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Great Quirky Places to Retire

10 funky and artsy cities that free spirits will love

Have you always thought of yourself as someone who marches to your own drum? Or known that, deep down, you felt most at ease in funky communities filled with creative, free-spirited people?

Now that you’re thinking of retiring, it’s time to be true to your inner compass and settle in a place where “eccentric” is a compliment and where people are free to be whoever they want. Well, we’ve found 10 perfect places in the United States for people like you. For lack of a better word, call them “quirky” — towns and villages that dance to their own beat — just like you.

Whether that means an annual festival that peaks with the burning of a giant puppet, traffic lights specifically for bicyclists or four-hour barn concerts hosted by 1960s rock legends, we think you’ll find a town or two that will quench your thirst for originality. 

Of course, as with all our Great Places to Retire lists, we’ve also factored in cost of living, quality and availability of health care, and crime and safety. Nowhere is perfect, of course, but who ever said perfect was the goal? We’ll take the fun of quirky over impossible perfection any day.

Ulster County, N.Y.

Ulster County, N.Y. (population 182,493) is a funky string of artist-haven villages edged by vast swaths of bear-haven mountains. Residents occupy villages and the bears roam the 287,500-acre Catskill Mountains Forest Preserve.

Ulster’s villages are strung prettily along the Hudson River. The biggest city is Kingston (population 24,000); the second-biggest is New Paltz, about 13 miles southwest of Kingston, where the 7,000 permanent residents are outnumbered by SUNY-New Paltz’s 7,754 students. The tourism-based economy helped keep Ulster County’s unemployment rate below the national average for much of the recent recession, but at 9.1 percent it’s now slightly higher than the national average.

Of special note to retirees: Residents age 59 1/2 and older can take $20,000 a year from qualified pensions free of state income taxes, and all pensions are tax-free for retired military and government workers.

Kingston’s historic core is the waterfront Rondout neighborhood, which features brick buildings from the 1800s and a slew of restaurants, galleries and avant-garde venues like the Kingston Museum of Contemporary Arts and Deep Listening Institute, a center for poets and experimental musicians. Kingston is home to the Ulster Performing Arts Center, a restored 1927 movie palace now lit for touring acts and community productions. The area is also a foodie haven, with many small farms and artisan food makers having settled in the Hudson Valley.

The Kingston Farmers’ Market draws thousands downtown on Saturdays between May and Thanksgiving and from December to April. Off season, locals also hit the indoor Adams Fairacre Farms, which is like a farmer’s market on steroids.

Student-artists from the SUNY-New Paltz School of Fine and Performing Arts draw enthusiastic crowds, but the big ticket in town is often the Midnight Ramble concerts, four-hour parties in a barn that doubles as the Woodstock recording studio of Levon Helm, the former drummer for The Band.

For outdoor recreation, the area boasts fine golf courses, the Belleayre Mountain Ski Center, and extensive options for hiking, camping, canoeing and cross-country skiing on and around Slide Mountain. Shawangunk Ridge is world-famous for both rock climbing and the deluxe accommodations at Mohonk Mountain House. 

Crime rates here are very low. The number of doctors and hospital beds per resident is below average but big medical centers are 50 miles away in Albany. The number of smokers is above average, and so is the death rate from cancer. But many people here say that they eat healthy and get regular exercise. No word on how often that exercise involves fleeing from bears.

Austin, Texas

The question that free thinkers have about Austin, long a traditional oasis of liberal edginess, is whether or not its soul has grown staid. We think not. Originality remains a badge of pride here, as do progressive political stances (gay rights, for example), green living, large and convenient parks, and artsy festivals.

This metro area of 1.7 million, on the eastern edge of the Texas Hill Country, sprawls along Interstate 35, about 200 miles south of Dallas.  One reason Forbes magazine called Austin “recession proof” in 2008 is the job market at the University of Texas (enrollment 50,995), which attracts top talent in fields like medicine, computer science and engineering. UT joins Austin Community College (45,000 students) and Texas State’s campus in San Marcos (30,803) to anchor a young metro area that ranks among the most literate U.S. cities.

Austin’s urban design follows Complete Streets, a national network advocating shared roads usage. It is bicycle-friendly and has a high ratio of total parkland per 1,000 residents. One standout is Barton Springs, where the limestone bed of Barton Creek has been quarried to make a large natural swimming pool.  It’s an essential stop in Austin’s scorching summer.

