Overview

Portland is Maine's largest city: Almost one-quarter of the state population lives within the greater metro area. Set on a peninsula that stretches into Casco Bay, Portland is a sophisticated coastal city with a working waterfront, but it also has its share of nearby beaches and lighthouses.

Fittingly, Portland has many of the enjoyable things, minus the hassle, that a big city can provide—a healthy arts scene, stylish restaurants, a respected symphony, the world-class Portland Museum of Art, minor-league baseball and ice-hockey teams, a slew of galleries and boutiques, and a collection of stately homes built by the city's wealthy families.

A downtown Portland renewal effort over the past few decades has reclaimed treasured Victorian-era buildings, refitted the gas lamps along the cobblestoned streets in the Old Port Exchange (known to locals as the Old Port) and sparked civic pride among residents.

Geography

The city is centered on a peninsula that protrudes into Casco Bay. From the water, Portland rises onto hillsides that offer views of nearby residential islands to the east and the mountains in neighboring New Hampshire to the west.

Commercial Street runs along the southeastern edge of the peninsula, lining Portland's waterfront and forming one border of the historic Old Port, perhaps the city's most popular tourist destination. Just a tad farther inland, close to the geographic center of the Portland peninsula, is the downtown area known as the Arts District, which extends along Congress Street.

History

Several early attempts to create settlements on Portland's site failed, beginning in 1624 with a small Casco Bay colony. Its mastermind, Christopher Levett, returned to England and wrote a book extolling the region—perhaps Portland's first example of real-estate hype. A trading post, dubbed Falmouth, was established in the area in 1632, but by the end of that century the settlement had been destroyed twice by local Native Americans. (The modern town of Falmouth is just north of Portland.)

The town thrived as a British lumber and shipping center until the Revolutionary War, when it was flattened by a British bombardment in 1775. The survivors renamed the town Portland and rebuilt it into a commercial port and shipbuilding center, drawing on Maine's vast timber resources.

In the early 1800s, many shipbuilders turned to trade, building schooners that ferried granite, timber and fish all down the East Coast—for a time Portland rivaled Boston as a port. But a celebration got out of hand on 4 July 1866: A firecracker tossed into a shipyard sawdust pile ignited a conflagration that leveled most of the city, leaving 10,000 people homeless. Portland, wealthy and resilient, again rebuilt—this time in a striking Victorian style—and once more became a flourishing commercial port.

The city emerged from a statewide economic decline in the 1970s when it was discovered by young professionals anxious to flee large cities for a simpler, yet urban, life. Not only did they help create a new economic base for Portland in banking, telecommunications and service industries, but they also brought with them a taste for cultural offerings, fine cuisine, shopping and enthusiasm for historic preservation. Although minorities are still only a small percentage of the population, in recent years the city has seen an influx of immigrants from Africa and eastern Europe.

Sightseeing

The highlight for most visitors is a stroll through the Old Port—a five-block district of cobblestoned streets, brick sidewalks and restored buildings from the 1800s. Bookstores, antiques shops, galleries, specialty shops, cafes and restaurants make the area a pleasant place to spend an entire day. Architecture buffs who look up above street level will be treated to views of slate mansard roofs, Gothic windows and Queen Anne towers.

You'll find historic dwellings outside of the Old Port, as well. There's a particularly strong collection on the Western Promenade, an area of elegant Queen Anne, Maine shingle and colonial-revival houses. Congress Street, between Monument Square and High Street, is known as the Arts District. The centerpiece of the neighborhood is the Portland Museum of Art, though the respected Maine College of Art (MECA), various galleries, shops and cafes line the street and add to the culture of the area as well. Walking through this district, you'll be amazed to find how much art surrounds you—in galleries, restaurants, on the street (in summer) and even on public walls in the form of murals.

Look for the Downtown District Guides, recognizable by their outback hats and purple shirts. They walk the streets in the summer and early fall, armed with directions, suggestions and free maps. The success of the First Friday Art Walk program is yet another testament to the strength of the city's art scene. On the first Friday of every month 5-8 pm, free self-guided tours of dozens of galleries, museums and other venues are scheduled.

Finally, the Maine seacoast is always an attraction in itself. In the summer, whale-watching tours and fishing and sailing excursions are popular. You can also enjoy the city's scenic shoreline from several vantage points. For the most panoramic views, try the venerable Portland Observatory. If you prefer not to climb the observatory's 103 steps, the Eastern Promenade's Fort Allen Park is another good place to view sailboat-dotted Casco Bay and its islands.

Remember that a number of Portland's attractions, including certain historic houses and museums, scale back their days of operation in the nonsummer months. Call ahead if you're planning a visit then.

Nightlife

Portland's nightlife is varied, with a little of everything—dark taverns offering house-brewed ales, swanky martini lounges and even a few throbbing dance halls—but where it really shines is in its wealth of live music. It's hard not to find a new local act or a native long-time favorite setting up the stage on any given night, all year long. And there's no specialty there; you'll hear funk, blues, metal, folk and a blessed mix of each, which is unusual in such a small city. Your best bet is to walk around the Old Port or the Art District areas—chances are you'll stumble across something close to what you're looking for.

Many Portland spots combine dining and entertainment: A number of restaurants invite local musicians to entertain patrons with no cover charge, and most bars have dining areas.

Dining

Portland dining has undergone a revolution, making the city one of the best in New England for inventive meals drawn from outstanding local fish, meat, cheese and produce. Chefs have cultivated strong relationships with the state's many organic growers and artisanal food producers—and even professional foragers who gather such foods as wild mushrooms and fiddleheads, an edible fern available in early spring. Whether you opt for an intimate bistro or something more upscale, you'll be encouraged to enjoy a relaxing evening at relatively reasonable prices.

Almost every restaurant makes good use of the bounty of fresh seafood available in this busy commercial fishing port. In addition to the region's renowned lobsters, local fishermen bring in large catches of haddock and halibut. Salmon, smelt, mussels, clams and Maine peekytoe crab are also farmed extensively along the Maine coast. Establishments specializing in seafood run the gamut from casual shacks to elegant linen tablecloth affairs. Also look for a variety of international cuisine such as Japanese, Thai, Indian and Irish. Several restaurants are known for their vegetarian menus.

The Old Port, Commercial Street (the waterfront) and the Arts District are all populated with restaurants. Mainers tend to dine early, with restaurants starting to fill by 6 pm. The crowds thin out after 8 pm, except on weekends. It's always a good idea to call ahead for reservations, especially during the summer, and keep in mind that many of Portland's restaurants close on Monday. Also, smoking is not allowed in Portland bars or restaurants.

Expect to pay within these guidelines for a meal for one, not including drinks, tax or tip: $ = less than US$10; $$ = US$10-$20; $$$ = US$21-$50; $$$$ = more than US$50.

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