving you the perfect excuse to try a local beer while you’re there.

The Portland Head Light lighthouse, museum, and adjacent park make for a great family outing with classic coastal views. Photo by Cynthia Farr-Weinfeld.

Visit the Portland Head Light, Maine’s oldest and most photographed lighthouse. The onsite museum is a great place to learn about the lighthouse’s history.

A mailboat tour combines a scenic cruise with a real working boat, allowing for a unique way to see Casco Bay.

Experience Casco Bay on the Mailboat Run! The charming three-hour boat ride gives riders a chance to see Great Diamond, Little Diamond, the Cliff islands, and plenty more.

The Portland Museum of Art is the oldest and largest public art institution in Maine.

Stroll through the Portland Museum of Art, which houses works by Edward Hopper, Picasso, Matisse, Monet, and many more.

Portland is just one stop to consider in Maine. Kennebunk is a charming town with some wonderful properties including one of our favorites: The White Barn Inn. We can offer special amenities such as upgrades, hotel credits and a behind-the-scenes tour of the kitchen at the celebrated restaurant.


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