Austin boasts excellent ballet and dance companies, the Austin Museum of Art, and UT’s Jack S. Blanton Museum of Art, the largest university art museum in the United States. But the real musical action is at Austin’s honky-tonks. Texas dance halls and bars like the Broken Spoke, Continental Club and Antone’s showcase iconic Texas musicians, including Joe Ely and Asleep at the Wheel, plus up-and-coming acts. 

Big annual events include the South by Southwest festival in spring and the Texas Book Festival in late fall, featuring hundreds of authors and panel discussions.

Crime is much lower in Austin than it is in most other Texas cities. Traffic congestion is an issue and feeds the high use of mass transit and foot and bike commuting.

The availability of doctors is below average here, and there are not many hospital beds per capita. But Austinites have low mortality from heart disease and cancer, and low rates of obesity, cholesterol problems and hypertension. Maybe abiding by the unofficial motto, “Keep Austin Weird,” also keeps the locals young.

Boulder, Colo.

Boulder’s quirky street cred suffers a little more every year thanks to the classic pattern: Dreamy locale draws lots of people, housing prices skyrocket, eccentric folks are squeezed from the core of town. But in Boulder, quirky and financially successful are not mutually exclusive. The offbeat crowd mixes well with the town’s many college kids, and they all enjoy abundant sunshine and proximity to a vast mountain playground.

The pride in originality starts at the top — Boulder’s government has partnerships with seven sister cities, including Lhasa, Tibet; Dushanbe, Tajikistan; and Jalapa, Nicaragua. From there it extends through the ranks of University of Colorado students and professors, local merchants and small-business owners — and a community of elite athletes, who live here so they can train at 5,430 feet above sea level.

The heart of town is Pearl Street, a four-block pedestrian mall lined with cafes, bars, boutiques and more. Take in a show at the Boulder Theater or tap the university's performing arts slate; in town are several art galleries and a large, well-funded public library system.

The city has used tax revenue since the late 1960s to buy land for parks. The result is the Greenbelt, a 45,000-acre oasis cocooning Boulder from Denver's sprawl. The local parks are heavily used, but there is ample room to move — and to find your slice of solitude. Even walking the leafy neighborhoods of Victorian homes and bungalows can provide a quick-fix nature lift.

Boulder County (population 294,567) includes Boulder (97,385), Longmont (86,270) and Lafayette (24,453), plus several small hamlets tucked into the mountains. The economy is diverse and strong: Unemployment is only 6.2 percent (February 2012), and the workforce includes a lot of self-employed professionals.

The University of Colorado at Boulder (enrollment 29,884) and Front Range Community College (20,000) welcome students of all ages. Boulder is one of the top-ranked metro areas in the country for the proportion of adults with a four-year college degree, and is also a nexus for alternatives in spirituality, education and medicine. Among other alternative institutes of learning, you can get degrees at Naropa University (Buddhist Studies), the Boulder College of Massage Therapy or the Montessori Education Center of the Rockies.

Boulder boasts bike lanes and paths, and mass transit is great. The county has several municipal public recreation centers with pools, basketball courts, extensive weight rooms and more. Locals, unsurprisingly, are extremely fit and healthy overall. If there's a drawback for retirees it might be that relatively few residents are 65 or older, although more move in every year.

Cape Cod, Mass.

If you think Cape Cod is a packed tourist attraction, consider that the heart of the tourist season runs only from July 4 to Labor Day. The rest of the year, this collection of towns offers quietude, seaside living and locals who appreciate — and welcome — the whimsy of artists.

There’s a long history of resident artists on the 65-mile peninsula. The playwright Eugene O’Neill and the painter Edward Hopper had houses on Cape Cod. The novelist Norman Mailer is buried here. The comedian John Belushi held and attended famously wild parties on the cape.

Cape Cod includes the Upper Cape (Bourne, Sandwich, Falmouth and Mashpee); Mid Cape, which has the biggest towns — Barnstable and Yarmouth; Lower Cape, which includes Harwich, Brewster, Chatham and Orleans; and the Outer Cape (Eastham, Wellfleet, Truro and Provincetown). Much of the Outer Cape comprises Cape Cod National Seashore.

