Portland delivers on the Maine icons but good. Lobster boats bob in the harbor. An L.L. Bean outlet can be found downtown. You might even spot the occasional stray moose. But Maine’s largest city (pop. 65,000) is more than postcard fodder. It has a burgeoning arts district anchored by the expansive Portland Museum of Art. A group of local-minded chefs have helped put the city’s dining scene on the frontlines of the farm-to-table movement. Add location: Sitting smack between Maine’s sandy southern coastline and the dramatic, rockbound peninsulas of the mid-coast, this seafaring city offers visitors access to the best of both coastlines, as well as the half-dozen or so spruce-covered islands reached by regular ferry service. In short, it’s easy to see why Portland consistently tops national surveys that ask people to name the best places to live, play—and, increasingly, where to eat.
Although the area was settled in 1633, the Great Fire of 1866 shaped today’s Victorian-influenced, predominantly brick cityscape. The downtown peninsula, an elbow defined by the Fore River, Portland Harbor, Casco Bay and Back Cove, is the city’s hub. Congress Street, Portland’s spine, connects the East End with the West End, bisecting the Arts District and climbing Munjoy Hill to the rejuvenated Old Port area. On the waterfront, old salts and young professionals mingle over breakfast at Becky’s Diner and the Porthole. All in all, it feels more small town than big city, with a sole 16-story “skyscraper” and a glimpse of the sea around almost every corner.
ART AND HISTORY
The top spot to get your bearings is the Portland Observatory (138 Congress St.; 207-774-5561; portlandlandmarks.org; $7), the last remaining maritime signal tower in the country. Captain Lemuel Moody built the octagonal red tower on Munjoy Hill in 1807 to track activity in the harbor. Thanks to a $1.28 million restoration effort, it’s now a National Historic Landmark. Climb the 103 steps to the orb deck for sweeping views extending over Casco Bay’s islands to the open ocean, and, in the other direction, beyond the suburbs to Mount Washington.
Stay in the history mode with a tour of the Victoria Mansion (109 Danforth St.; 207-772-4841; victoriamansion.org; $13.50). Magnificently ornamented in the Italianate style, this National Historic Landmark is considered among the finest remaining pre-Civil-War-era dwellings of its type. Inside, it drips with Victorian opulence, from the stained-glass ceiling window to the frescoed walls, the trompe l’oeil ceilings and freestanding mahogany staircase.
Bridging the centuries is the Portland Museum of Art (7 Congress Sq.; 800-639-4067; portlandmuseum.org; $10), the gem of the downtown arts district. Works by American and European masters are exhibited in three architecturally distinguished buildings. Maine-related art is arguably the museum’s strongest suit: There’s a substantial collection of works by Winslow Homer, including his first oil painting. The artist lived the latter part of his life just 12 miles south of the museum in Prouts Neck. The museum is currently in the middle of an $8.3 million fundraising drive to restore Homer’s studio there.
Next door, at the Children’s Museum of Maine (142 Free St.; 207-828-1234; kitetails.com; $8), kids can play in the woods, captain a lobster boat and pretend they’re pirates. On the third floor, the camera obscura exhibit delivers spectacular views of Portland without a window.
With the museums as anchors, arts are leading the revival of Congress Street. Once the city’s commercial hub, it began sliding in the 1970s, when department stores moved to the suburbs. Now it’s percolating again, with eclectic shops, galleries, the Maine College of Art and an L.L. Bean outlet leading the way.
During the First Friday Art Walks (firstfridayartwalk.com), held on the first Friday evening of each month, galleries coordinate openings, restaurants offer specials and the Museum of Art is open at no charge. Combine hobnobbing with the arts crowd with a sunset drink at the Top of the East, the window-walled lounge topping the Eastland Park Hotel.
The arts aren’t all visual. Despite its relatively small population, Portland supports a professional symphony orchestra, an Equity theater, and even a summer opera company. (The company is celebrating its 15th anniversary this summer with music from past productions.) Various other organizations present concerts, films and festivals throughout the city, including free events at places like Tommy’s Park, in the Old Port.
