Portland is a place where plain old Maine industriousness meets the worldly tastes of the city's newest residents—ad executives, Internet entrepreneurs, Polartec-vested boatbuilders—who have left the big city for a simpler life. There are surprises here, such as the world-class Portland Museum of Art, now showing an exclusive Picasso retrospective, and cocktail lounges whose patrons look as if they could be in an L.A. club. You may need to remind yourself that this is Maine.
did you know?
Second most common language after English: Khmer
Average cost of a house: $126,690
What's on tap: a summer ale from Stone Coast, one of Portland's six microbreweries
Average summer temperature: 75 degrees
What's on the horizon: a controversial $20 million docking facility for those really big cruise ships (the QE2 already stops here)
native sons and daughters
On the eastern edge of the Old Port District, you'll find a square called Gorham Corner (a sign reads HERE SETTLED IRISH IMMIGRANTS IN 1840) with a bronze likeness of film director John Ford, a Portland native, smoking a pipe atop a mound of beach stones. Born Sean Aloysius O'Feeney in 1895, Ford went on to direct classics like The Quiet Man and The Grapes of Wrath. Across the street is the Brian Boru Public House (57 Center St.; 207/780-1506), where County Kildare native Justin O'Reilly pours a perfect pint of stout.
Related: The 10 Best Lobster Shacks in Maine
The intersection of Congress and State Streets downtown is dubbed Longfellow Square: a statue there shows the poet Henry Wadsworth Longfellow settling down with a newspaper. His poem "My Lost Youth" is about growing up in Portland, where "a boy's will is the wind's will." Nearby is Cunningham Books (188 State St.; 207/ 775-2244), which has a collection of works by Mainers. Pick up Mary C. Jane's children's tale Mystery in Longfellow Square.
food to go
Portland's newest symbol of rejuvenation is the Portland Public Market (25 Preble St.; 207/228-2000). Like a family hearth for the entire city, this indoor market's fireplace of Deer Isle granite rises to a vaulted ceiling supported by 40-foot fir beams. Merchants at the $6 million urban food mecca take the "locally made" motif to an extreme: there's Portuguese corn bread made with Maine-grown organic wheat; cheese from the Nubian dairy goats of Waldoboro, Maine; salmon sausages; even elk fillets, pitched as tasting "the way beef used to." Stop by the Harbor Fish Market (9 Custom House Wharf; 207/775-0251) for seafood, both fresh (lobsters, crabs, cherrystones, littlenecks, oysters, shark, flounder, monkfish) and smoked (whitefish, trout, mackerel, shrimp). Aurora Provisions (64 Pine St.; 207/871-9060) is stocked with well-chosen wines, breads, cheeses, take-out meals—there's even a café. It's the place to find the ultimate summer pies for a picnic (try the strawberry-rhubarb or blueberry-peach; it's wise to order a day ahead).
The former banana storage room at the Carr Brothers' Produce Co. is now the Wine Bar (38 Wharf St., upstairs from the Café at Wharf Street; 207/773-6667). Sit in a stuffed armchair and have the country pâté with cornichons and Dijon mustard alongside a glass of St. Francis Cabernet. Úna Wine Bar & Lounge (505 Fore St.; 207/828-0300) is certainly the only cocktail lounge in Maine to have flying saucer-like stools and a bar that resembles a river of crushed green glass. The deep wine list makes it easy to complement appetizers such as sardines or spinach and Parmesan in phyllo. This is the place for Portland fashionables—say, an independent filmmaker on a date with a graphic designer—to preen; it's dark and cool and perfect for a summer cocktail. If you want something salty and brassy, stop by J's Oyster (5 Portland Pier; 207/772-4828). This local hangout is worth a visit if you can tolerate the smell of fish. A good storm draws a boisterous crowd. You might hear a bartender complaining that her husband's boat hasn't come in, or a patron inquiring as to where "Steve the Greek" is drinking tonight.
take a real look at portland documentary-style
Salt (110 Exchange St.; 207/761-0660; open Wednesday and Friday 2-6, Saturday 10-1) This center for documentary studies shows work by students who come from around the country to write about and photograph such subjects as the Portland Boxing Club or life on the Casco Bay Islands.
where to stay
Pomegranate Inn 49 Neal St.; 800/356-0408 or 207/772-1006; doubles from $145. The contemporary art collection alone would separate Isabel Smiles's Italianate house from Portland's other B&B's. Add the carriage house with its garden suite, and wine or tea served to guests upon arrival, and you have an experience that is irresistible: book several months ahead for summer or fall.
Percy Inn 15 Pine St.; 888/417-3729 or 207/871-7638; doubles from $99. Owner Dale Northrup, Portland native and travel scribe (he has written guidebook hotel reviews for two decades), did a gut renovation of this Federal-style house in the West End. Stashed in the rooms are the little touches he misses when he's on the road: fruit for midnight snacks, a trundle bed for an extra guest, Scrabble for rainy nights. Try the Longfellow Suite, with its Mexican-tiled study.
Inn on Carleton 46 Carleton St.; 800/639-1779 or 207/775-1910; doubles from $135. This restored 1869 Victorian on the Western Promenade is true Maine—claw-foot tubs, blueberry pancakes—tempered with marks of convenience: air-conditioning, a short walk to downtown. The best time of day on the promenade is sunset. That's New Hampshire's Presidential Range the sun drops behind.