The proportion of workers who are self-employed (think artists and consultants) is very high. A lot of residents are age 65 and older, and not many are under 35. Massachusetts gives retired public servants something extra: Most payments from public pensions are exempt from the state’s notoriously high income taxes.

A lot of Cape Codders have college degrees, and the peninsula has a large, well-funded library system. But there’s only one full-service campus here: Cape Cod Community College (enrollment 4,500). Top mariners are drawn to the Massachusetts Maritime Academy in Buzzards Bay and some of the world’s best marine biologists hang out at Woods Hole Oceanographic Institute.

You can take classes at the Cape Cod Museum of Art in Dennis, which also accepts volunteers. Cape Cod has myriad small museums and art galleries and year-round theater companies in Woods Hole, Provincetown and Wellfleet. There’s a school for painters in Provincetown and a dance academy in Barnstable.

Outdoor life here is exceptional. Bicyclists can ride the 22-mile Cape Cod Rail Trail or the 10-mile Shining Sea Bikeway. Kayakers can ply the bays, marshes and sea. Sailors can choose between the relative shelter of Cape Cod Bay and Buzzards Bay or venture out into the open ocean. And there are hundreds of miles of great beaches.

Cape Codders have a long life expectancy and low rates of obesity, cholesterol problems and diabetes. Residents are unlikely to smoke, and most locals eat healthy and get regular exercise. There are also a lot of doctors for such a small, isolated place, but not many hospital beds for 200,000-plus people. 

Cape Cod is buffeted regularly by Nor’easters and feels the occasional hurricane. That’s a good time to close the storm shutters and turn to creative indoor pursuits. 

New Orleans

New Orleans has long been known as a high-octane party town. But this is also a city of leafy neighborhoods, outdoor cafes, succulent food and perhaps the best concentration of live music in the United States.

The city has clawed back from the devastation of Hurricane Katrina — the population is 343,829 versus 484,674 in 2000 — and New Orleans no longer has the hobbled-town vibe that followed the 2005 storm. Its post-Katrina economy is stable, thanks to rapid job growth. Louisiana likes retirees: The first $6,000 a year withdrawn from a private retirement plan is free of state taxes, and all withdrawals are free for retired government workers and military personnel.

Beyond Mardi Gras and the clubs and restaurants, New Orleans has accessible outdoor play space and a range of educational options. The metro has 534 miles of coastline, plus fishing and boating on Lake Pontchartrain. Audubon Nature Institute, at the west end of Magazine Street, has a complex of museums including a zoo, an aquarium, an “Insectarium,” and a nature study center.  Schools include the public University of New Orleans (enrollment 11,276), Delgado Community College (19,000), Tulane University (11,464), and smaller private, technical and professional schools.

OK, back to what makes NOLA special: You can experience it at Jazz National Historical Park in the French Quarter (look past the grime to the music and food), the emergent Faubourg Marigny neighborhood and Casamento’s restaurant, where an unassuming decor masks the best oysters in the city (really).

In a 2007 CNN poll, Americans ranked New Orleans tops among 25 U.S. travel destinations for flea markets, antique shopping, cheap food, cocktail hour, live music, going out at night, “wild weekends” and “girlfriend getaways.”  Residents of the Big Easy were also ranked the most fun. But New Orleans was also ranked the dirtiest and most unsafe destination, and its residents were judged to be the least athletic. 

Fortunately, then, the metro area has a high concentration of physicians, cardiologists and hospital beds. Violent and property crime rates are both very high. More residents are walking, cycling and using mass transit — another hopeful sign in a city that often runs on positive emotions.

Ithaca, N.Y.

It may seem incongruous to call a company town “quirky.” But in Ithaca, the “company” is Cornell University and the student population of 21,000 roughly equals the number of permanent residents, resulting in an eccentric, hippie haven where it’s easy to feel forever young.

Enough Cornell students hail from New York City, 175 miles southwest, to make parts of Ithaca feel like the Upper West Side. Cornell’s sprawling campus marches up East Hill and dominates the skyline; Ithaca College (enrollment 6,949) perches on the South Hill; and West Hill is a quiet residential neighborhood. At the northern edge of town is Cayuga Lake, a glacial trough 38 miles long. Downtown Ithaca sits at the south end of the lake and, because of the water, is usually a tad warmer than the hills — small consolation in February, when the average high is 34 degrees.

