This quirky city was once known, fittingly enough, as ''Quack." Examples of its pleasure in things odd are everywhere. Monument Square, in the heart of downtown, is actually a triangle. The famous Casco Bay Bridge doesn't span any part of Casco Bay. (It crosses the Fore River.) The area near the local sewage treatment plant provides some of the best bird-watching in the state. And the city is home to what must be the only topless doughnut shop in the country.
With a population of 64,249, Maine's largest city is concentrated in a small geographic area, and it has always had a spunky, creative, somewhat wacko charm that endears it to other Mainiacs, while also setting it apart.
Its population is younger, hipper, and more liberal than elsewhere in the state. Public buses here have bicycle racks.
It's also more diverse. According to the last census, almost 9 percent of Portland's population is nonwhite, compared with 3 percent in the state. Officials say 51 languages are spoken at Portland High School. Mayor Jill Duson (whose term ends this month) isn't just the first black female mayor in the state but also only the second black woman ever elected to any office in Maine, she says.
Portland is so different from its neighboring communities that less than a year ago an issue of Down East magazine asked: Is it really part of Maine? Editors noted that all five Green Party candidates in 2004 elections came from districts in Portland, and one of them won. On issues like gun control, gay rights, hunting, and environmental politics, the magazine observed, Portlanders hold significantly different views from voters in the rest of the state.
Portland is home to the state's biggest symphony, top art museum, its only professional sports teams, and its largest concentration of restaurants. In a state almost without skyscrapers, the few high-rise buildings clustered along Congress Street, Portland's main thoroughfare, are as close as Maine gets to a downtown financial district. Although Augusta is the capital and legislative center, the state Supreme Court and the largest concentration of lawyers are here.
According to Guinness World Records, Portland is the only city in the country with one street on which a person could satisfy all his or her educational needs. A preschool, two elementary schools, a middle school, two high schools, and a branch of the University of New England are on 2-mile-long Stevens Avenue.
Some people have both their winter and summer homes in Portland. They spend winter on the mainland and summer on one of several Casco Bay islands technically inside the city limits: Peaks Island, Great Diamond, Little Diamond, Cushing's and Cliff islands among them. (For a quirky island tour, you can ride the mail boat as it delivers letters, freight, and passengers to the islands.)
The city houses at least two oddball, one-of-a-kind museums: The Umbrella Cover Museum (on Peaks Island), displaying all sorts of umbrella covers, humble and exotic, from around the world; and The Museum of Cryptozoology, dedicated to animals whose existence has not yet been confirmed, such as Big Foot, assorted sea monsters, and the like.
Especially in the historic Old Port, the city boasts a large assortment of one-of-a-kind shops and many distinctive galleries. Among them is SPACE, which sponsored an event in September that included rolling a huge swath of sod down Congress Street, making it an impromptu park, and turning dumpsters into theaters for puppet shows, dance, and other performances.
Other art openings take place in similarly unconventional settings. Just a few weeks ago, a hair salon called Head Games hosted the opening of an exhibit by photographer Arthur Fink. Fink said he was drawn to the salon as a place to show his work because of its light and space, and he likes the idea of new art constantly appearing throughout the city in surprising places.
For Portlanders, Fink said, being quirky ''is a way of staying fresh and alive, and making new connections."
Now through mid-February, visitors also can see the arresting sculptures of Pandora LaCasse, which she describes as ''little oases of light and cheer to warm the dead of winter." An abstract sculptor, LaCasse wraps trees, poles, and homemade forms in strings of colored lights all over the city. In a park at Middle and Exchange streets, turquoise ovals hang from pink trees. On Congress Street, fanciful orange and red megaphones cluster in front of the Time and Temperature Building. On Commercial Street by the harbor, blue and green spheres protrude from some shops, as if they were big water bubbles.
Portland's quirkiness is long-standing. Right from the start, it developed a reputation as a liberal, free-thinking place.
Maine was settled in part by people who objected to what they considered the Puritanical, restrictive ways common in Massachusetts, and they seem to have gravitated particularly to Portland, established in 1786. When Maine became the nation's 23d state in 1820, Portland was its first capital.
