During winter, the cold waters of Casco Bay give the wind a mean, briny edge as it whips through Portland. But even on the bitterest days, you’ll find hearty fans waiting outside Duckfat’s door for a cone of golden frites and a crisp, decadent meatloaf panini. A few blocks west, you’ll see the hungry line up outside of wood-fired Fore Street to score the day-of reservations handed out at 5 p.m. When the cold bites here in one of the country’s most restaurant-dense cities, Portlanders bite right back.
The East End’s up-and-coming Washington Avenue is a perfect entrée into this gastronomic boomtown. Start with a study of Maine versus Massachusetts oysters at the Shop, a new raw bar by the folks behind Duxbury’s Island Creek Oysters. Then pick your next stop by your drink of choice. Steps away, there’s the wine bar Drifters Wife, a tasting room dedicated to Oxbow’s Belgian-style brews, and another pouring Hardshore Distilling Company’s floral gin. For dinner? Cross the street for Maine uni spoons and brothy duck hot pots at Japanese-style gastropub Izakaya Minato.
Once you’re ready to check in for the night, consider the Press Hotel, in the former home of the Portland Press Herald downtown. Or try the Danforth Inn, a 19th-century mansion with nine luxe rooms in the West End’s historical district (be sure to nab one with a fireplace!).
The next day, ease into morning over a cup of espresso and a hunk of coconut-spelt teacake at Tandem Coffee + Bakery, a former gas station turned airy café. It’s all the fuel you’ll need for an excursion to Portland Flea-For-All on Congress Street, where more than 60 vendors hawk vintage goods, or to the Portland Museum of Art, which showcases an extensive Winslow Homer collection.
Still hungry? Go ahead and wander until you find an inviting spot—in this culinary hotbed, the next big thing is never far away.
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Two-hour drive from Boston
Score deals on duck boots and flannel at L.L. Bean’s vast complex of stores, a quick drive away in nearby Freeport. Maine Beer Co.’s tasting room is also there, so stop in for a pour of Peeper en route to the outlet stores.
More cold-weather escapes from our Boston Traveler 2018 issue.
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