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This story was published before Summer 2021, when we launched our new digital experience.

How to Do Maine: Three Ways

Planning a last-minute escape? Experience the much-loved destination before summer’s end with a trip to one of these three very different locales.

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If you think Maine is a destination reserved for hermit homesteaders and intrepid fishermen, you haven’t spent enough time “Down East.” Due to its craggy coastline, the easternmost state technically has more miles of tidal shore than California, with inlets and waterways creating prime seafood conditions, unique paddling trails, and some of the most arresting views in nature. Take a last-minute summer weekend to experience the very best of Vacationland: from caught-that-day lobster to untouched beaches to a new boutique hotel. Here, the three places you should visit depending on your state of mind.


Perhaps most famous for being the home of the “Bush compound,” Kennebunkport has long been the family getaway for the political dynasty, and for good reason. Full of local shops and restaurants, and situated next to some of Maine’s nicest sandy beaches, Kennebunkport is perfect for the weekend traveler looking for a mix of town and country.

Originally a sea captain’s house, the 16-room Captain Jefferds Inn (Rooms from $250; 5 Pearl St.; 207-967-2311; has been run by proprietors Sarah and Erik Lindblom for 12 seasons. Like many old-school B&B’s, each room is unique, many contain fireplaces, and they all offer the same amenities one would expect from a luxury hotel (600 thread count sheets)—and then some: their Pearl Essence towels are made from a fiber harvested and spun from crushed natural pearls, and a crystal bottle of brandy left out downstairs for a nightcap. Breakfast is a three-course affair with dishes like apricot French toast, fresh fruit salad, and homemade almond scones. For those who don’t feel like making new friends at the large communal dining table so early in the morning, there are also tables available for two or four.

For the hands-down best lobster roll on the eastern seaboard, head to the Clam Shack (2 Western Ave.; 207-967-3321;, located on a bridge overlooking the Kennebunkport River. Proprietor Steve Kingston bought the no-frills seafood joint and adjoining market in 2000 and has turned it into an award-winning eatery. Kingston is committed to his lobstermen and treats their catch with a purist’s reverence: Lobsters are boiled in seawater pumped from the river below, shucked immediately, and then the tail and claw meat is piled into a freshly baked yeasty roll, smeared with your choice of butter, mayo, or both.

Climb aboard Rugosa Lobster Tours’ (95 Ocean Ave.; 207-468-4095; classic New England wooden lobster boat—which in the summer departs daily from the Nonantum Resort, half a mile down from Dock Square—and either take part in hauling lobster traps from the ocean floor, or sit back and enjoy the coastline. Advance purchase is required, so book online for the hour-long tour beginning at 10:30am, 1pm, or 3:30pm.


Ten miles off the coast of Portland, Chebeague is only reachable by a private boat or chartered ferry, which departs from two locations: Casco Bay Lines from Portland and Chebeague Transportation Company from Cousin’s Island in Yarmouth. The ferry from Yarmouth lands right at the base of the Chebeague Island Inn (Rooms from $225; 61 South Rd.; 207-846-5155;, a beautifully restored hotel from the 1920s set on a hill overlooking the bay. The rooms are modest but comfortable, with west-facing views of the ocean and spectacular summer sunsets.

The beauty of traveling to an island is that a to-do list becomes satisfyingly simple. Grab a bicycle from the rack out front and head to one of six pristine beaches just a short ride from the inn, play tennis on the clay courts at the Chebeague Tennis Club, or a round of nine holes at the Great Chebeauge Golf Course, which is listed on the National Register of Historic Places. In the evening, enjoy a cocktail on the inn’s wraparound porch or play cornhole on the lawn and work up an appetite for the onsite restaurant’s menu of local and seasonal fare. The mussels are sourced from an island across Casco Bay, the broth tangy and full of chorizo, and the zucchini used in the gazpacho is picked directly from the kitchen garden out front.


It’s no secret that “the other Portland” has foodies, hipsters, and nature-lovers flocking to southern Maine. With a host of talented restaurateurs, locally brewed beer, and independent cafés, native Mainers often joke that there’s a non-stop subway line running straight from Brooklyn to Portland—admittedly, many Brooklynites have moved to the place. The newest addition to the burgeoning city’s downtown scene is The Press Hotel (Rooms from $290; 119 Exchange St.; 207-808-8800;, the city’s first and only luxury boutique hotel. Located in the old Portland Press Herald newspaper building, the fact that The Press is the first of its kind doesn’t mean it feels plunked down. Rather, Autograph Collection took obvious care in embracing the history of the building. Much of the original architecture remains intact, and local artist Erin Hutton’s “Typewriter Wall,” a two-and-a-half story art installation of vintage typewriters, is one of the first things you’ll see upon arrival. Copies of the Portland Press Herald are delivered to the rooms upon request (the paper didn’t fold, but simply moved), oversized letterpress machine letters line the wall behind the concierge, and even the hotel’s convivial bar and lounge, INKWELL, is fittingly located in the same spot as the paper’s former local newsroom. For dinner, visit the hotel’s restaurant Union, where executive chef Josh Berry partners with farmers and fishermen across New England to source the freshest ingredients. The menu changes based on the season, but in the summer be sure to try the lightly fried zucchini flowers, tri-tip with garlic scapes and oyster mushrooms, and roasted wax beans.

Photos: Jeffrey Stevensen / Chebeague Island Inn; Irvin Serrano Photography / Press Hotel


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