One guidebook describes Portlanders in the 1800s as ''boozehounds" and says waterfront laborers routinely took ''grog breaks" in the mornings and afternoons. Munjoy Hill, in the east end of town, was known as ''Mount Joy Hill," in honor of the prostitutes who frequented the area.
One of the city's towering oddities is the Portland Observatory, which looks like a lighthouse in a distinctly urban setting on Congress Street. Sandwiched between the Portland Free Methodist Church and the Fire Department and across from Colucci's Hilltop Superette, it is actually an old signal tower, erected in 1807 as a communication aid for ships heading to port.
Over the years, several well-known distilleries have had headquarters here, including McGlinchy's and the John Morgan Brewing Co., and the city remains famous for its microbrews such as Shipyard, Allagash, Geary's, and Gritty McDuff's. It has a flourishing nightlife, with several nightclubs and saloons where you can hear local bands. So many bars are crowded into the Old Port that a person can bar crawl without having to drive.
Most of Portland's attractions are concentrated on its peninsula, a compact area about three miles long and less than a mile wide. Still, outlying areas bear exploration as well. Within the city limits are at least two waterfalls and a network of about 30 miles of trails that meander around the Back Cove, along the Fore River, around the harbor, and through the Maine Audubon Sanctuary, which has two important sites in the metro area. Bird-watchers especially enjoy a trail that passes the city's sewage treatment plant, where ospreys have erected a huge nest on an abandoned railway trestle, and where you can sometimes see a bald eagle or exotic sea gulls.
Just north of the city limits but well within Metro Portland is Mackworth Island, a good place to witness the local pleasure in fun and fantasy. Given to the state by Percival Proctor Baxter as ''a sanctuary for wild beasts and birds," the island now is home to the Governor Baxter School for the Deaf, but a 1 1/4-mile trail around the perimeter is open to the public. The path passes a pet cemetery (the final resting place of 13 Irish setters and one horse); a ''listening tree" said to be able to understand the sign language of the hearing impaired as well as entreaties from more conventionally speaking people; and an extensive ''community village for fairies," where children are invited to build fairy homes out of natural materials.
On a recent day, Delaney Derrig, 7, a second-grader in nearby Westbrook, was beginning construction of one of these little twig dwellings under the watchful eye of her grandmother. She said fairies are drawn to the area ''because there are homes for them. They need somewhere to live."
Portland also is a restaurant town. Many locals proudly claim it has more restaurants per capita than anywhere in the country except San Francisco. One list shows 187 restaurants in Portland, or one for every 343 people.
City regulations do not allow food chains downtown, and the restaurants can be as quirky as the city itself. You will never pay more for less food than at Bandol's, where the portions are so tiny as to be laughable. (A recent entree of braised veal on a potato pancake with chanterelle mushrooms measured no more than two inches in diameter, including the sauce.) Hugo's, the trendiest spot in town, with somewhat bigger portions and considerably better food, offers cod tongue tempura.
Street & Company, the favorite of many locals, may be one of the few restaurants in the country that serves no meat; it's strictly about seafood. Silly's, a popular cheap eats joint near Munjoy Hill, sells an avocado milkshake, which is better than it sounds. Joe's Boathouse boasts a local favorite known as ''The Zook," a wrap with fresh chicken, tomato, onion, and homemade caper mayonnaise.
Sitting at Joe's, you can watch the comings and goings in the outer harbor and gaze upon another local oddity: Fort Gorges. This looks like a huge granite square floating in the bay with some grass on top. In fact, it's an old fort built on Hog Island in 1858 to defend Portland Harbor. However, no shot ever was fired from it.
The topless doughnut shop, part of an adult center called Platinum Plus, looks more like a plush nightclub lounge than a morning breakfast spot. But it's open Monday through Saturday, 6-11 a.m., and it does sell doughnuts, $1.50 apiece. They don't make their own, though, a young blonde woman called ''La Bomba" told me when I finally mustered the nerve to go in. When I asked who does, she giggled and said, ''It's a secret."
Contact Judith Gaines, a freelance writer in Maine, at email@example.com.