The economy is relatively solid here. At 7.6 percent, unemployment is slightly lower than the U.S. average, but many jobs don’t pay well. Retirees have other advantages: You can withdraw $20,000 a year from a qualified private pension without paying New York State tax, and all withdrawals are free for retired soldiers and government workers.

The town’s arts and entertainment scene is small but power-packed. The historic State Theatre, a 1,200-seat movie palace downtown that opened in 1928, hosts dozens of musical, theater and community events yearly. Local musicians with New York City and Boston connections keep the stages at local bars hot. Cornell’s Johnson Museum of Art (free) has strong collections of Asian and contemporary art. There are also a lot of painters and sculptors working here, plus an Arts Partnership that coordinates studio tours and fairs.

The Ithaca Farmers Market, on the lake shore, is a packed Saturday morning social hour. Fresh produce is big among the region’s many wineries, organic farms and talented chefs.

For outdoorsy types, Ithaca is surrounded by state forests and nature preserves that draw hikers, mountain bikers and cross-country skiers. Waterfalls abound.

Ithaca scores well in health and safety, thanks to low crime rates, the highly ranked Cayuga Medical Center and admirable preventive care community programs. Locals enjoy a long life expectancy, in part because of low rates of obesity, high cholesterol and diabetes.

The bleak weather in this laid-back town can’t be too dispiriting: Ithaca boasts a very low score on our stress index, which measures the rates of suicide, divorce, poor mental health, unemployment and crime, among other things.

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.

Providence, R.I.

The salt air may not cure all but it gives people who are prone to whimsy — like retirees! — an excellent excuse to throw caution to the wind. In Providence, that may mean hoisting a mainsail and clipping out to sea, strolling a beach or dropping into any number of seafood restaurants.

This metro area of 1.6 million takes in the state of Rhode Island as well as Bristol County in southern Massachusetts. Providence (population 178,042) sits at the head of Narragansett Bay.

Rhode Island’s economy was hit hard by the recession and remains stalled. The state’s unemployment rate — 11 percent in February 2012 — is above the national average and job growth is stagnant. 

But many towns and neighborhoods are holding up fine. Downtown Providence has done a great job of saving and restoring its historic buildings. You can walk out of a loft carved out of an old warehouse to stroll amid the Victorian buildings and carousels of Roger Williams Park, or hit Brown University (enrollment 13,294) for an independent film or a play. The city has become famous for WaterFire, a celebration where 100 bonfires are set afloat on the three rivers that meander through downtown.

Providence’s cultural scene is small but energetic and includes the Rhode Island School of Design, where David Byrne and two alumni formed the Talking Heads, and Johnson and Wales University, a world-renowned culinary school. The Design School has a big museum of contemporary art, and nearby are several major venues for classical music and theater, led by the Providence Performing Arts Center.

There are large community colleges in Warwick and Fall River, the University of Rhode Island in Kingston (enrollment 13,200), and a branch of the University of Massachusetts in Dartmouth (enrollment 9,432). Roger Williams University (enrollment 4,680) is in the well-preserved waterfront town of Bristol. Newport has Salve Regina University (enrollment 2,584), with its lifelong learning program, and the International Yacht Restoration School.

Crime is low in the Providence area. The availability of doctors and hospitals is adequate, and Rhode Islanders' health is near national averages in most respects.

Still, a high proportion of locals also report that they don't get the emotional support they need. And given the economic problems many face, it's not surprising that they also report being dissatisfied with life. Chances are, if you gave the average local resident enough money to spend a weekend at the nearby beach, he’d buy a week’s worth of groceries instead. 

Santa Fe, N.M.

For anyone who says Santa Fe’s quirkiest days are behind it, we offer Zozobra. The 50-foot-high marionette of gloom, constructed anew annually and adorned with residents’ written details of their worries, goes up in flames at the yearly Fiesta de Santa Fe, signifying the literal and figurative incineration of all that weighs on the locals.

Then again, it is unclear precisely what concerns one would have in this paradise in the foothills of the southern Rocky Mountains. Santa Fe is home to innovative restaurants, offbeat boutiques, dozens of galleries (art and otherwise), spectacular scenery and dry, sunny weather.

