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10 Great Quirky Places to Retire (or nearby smaller towns)

10 funky and artsy cities that "free spirits" (i.e. not Trump voters) may love

If you're retiring and looking to move to an area with a different flavor, try these 10 cities.

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?

10 Quirky Places

  • • Ulster County, N.Y.
  • • Austin, Texas
  • • Boulder, Colo.
  • • Cape Cod, Mass.
  • • New Orleans
  • • Ithaca, N.Y.
  • • Portland, Ore.
  • • Providence, R.I.
  • • Santa Fe, N.M.
  • • Port Townsend, Wash.

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 villages are spread out along the Hudson River.

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.

Ulster County, N.Y.:

  • Nearest major airport: Stewart International Newburgh, 25 miles from New Paltz
  • Mean price for a single-family home: $242,100
  • Median household income: $57,584
  • Population: 182,493
  • Percent of residents age 65 and older: 14.8 percent
  • Cost of living: Above 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

Austin has a rich music and arts scene.

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, Texas:

  • Nearest major airport: Austin-Bergstrom International, 10 miles
  • Mean price for a single-family home: $200,000
  • Median household income: $50,520
  • Population: 790,390
  • Percent of residents age 65 and older: 7 percent
  • Cost of living: Below average

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, Colorado

Boulder's breathtaking scenery draws people from all walks of life.

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.

Boulder, Colorado:

  • Nearest major airport: Denver International, 44 miles
  • Mean price for a single-family home: $475,200
  • Median household income: $51,779
  • Population: 97,385
  • Percent of residents age 65 and older: 8.9 percent
  • Cost of living: Above average

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.

Cape Cod is a 65-mile peninsula that draws tourists from around the world.

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 (Barnstable County):

  • Nearest major airport: Boston Logan. Regional airports include Provincetown Municipal, 10 miles from the town center.
  • Mean price for a single-family home: $392,700
  • Median household income: $60,317
  • Population: 215,888
  • Percent of residents age 65 and older: 25 percent
  • Cost of living: Above average

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 recovered since Hurricane Katrina and is now a hotbed for retirees.

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.

New Orleans:

  • Nearest major airport: Louis Armstrong New Orleans International, 14 miles
  • Mean price for a single-family home: $184,100
  • Median household income: $37,468
  • Population: 343,829
  • Percent of residents age 65 and older: 10.9 percent
  • Cost of living: Average

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.

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

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.


  • Nearest major airport: Ithaca Tompkins Regional, 6 miles
  • Mean price for a single-family home: $171,400
  • Median household income: $30,919
  • Population: 30,014
  • Percent of residents age 65 and older: 5.9 percent
  • Cost of living: Above average

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.

Portland is known as one of the friendliest cities for bicyclists in the country.

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.


  • Nearest major airport: Portland International, 12 miles
  • Median price for a single-family home: $292,000
  • Median household income: $48,831
  • Population: 583,776
  • Percent of residents age 65 and older: 10.4 percent
  • Cost of living: Average

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.

Although Providence continues to recover from the recession, many of the towns and neighborhoods have not lost annual festivals and celebrations.

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.


  • Nearest major airport: T.F. Green, 10 miles
  • Mean price for a single-family home: $243,600
  • Median household income: $36,925
  • Population: 178,042
  • Percent of residents age 65 and older: 8.7 percent
  • Cost of living: Average

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.

Santa Fe holds firm to its southwestern roots, but is also home to innovative restaurants, offbeat boutiques and dozens of art galleries.

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:

  • Nearest major airport: Santa Fe Municipal, 14 miles
  • Mean price for a single-family home: $311,300
  • Median household income: $49,947
  • Population: 67,947
  • Percent of residents age 65 and older: 17.6 percent
  • Cost of living: Average

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, 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.

Port Townsend is less than two hours north of Seattle and is a hotbed for retirees.

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.)

Port Townsend:

  • Nearest major airport: Seattle-Tacoma International, 99 miles
  • Mean price for a single-family home: $305,600
  • Median household income: $43,597
  • Population: 9,113
  • Percent of residents age 65 and older: 24.5 percent
  • Cost of living: Below average

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.

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.

by John Briley, AARP 

To view this article in its entirety, including photographs of each location, Click Here

The Real Reasons People Retire

It’s not just about money. Health, family, and lifestyle choices are also key.

Key takeaways

While financial and work-related factors are the primary reasons people continue to work, nonfinancial factors like family, health, and lifestyle ultimately cause people to pull the trigger to retire.

Well-being in retirement is not just about money, or even intellectual stimulation. It's largely about the freedom to do what you want, when you want.

As you enter a stage of pre-retirement, consider working with your financial advisor to help shape strategies for Social Security, health care, and cash flow in retirement.