Portland’s original urban revitalization project, the Old Port, remains one of the city’s biggest draws. Walking the brick sidewalks and cobblestone streets is the best way to appreciate the area that flows off Congress Street to the waterfront. Or take a guided tour with Greater Portland Landmarks (portlandlandmarks.org; $7). Guides point out historic sights, explain how ships once docked where cars now pass, and describe how near-destitute buildings were rejuvenated to house tony boutiques and restaurants.
Rumor has it that Portland is second only to San Francisco in the number of restaurants per capita. That’s easy to believe; what’s more surprising is their quality and variety. Choices range from french fries and pizza to sweetbreads and lobster, from cheap takeout to multi-course fine dining. Though the state as a whole is one of the least ethnically diverse in the nation, Portland still has a multicultural nature, seen in its array of ethnic eateries: African, Polish, Greek, Vietnamese and more. Of course, seafood is plentiful. Marrying the city’s seafaring heritage with food is DiMillo’s Floating Restaurant, housed in a converted ferryboat.
With the ocean at the front door and farmland out the back, Portland is on the frontlines of the farm-to-table and fresh-and-local movements. And by most reports, no one deserves more credit for this than Sam Hayward, the James Beard Award–winning chef of Fore Street. His 30 years of support (and counseling) for local food producers means other city chefs now enjoy a vibrant array of artisanal ingredients, be they mussels or haricots verts. In short, Hayward’s efforts have helped guarantee that he’s no longer the only starfish in Portland’s sea. Also receiving national kudos are Rob Evans of Hugo’s, and Steve Corry of 555. Rising stars include Evangeline for French classics, and Bresca, a vest-pocket Mediterranean spot. Back Bay Grill, always one of the city’s top tables and perhaps its most elegant one, shouldn’t be overlooked.
East of Franklin Street, at the base of Munjoy Hill, is an emerging foodie neighborhood. Its Italian roots still flavor Micucci’s grocery, where Stephen Lanzalotta uses classic brick-oven baking techniques to produce some of the city’s best bread and Sicilian-style pizza. A few doors up India Street is Two Fat Cats Bakery, a sibling of Fore Street Restaurant, which has perfected pies and cookies.
When it comes to perfection, no one disputes that Duck Fat reigns as the king of french-frydom. Chef Rob Evans, owner of the acclaimed Hugo’s Restaurant, also operates this casual order-at-the-counter bistro. Here the Belgian fries are double-fried in, yes, duck fat, then served in a paper cone with a choice of sauces, including truffle ketchup. Save room for a shake, made with ice cream from Smiling Hill Farm. Walk or bike it off on the Eastern Promenade Trail, which edges the shoreline and connects to miles of other trails lacing the city and suburbs.
LOBSTER AND LIGHTHOUSES
Beyond the waterfront, islands beckon. Ferries and excursion boats weave between the spruce-fringed dots, passing winking lighthouses and abandoned forts, lobstermen hauling traps and seals basking in the sun. On a breezy day, nothing beats a sail aboard a historic windjammer with the Portland Schooner Co. (207-766-2500; portlandschooner.com; from $35).
Connecting the islands with Portland are the ferries of Casco Bay Lines (207-774-7871; cascobaylines.com; from $8.20). The Mailboat Run scenic cruise dishes up an island sampler as it hopscotches around. If a single-island immersion will suffice, board a ferry to Peaks Island to have a walkabout and lunch at the Cockeyed Gull.
For an authentic taste of the seafaring life, the opportunity to catch your own dinner, and water-cooler bragging rights, join lobsterman Tom Martin aboard Lucky Catch, his 37-foot lobster boat (888-624-6321; luckycatch.com; from $25). If inclined, you can don oilskins and assist in hauling, emptying and baiting the traps. Best part: Any lobsters caught can be purchased for boat price, and a nearby restaurant will prepare them for a small fee. How’s that for a tasty souvenir of Maine?
