Great Quirky Places to Retire

Portland is known as one of the friendliest cities for bicyclists in the country. — Photo by Jordan Siemens/Corbis

Portland, Ore.

All the accolades, popularity and rising real estate values haven’t altered what makes Portland special: The place is quirky to the core. Fueling this extended reign are, foremost, the type of people the city draws — creative, free-spirited, stridently alternative — and a well-supported slew of edgy local businesses. We’ll concede that the Keep Portland Weird campaign lacks originality (Austin launched that one first) but the sentiment pervades, and you are unlikely to feel the walls of conformity close in on you in Oregon’s largest city.

On the practical front, Portland serves up organic food in inviting cafes, proximity to coast and mountains, artsy retail stores and well-planned public spaces.

The city is divided into quadrants, with the Willamette River separating the northeast and southeast sections from the northwest and southwest. The heart of downtown is on the west side, with fabulous restaurants, the famous Powell’s City of Books, and pedestrian-friendly shopping districts.

Actually, the entire city has similar attributes. The southeast, for example, has more of a middle-class/bohemian feel, with charming old homes, packed coffeehouses and offbeat clothing stores.

Portland wins regular honors for progressiveness. The League of American Bicyclists ranks Portland as the most bicycle-friendly city in America (the city even has bicycle stoplights). The city has a high — and growing — ratio of parkland per resident, along with a robust public transit system.

The city is so progressive it inspired the self-parody television series “Portlandia,” offering residents the chance to squirm uncomfortably as they laugh, sort of, at their collective eccentricities.

For high culture, Portland fields two symphonies and many choral and chamber groups. There are large art and science museums, and a very active arts community. Portland often ranks in the top 10 most literate cities (in an annual study by Central Connecticut State University).

The recession hit Portland hard; the unemployment rate is 8.6 percent (February 2012). Oregon offers residents age 62 or older a substantial tax credit on pension income: Many older residents pay no state income taxes.

The area has an unusually high number of public universities, including a large state university campus and community college in Portland.

The concentration of physicians and specialists in Portland is above average, but the number of hospitals and beds per capita is low. Residents eat healthfully and exercise regularly and have low rates of obesity.

On the downside, the metro population swelled from 1.5 million people in 1990 to 2.2 million today. But if this is stressing everyone out, you wouldn't know it by the hap-hap-happy vibe around town.

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