When will you be ready to retire? Particularly if retirement is still far away, you're probably thinking in terms of dollars—how many you will have and how long they will last. But new research finds that for many people, the decision to retire is not just about money. It's about life, and the freedom to enjoy it.

That's the conclusion of an extensive survey of over 10,000 pre-retirees and recent retirees. The online survey was conducted by Fidelity Investments in collaboration with the Stanford Center on Longevity and Greenwald & Associates and only included respondents who believed they had some control over if and when they would stop working full-time.

While financial and work-related factors are the primary reasons people continue to work, with eligibility for Medicare and Social Security as key factors, the survey also finds that it's often non-financial factors like family, health, and lifestyle that ultimately cause people to pull the trigger to retire.

Among retirees, 72% chose leisure as a very or somewhat strong reason to retire, 64% pointed to stress at work, 63% cited a desire to spend more time with grandchildren, 55% chose pursuit of hobbies, and 54% chose travel as their primary reason to retire.

"We've seen a shift in values as people near retirement," says Fidelity's Eliza Badeau. "Many people seem to desire freedom over money. It's less about the money and more about spending time where it matters most to them," she adds. "Most people say they look forward to the freedom that retirement brings such as spending time with their family or doing hobbies they enjoy—ultimately trading in that job stress for leisurely interests."

3 phases of "pretirement"

The research found that there are 3 distinct phases of "pretirement" that many pre-retirees go through and assume they will have some control over the actual timing of their retirement. The phases are not age-based, but rooted in life stages.

(1) In early pretirement (10 or more years out), the survey finds that most people still have significant debt, are not sure they can make their money last, and are likely to still have children and/or aging parents to support. People in this stage are generally in good health, happy with their job, and looking forward to new professional challenges.

(2) In mid-pretirement (2 to 9 years out), people are starting to reduce debt, are less responsible financially for their children, and are feeling as though they might be able to make their money last throughout retirement. Meanwhile, their professional drive may plateau. They may still like their job, but find themselves less interested in new opportunities—and more interested in free time for leisure and family.

(3) By late pretirement (less than 2 years out), people's priorities have shifted. They feel more confident that they can make their money last through retirement. They often feel more job-related stress, and no longer look for new job-related opportunities—they've effectively put their resume to bed. Many feel that their physical stamina declines along with their mental sharpness. They really want more time for leisure and family.

The emotions connected to retirement shift along the way too. In early pretirement, some people are stressed about their ability to live comfortably in retirement. But by the time they reach late pretirement, most feel more financially secure and excited about a new chapter. Among recent retirees, those who left their primary career within 2 years of participating in this survey, almost 80% say it's easier than they thought to live comfortably in retirement and 85% say it's the most rewarding time of their lives. Only 10% say they are worried about being bored.

What does this mean for you?

Here are a few tips to make sure you are ready—both financially and emotionally.

Rev up your retirement savings. In our survey, health care costs, general economic conditions, and lack of confidence that pre-retirees could make their money last throughout their retirement were the 3 most important financial factors in the decision to keep working. If these factors resonate with you, consider working with an advisor on the following steps to help boost your retirement readiness:

1. Try to turn any extra money—bonuses, raises, or reduced expenses—into savings.

2. Max out on tax-advantaged workplace retirement plans like 401(k) or 403(b) plans, and contribute at least enough to meet any company match.

3. If you can save more, contribute to an IRAs as well.

4. If you are age 50 or older, take advantage of additional catch-up contributions for both 401(k)s, 403(b)s, and IRAs.

5. Reduce and ultimately eliminate any high-interest rate debt.

6. Invest appropriately for your age, risk tolerance, and goals, either on your own, or consider using a managed account.

Make sure you plan for health care costs and your health too. Remember that Medicare does not kick in until age 65 and, even then, it does not cover all health care costs in retirement. Fidelity estimates that a 65-year-old couple should expect to spend $285,000 over the course of retirement on health care costs on average.2 So you will want to factor in those costs as well. If you have a health savings account at work, it can help you save for health care costs in retirement. Also, consider purchasing long-term-care insurance.

Perhaps most important, try to stay healthy and attempt to manage stress. Among pre-retirees in our survey, 55% said stress was a "strong" or "somewhat strong" factor in their decision to leave the workforce. Among retirees, it was 64%. Know the causes of stress in your life (poor health, demanding job, new technology, terrible commute, etc.) and develop coping strategies. When the stress of work clearly begins to negatively affect your health (despite efforts to find ways to manage the current challenges), it may be time to accelerate your transition to retirement—and preserve your peace of mind.

Finally, remember that well-being in retirement is not just about money, or even intellectual stimulation. As pre-retirees and retirees told us, it's also about the freedom to do what you want, when you want.