Chef and co-owner Sam Hayward won the
2004 James Beard award for best chef in
the Northeast. 288 Fore St.; 207-775-2717;
dinner for two, $90*
STREET & CO.
Seafood and only seafood is served at
this Old Port favorite, tucked away in a
cobblestone alley. 33 Wharf St.;
207-775-0887; dinner for two, $65
Rob Evans, chef and co-owner, was named
Best Chef in the Northeast in 2009 by the
James Beard Foundation. 88 Middle St.;
207-774-8538; dinner for two, $100;
eight-course tasting menu $90/person
Steve Corry, chef and co-owner, was one
of Food & Wine’s Top 10 new chefs in 2007.
555 Congress St.; 207-761-0555; dinner
for two, $70; five-course tasting menu
BACK BAY GRILL
An elegant but unpretentious fine
dining experience with excellent service.
65 Portland St.; 207-772-8833; dinner
for two, $80
Amazing fries, fabulous shakes, homemade
sodas and delicious soups, salads
and panini all emanate from Rob Evans’s
ultra-casual bistro. 43 Middle St.; 207-
774-8080; lunch for two, $22
A tiny restaurant with huge Mediterranean
flavors and spectacular desserts. 111 Middle
St.; 207-772-1004; dinner for two, $90
French bistro classics served with flair in
a setting that evokes Paris. 190 State St.;
207-791-2800; dinner for two, $100
Fresh food, fast. The seating area
includes a playroom in a former bank
vault. 83 Exchange St.; 207-321-2050;
lunch for two, $25
All-natural flatbread pizzas prepared in a
wood-fired oven and served in a harborfront
dining room. 72 Commercial St.;
207-772-8777; lunch or dinner for two, $25
DIMILLO'S FLOATING RESTAURANT
All-American fare in a renovated ferry
docked in the harbor. 25 Long Wharf;
207-772-2216; lunch for two, $30;
dinner for two, $70
390 Commercial St., Hobson’s Wharf;
207-773-7070; breakfast for two, $12
Built on the wharf, with outdoor seating,
too. 20 Custom House Wharf;
207-780-6533; breakfast for two, $15
*Prices cover a three-course meal for two, not including drinks, tax or tip, unless otherwise stated.
RCI-AFFILIATED RESORTS NEAR PORTLAND INCLUDE:
SEA MIST RESORT OF MAINE, Wells
HILLCREST CONDOMINIUMS, Ogunquit
SEACASTLES RESORT AT OGUNQUIT, Ogunquit
For more information, visit RCI.com or call:
PORTLAND HARBOR HOTEL
A 106-room boutique hotel wrapped around
a central courtyard in the Old Port.
468 Fore St.; 888-798-9090;
portlandharborhotel.com; peak season
doubles from $289
PORTLAND REGENCY HOTEL & SPA
A 95-room boutique hotel in a renovated
1895 neoclassical armory in the heart of
the Old Port. 20 Milk St.; 800-727-3436;
theregency.com; peak season doubles
INN ON PEAKS ISLAND
A six-room inn, just steps from the ferry
dock on Peaks Island, with fabulous sunset
views over Portland. 33 Island Ave.,
Peaks Island; 207-766-5100; innonpeaks.com;
peak season doubles from $250
MORRILL MANSION B&B
An Italianate townhouse renovated into
a comfortable seven-room inn with
contemporary amenities, in Portland’s
West End. 249 Vaughan St.; 888-566-7745
or 207-774-6900; morrillmansion.com;
peak season doubles from $149
INN BY THE SEA
Stylish, recently renovated 57-room
beachfront inn with cottages, spa and
restaurant, seven miles south of Portland.
Pets welcome. 40 Bowery Beach Rd.,
Cape Elizabeth; 800-888-4287 or
peak season doubles from $429
INN AT ST. JOHN
A historic 39-room hotel that delivers
a lot of boutique-hotel bang for the buck.
939 Congress St.; 800-636-9127 or
207-773-6481; innatstjohn.com; peak
season doubles from $119, including
NOTE: Information may have changed since publication. Please confirm key details before planning your trip.