Robin Blair Riley
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A Perfect Weekend in Portland

A gutsy little city baits visitors with a second wave of pioneering chefs and cool designers

By Norman and Stephanie Vanamee

July 28th, 2009

There are a million ways to vacation in Vacationland, but like a lot of people who make yearly trips to the state of Maine, we had fallen into a rut. Every summer, we embarked from New York City on a 6-hour drive, which landed us in a family beach house where we spent our days untangling nieces and nephews, plunging into the frigid ocean, and debating when to have the big lobster dinner. Not particularly original, but as far as annual getaways go, relaxing and loads of fun.

In recent years, however, we added another element to our routine: a regular pilgrimage to Portland. Maine's largest city is more than a decade into a well-documented culinary boom, and a second wave of upstart chefs is keeping the scene fresh. A sophisticated mix of boutiques incubate adventurous design, some of which have gained a national following. The Portland Museum of Art shows off work by Maine’s adopted sons, Winslow Homer, Edward Hopper, and Andrew Wyeth, and the first Friday of every month finds some 30 galleries hosting wine-and-cheese receptions for an art walk. At night, the bars along Fore Street and the lounges of the Arts District are thick with locals sipping pints of Shipyard to the thrum of live music, letting off a youthful buzz redolent of that other Portland.

Not bad for a city of 64,000.

Our side trips have become so enjoyable that this year we are even contemplating risking the family’s wrath and skipping the beach house altogether in favor of a weekend of eating and shopping our way through Portland.

Destroyed four times (twice by Wampanoag Indians, once by the British, and once by fire), Portland has a long history of reinvention. Through centuries of booms and busts, enterprising locals have made fortunes manufacturing everything from ship masts to glassware and prosthetic limbs. When the bottom dropped out of a market, as it often did, they tried something new (the city seal shows a phoenix rising from the ashes). Over the past few decades, that something new has been tourism, which has thrived and with good reason: Portland has a modern airport with nonstop flights to hubs around the United States, a walkable revamped waterfront called the Old Port, and lovely sand beaches just 8 miles to its south.

Yet a scrappy creative energy still persists here (that belies the lobster kitsch all over), along with the sense of small-town camaraderie that undoubtedly waters the many grassroots endeavors.

View our Portland Slideshow by photographer Robin Blair Riley for glimpses of the Pine Tree state's most sophisticated city.

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