Think about what is important to you, and how you want to spend your time. Maybe it's traveling, or reading, or fishing, or jumping out of a plane (with a parachute of course), as one 90-year-old recently did. Maybe it's starting a new business, consulting, mentoring others, or volunteering. Or maybe it's spending more time with your spouse or your kids and grandkids.

Why people keep working: 67% respond money, 29% job, 21% lifestyle, 19% Health, and 11% Family.

Now may be the time to take your sabbatical

While working full-time, you probably did not have a lot of time for reflection to think about "what's next?" Assuming you've achieved financial freedom as a new retiree, you'll likely deal with a lot of emotion as you begin to see yourself in a new light and ask: What do I want to do now? What is my passion? How do I want to spend my time?

One way to ease the transition to retirement is to think about this new phase of your life as a sabbatical, advises Chris Farrell, author of Purpose and a Paycheck. "Older adults want a break from the demands of a job. They retire. Yet they often return to the workforce within a year or 2. In fact, about 40% of Americans age 65 and older who are currently employed were retired at some time in the past," says Farrell.

He adds: "In other words, consider taking a sabbatical to recharge your batteries and think through what you want to do next."

Part-time employment and flexible jobs are popular. So is nonprofit work, especially for those with careers in for-profit companies and professional organizations. These encore careers typically come with a smaller paycheck, but the mission or cause of the organization is meaningful. Entrepreneurship and self-employment are attractive to many people at this stage of life.

"A key to success is your willingness to experiment, to see what jobs might intrigue you and steering clear of pursuits that leave you cold," says Farrell. "You'll want to focus on understanding the skills and knowledge you've developed over the years. Skills are very different from jobs and job titles. Adopt an entrepreneurial mindset when it comes to exploring what comes next, even if you've never considered starting your own business before."

Tip: Experienced workers usually find new jobs and opportunities through their network, says Farrell. During your sabbatical, talk to the people in your network. Ask them to identify your top skills and interests. Make a list. What do they see you doing next? Ask them to tap into their network to set up informational interviews for you during your sabbatical. Remember, most jobs come from a referral rather than a resume.

Plan ahead

You may be ready to stop working, or you may just be thinking about doing so financially and emotionally. Whichever is the case, consider working with an advisor to help shape your strategy for Social Security, health care, and cash flow in retirement. It can help you get where you want to go. For many people, the decision to retire is not just about money. It's about life, and the freedom to enjoy it.

Retirement factors: A checklist for "pretirees"

Financial (consider discussing with your finacial advisor)

Are you financially ready to retire?

How can you take advantage of ways to save more?

What steps are needed to create a retirement income and portfolio strategy to make the most of your retirement assets?

Do you have an understanding of how health care and Social Security will affect your expenses and income strategy in retirement?


Imagine that you will have unlimited time and resources upon retirement. What unfulfilled passion or dream would you wholeheartedly pursue?

Recall all the things you loved doing in your teens or twenties (e.g., hiking, dancing, traveling, playing guitar) and make a plan to bring the joy of those experiences back into your life—in a new way.

Where would you like to live? Make a Top 3 list.

What would you like to do? Try filling out a 1-month retirement calendar to make your priorities tangible.

Make a "bucket list" of special things you want to do and places you want to visit during your first 5 years of retirement.

Have you discussed your dreams with your spouse or partner? If not, make a date to discuss.

Family and friends

Do you want to spend more time with your spouse? In our study, nearly 60% of husbands want to spend more time with their wives in retirement, but only 43% of wives want to spend more time with their husbands.

Examine the role you’ll play with your extended family. How might being a grandparent be different (perhaps even better) than raising your own kids? How much time do you want to spend with them?

What about friends? Are there friends you want to reconnect with? Are there coworkers you may want to keep in touch with? How will you grow and maintain friendships? How will you meet new people?


Do you understand your options for enrolling in Medicare?

Do you have a retiree medical plan? If so, do you understand your benefits?

Do you need supplemental medical insurance?

Are you under stress at work? How can you reduce it?

The best way to reduce health costs over time is to stay healthy. Go for a walk and make some healthy resolutions, like improving your diet.


Think about how much longer you really want to work.

Ask coworkers and your HR department about "phased retirement" or part-time or flexible work options. You may be able to reduce your work schedule while maintaining health benefits.

Participate in "mentoring" programs that allow you to share your skills and wisdom with younger work colleagues.

Begin to explore encore careers and volunteer opportunities you can pursue in retirement that leverage your skill set, hidden talents, and interests.

Fidelity Viewpoints – 05/20/2019 

8 Simple and Relevant First Steps to Prepare for Your Retirement

In this article, I am providing a sort of "starter kit" for those of you who are getting closer to retirement - and want to consider the basic variables for a mostly stress-free transition when you do retire.

Here are eight initial first steps to get you thinking about a "low drama" retirement:

1. Figure out how much you need to spend.

Many financial advisers use a rule of thumb for needed retirement income of 60 to 66 percent of current pretax income. However, this estimate is just a rule of thumb for an average case.

