Once resolutely working-class, Portland is changing fast. You can still buy fresh oysters, but now they'll shuck 'em for you
An intense revitalization effort began years ago in Portland's cobbled Old Port area, transforming it into a clutch of galleries, microbreweries, and stylish boutiques.
Today, it seems like every corner of Portland is being rehabbed, including the once-dicey Munjoy Hill. Inventive chefs in search of ultrafresh seafood and produce are hanging out shingles like mad. The result is that Portland has more restaurants per capita than any other U.S. city except San Francisco, and many serve a lot more than just lobster rolls and a good bowl of "chowdah."
Some places, thankfully, never change. For 15 years, Becky's Diner has opened at 4 a.m. to serve pancakes and eggs to fisherman. You can see what the fishermen caught at the Harbor Fish Market. You can even buy lobsters packed for travel--around $50 for four (prices are seasonal).
Portlanders love the chowder at Gilbert's and the "raw and nude" oysters on the waterfront at J's, which hasn't changed a bit since the 1970s. Any non-seafoodies should check out The Flatbread Company, a dockside restaurant that bakes organic pizzas, like its nitrate-free maple-fennel sausage pie, in an igloo-shaped wood oven. Or head to restaurant row on Middle Street for a meal at Duckfat, specializing in indulgent snacks like Belgian fries (cooked in duck fat) and panini filled with sour-cherry butter. Walk it off by trekking crosstown to the Victoria Mansion, one of the country's best-preserved pre-Civil War residences. Sea-inspired masterworks by Winslow Homer and the Wyeths hang on the walls of the nearby Portland Museum of Art, designed by I.M. Pei's architecture firm.
After a long day hoofing it around Portland's hills, treat yourself to an expert foot massage at SOAK Foot Sanctuary and Teahouse, followed by dinner at Portland's best new restaurant, 555. Run by two transplants from Napa Valley, it has a well-curated list of wines available as tasting pours. If you eat just one thing while in town, let it be the Bang's Island mussels, steamed in chive butter with pickled cherry peppers, roasted garlic, and white wine.
The West End, a historic residential neighborhood with a leafy promenade, is full of B&Bs that are great alternatives to the city's pricey waterfront hotels. Guests at the Percy Inn stay in one of seven antique-filled rooms named after poets; the narrow 1830s townhouse also features a cozy reading room with fireplace and a 24-hour help-yourself snack pantry.
For an only-in-Portland tour by water, hitch a ride with the mail boat as it makes deliveries around Casco Bay. One of the prettiest stops is Great Chebeague Island. See Mac, "the Bike Guy," at the intersection of South and North Roads, and sign out one of the sets of wheels in his front yard that he loans out for free.
If you're tempted to spend the night, reserve a room at the Chebeague Orchard Inn B&B. Neil and Vickie Taliento have been innkeepers for 15 years and have the details nailed--cut sweet pea blossoms from their garden, tubes of Tom's of Maine toothpaste, and blueberry pancakes at a farmhouse table. They'll even greet you right at the dock.