Santa Fe (population 67,947) is 55 miles northeast of Albuquerque. Half of the metro area's population is Hispanic, some from families that have lived here 10 generations or more.

The city is an epicenter for painting and sculpture. There's also a local symphony, community orchestra, several chorales, the Santa Fe Opera, and annual festivals for chamber music, folk and bluegrass, alternative theater and more. Santa Fe is also a big foodie scene: Trattoria Nostrani has won numerous awards, and other restaurants, including El Farol, employ innovative chefs. You'll find them browsing the Tuesday and Saturday farmer's market for native chilies, mountain apricots, biscochitos (New Mexico's traditional cookie) and more.

On Sundays, walk the craft stalls in front of the city's old plaza, next to the oldest public building in the United States, the Palace of the Governors, built in the early 17th century. Or wander into the myriad shops, galleries, cafes and bars, or the 96,000-square-foot New Mexico History Museum. Gallery Row along Canyon Road was named one of America’s Great Streets by the American Planning Association.

In the Sangre De Cristo Mountains surrounding the city, you can walk or mountain bike for days. Need a hiking partner? Call the Trails of Santa Fe Stewardship Coalition. For skiing, hit Ski Santa Fe, just 16 miles from town, or drive 2 1/2 hours to the world-class steeps of Taos Ski Valley.

The local economy is mixed — low unemployment, but a growing population and high housing prices that have driven up the cost of living.

Santa Fe made AARP The Magazine’s list of the 10 healthiest places in the United States in 2008 due to residents' high life expectancy. But the metro area is near the bottom of the United States in the number of hospital beds per capita, so people often seek major treatments in Albuquerque. Santa Fe does have an ample supply of doctors, so basic medical attention is readily available, as are all manner of alternative healing and holistic medicine practices. Viva quirky!

Port Townsend, Wash.

Looking for a small town with a big sense of adventure, top-shelf boating right from town and majestic mountains a short skip away? If so, Port Townsend is calling. Even after 12.7 percent growth since 2000, fewer than 10,000 people live here year round, although the population swells during summer tourist season. And while Port Townsend is less than two hours north of Seattle by car, the town gets very little rainfall because the massive Olympic Mountains to the west wring the moisture out of Pacific storms.  (Full disclosure: While the “rain shadow” keeps Port Townsend relatively dry, it doesn’t block all the clouds. So overcast is the norm here.)

Downtown had the feel of a time warp: Well-preserved and restored Victorian buildings remain from the town’s original construction boom, around 1890. When the bust came a year or so later, the town meandered along, essentially frozen in time, for the next 90 years. Had any industry come along during those tough years, Port Townsend most likely would have been razed and rebuilt, like so many former boom towns in the United States. As it stands, today’s locals and tourists reap the aesthetic rewards of the century-long stall.

And the pace has clearly picked up: Among myriad annual festivals and side-stream events are a wooden boat festival, kinetic sculpture race, festival of American fiddle tunes, naturalist-led bird-watching walks and traveling exhibits, such as a recent showing of 1960s surf photography. A handful of bars in town keep the live music flowing, augmented by casual and social Thursday-night concerts on the dock at Pope Marine Park during summer. The Saturday farmers market draws chatty crowds from early April to Christmas.

Art lovers have a dozen galleries to browse, and you can sample them with like-minded locals on Saturday gallery walks. All of this has attracted retirees: Almost a quarter of the population is age 65 or older.

Port Townsend enjoys proximity to remarkable outdoor recreation: The Olympic Mountains rise on one side, with trails, streams, lakes and towering, snow-capped peaks. On the other side of town, Port Townsend Bay extends like a silken blanket, beckoning kayakers, sailors and power boaters. The parks in town include two with waterfront access and a third — Kah Tai Lagoon Nature Park — with a sizable lake.

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There are no higher education institutions in Port Townsend, but nearby towns such as Everett, Lynnwood and Shoreline have community colleges. Port Townsend lags the national average in doctors per capita, but residents tend to be healthy, with low rates of diabetes, obesity and hypertension. With so much to do and so little to worry about on this little peninsula, the health numbers aren’t surprising.

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