To estimate your retirement expenses yourself, begin with a baseline, and then make adjustments.

For your beginning baseline, start with your current monthly income. This will give you an idea of how much you currently spend each month. Then deduct expenses that you currently have that will disappear after retirement.[1]

  • For example, suppose your current monthly income is $5,000 after taxes. Assume that your monthly expenses equal your monthly income, so begin with this number.
  • Deduct your savings. After retirement, you won’t be saving any more. Suppose you save $500 each month. Deduct that from your total ($5,000 − $500 = $4,500).
  • Deduct how much you’ll save in living expenses if your home is paid off by the time you retire. For example, if you're paying $1,000 per month towards your home and it is paid off, you no longer have to pay that amount in retirement ($4,500 − $1,000 = $3,500).

2. Calculate what annual income you need after retirement.

Determine how much income you will receive from your current retirement savings, including Social Security, your pension and any retirement accounts you already have. Compare that monthly income with your estimated monthly expenses. Multiply that number by 12 to get your yearly income gap.[3]

  • Using the above example, you estimated that you will spend $4,000 each month in retirement.
  • Suppose you know you will receive $2,100 from Social Security and $3,250 per month from your pension. Your monthly income will be $5,350.
  • Your income gap is $5,350 − $4000 = $1,350 x 12 = $15,600

3. Calculate how much you will need to save or invest before retirement

Assume you will want to withdraw 4 percent from your retirement savings per year. Multiply your annual income gap by 25 to estimate 25 years of living past retirement. This will tell you how much more you need to save between now and retirement in order to have enough.[4]

  • In the above example, you annual income gap is $15,600.
  • Multiply this by 25 ($15,600 x 25 years = $390,000.
  • You need to save an additional $390,000 using retirement accounts such as a 403(b), 401(k) or IRAs.
  • These numbers are rough estimates and presume no substantial draw downs of principal after retirement.
  • You may have to adjust your calculations to include more years of retirement if your spouse is much younger than you are.
  • How you save or invest that money is a discussion you should have with me (Rocky) at your request.

4. Consider changes in your retirement lifestyle.

If you are going to travel regularly, then some expenses might increase. However, you might also decide you need to spend less on commuting, clothing and groceries.

Suppose you can reduce your monthly transportation, grocery and clothing budget by $300 per month. But, you plan to take one large trip each year for $5,000, so you plan to save $450 per month for this trip. The net change means adding $150 per month to your budget ($3,500 + $150 = $3,650)

5. Decide when to apply for Social Security benefits.

The age at which you begin to collect Social Security benefits affects the percentage of benefits you will actually receive. Choosing the optimum age at which you should apply for benefits depends on many factors. Consider your life expectancy and financial picture to decide how long to wait.

  • Waiting until full retirement age allows you to collect 100 percent of your Social Security benefits. If you were born before 1938, full retirement age is 65 years old. For those born in 1938 and after, full retirement age can be up to 67 years of age.
  • To determine your full retirement age, refer to the Social Security Administration’s retirement chart at
  • If you can wait until age 70 to collect Social Security, you can collect an even higher monthly check (persons born after 1943 earn an increased benefit of 8 percent per year of deferral).
  • You can begin collecting Social Security as young as age 62. However, you will receive a permanently reduced amount. If your full retirement age is 67 and you begin collecting at age 62, your benefit amount will be reduced by 30 percent.
  • If you have other financial resources, it makes sense to delay collecting Social Security benefits until you are of full retirement age.
  • If you will have high expenses in your retirement, such as if you devote much of your retirement income to an entrepreneurial goal or if you are in poor health, it may make more sense to begin collecting Social Security benefits at a younger age. This make sure that you have a steady enough income through this time to support your living expenses.

7. If you plan to move after retirement, choose the right time.

Downsizing is a part of many people’s retirement plan. However, leaving the family home may also require leaving behind a community and connections that are important to you. Picking the right time to leave your family home is a personal decision. For some, the change happens when both partners in a marriage are still alive and want to spend time together in a different place. For others, the death of a spouse prompts the decision to move. When you decide that the time has come to look for new housing in retirement, consider not only your budget, but also your lifestyle, the proximity to your family and the status of your health.

8. Consider what your health will be like after retirement.

If you are in good health, you can choose to live independently. However, you must accept that changes in your health are an unavoidable part of aging. Your health status can change gradually, or you may experience a sudden decline in health. If you have enough money, you can stay in your home and arrange for professional caretakers to help you. If not, you may have to arrange to either live with a family member or move to a facility where you will be cared for.


Note: When you are ready to discuss your retirement plans or want clarification regarding any of these retirement planning points, please contact me as desired. 

Rocky Boschert

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