The Danforth 163 Danforth St.; 800/991-6557 or 207/879-8755; doubles from $165. Whereas most of Portland's guesthouses are on the western side of the city, the Danforth is set above the Inner Harbor wharves. Rooms have working fireplaces and high ceilings with original crown moldings. Guests shoot pool in the billiard parlor, or watch their ship come in from the widow's walk on the roof.
Nothing on this street of Greek Revival and Federal houses prepares you for the over-the-top exuberance and grandeur of the Victoria Mansion (109 Danforth St.; 207/772-4841). Built in 1860, the Italianate brownstone palace was the summer residence of New Orleans hotelier Ruggles Morse, who grew up poor in Leeds, Maine. A pioneer in the luxury-hotel business, Morse brought his work home: French gasoliers, a Turkish smoking room with Islamic motifs, Italian frescoes painted on every wall, trompe l'oeil everywhere. Decorated by Gustave Herter of the famed Herter brothers (six pieces created for the mansion have been exhibited at the Met in New York), the house represented the best of Europe brought to the American city that's closest to the Continent.
maine cottage industry
For Maine-made pottery, such as a set of salt-glazed bowls, seek out Clay City/Monroe Salt Works (551 Congress St.; 207/761-2707) in the arts district, across from the L. L. Bean outlet. If you're looking for something less sturdy, try the Stein Gallery (195 Middle St.; 207/772-9072), which shows the work of 95 glass artists, ranging from the functional (vases, jewelry) to the purely decorative (who could resist a purple glass "exotic plant" the size of a turkey?). On Portland's trendiest shopping drag, both Gallery 7 (49 Exchange St.; 207/761-7007) and Abacus (44 Exchange St.; 207/772-4880) have Maine-made woodwork, pottery, jewelry, and textiles.
Street & Co. 33 Wharf St.; 207/775-0887; dinner for two $50. Mediterranean-style dishes are served in a brick-walled room with copper-topped tables and herbs dangling from the ceiling. The perfectly flaky bluefish, served with sugar snap peas, is delicious.
Fore Street 288 Fore St.; 207/775-2717; dinner for two $60. This is another venture of Street & Co.'s Dana Street, in an old warehouse where tanks were repaired during World War II. It's big, hip, and hearty: dishes such as the three-inch-thick spit-roasted pork loin are so sought after that it's a good idea to make reservations two weeks in advance.
Perfetto 28 Exchange St.; 207/828-0001; dinner for two $65. The melon green walls, lava lamps, and black-tiled bar seemed too far-out for Portland when the dining room opened five years ago, but now it's the mainstay of the restaurant scene. Go for the baked sweet native haddock with sticky rice and asparagus coulis.
Aubergine Bistro & Wine Bar 555 Congress St.; 207/874-0680; dinner for two $52. Everything here is checkered in black and white: the floors, the napkins, the waiters. Try the brioche-crusted trout fillet.
Harraseeket Inn 162 Main St., Freeport; 800/342-6423 or 207/865-9377; brunch for two $34. Take the 15-mile drive to Freeport to indulge in seafood ragoût or crêpes stuffed with lobster in a dining room that overlooks English-style gardens. Then walk it off at Freeport's 110 outlet stores.
portland island life
The archipelago of glacial islands in Casco Bay were nicknamed the Calendar Islands because some groggy explorer counted 365 of them. In reality there are 180 Casco Bay Islands, many inhabited by gulls and cormorants. Some of the islands have intriguing names such as Junk of Pork (what it looked like) and Pound of Tea (what it sold for), but the three to visit are Peaks Island (the closest to Portland), Long Island (the most beautiful beach), and Great Chebeague Island (the one with the old-style summer hotel).
The best way to see the islands is to take the Casco Bay Lines' Mailboat Run (Commercial and Franklin Sts.; 207/774-7871), a three-hour narrated tour. Steaming off on the bumblebee-colored Maquoit, you can look back on Portland's red-brick Old Port. You'll probably pass a Russian container ship called the Indropiou, and as you approach one of the islands you're likely to see kids roll down on skateboards to meet the ferry and help Mom haul home groceries.
Peaks Island (population 1,200 in winter, 4,500 in summer) is just a 20-minute trip from Portland. The ferry unloads near Jones Landing (207/766-5542), a restaurant whose porch is packed in the summer with diners wearing lobster bibs and tapping their feet to live music—swing bands, jazz groups, even the Portland Symphony. Rent a tandem bike from Brad Burkholder at Brad's Recycled Bike Shop (take a left from the dock; 115 Island Ave.; 207/766-5631).
Less populated is Long Island, known for a protected, white-sand cove called Singing Sands Beach. From the ferry landing, it's a 15-minute hike.
Most of the islands' summer hotels have long since burned to the ground or fallen into disrepair. The one remaining is the Chebeague Inn (South Rd.; 207/846-5155; doubles from $90) on Great Chebeague Island, one of the last stops on the tour. Its 150-foot-long wraparound porch overlooks the ocean in back and a nine-hole golf course in the front. This place is at the far end of the island from the Casco dock, but innkeeper Dick Bowden runs a limousine service for guests. The hotel also has the best restaurant on the island, serving seafood bought daily on the docks.