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Best Places to Retire

10 Great Small Cities for Retirement

Looking for a place where there's lots to do, but you won't get lost in the crowd? Check out our top picks

People parade through Winchester, VA on July 4.

The July 4th parade in Winchester, Virginia, is one of the city's many signature celebrations. — Michael Beslant

Winchester, Virginia

For aspiring retirees who want space, fresh air and quietude but want it within arm's reach of a major city, Winchester, Va., is calling. Nestled in rolling horse country 65 miles west of Washington, D.C., Winchester is growing but still has a relaxed, unpretentious vibe. The metro area crosses north into West Virginia and harbors about 125,000 residents altogether; 26,000 live in Winchester proper.

See also: The best places to live the simple life

For budget-conscious retirees (and these days, who isn't?) Winchester offers a below-average cost-of-living and access to job training — for example, at Lord Fairfax Community College (enrollment 5,100) in Middletown, about 10 miles south of Winchester. Also, Shenandoah University (enrollment 2,900), in Winchester, welcomes older students at a Center for Lifelong Learning.

Retirees here split time between outdoor activities — golf courses abound, and George Washington National Forest and Shenandoah National Park are mere miles from town — and a historic downtown that boasts a variety of shops, restaurants and galleries. There is also an active equestrian scene, with a club for horsey folks that organizes shows, rides and exhibitions. The Great Allegheny Passage, a bicycle path that runs uninterrupted from Washington, D.C., to Pittsburgh, is just across the Potomac River a few miles north of the city.
Winchester has a nice little arts scene, too. The local symphony performs at the historic George Washington Hotel downtown, among other places. There's professional theater at the Wayside in Middletown, and community productions at the Winchester Little Theatre. Shenandoah University has a large conservatory, with student recitals and other performances.

On the West Virginia side of the area, where a mellower pace prevails, (Ridgeway, W.Va., is 10 miles north of town), the Hampshire County Arts Council links an active community of working artists who keep a lower profile. The substantial cultural assets of D.C.'s northern suburbs are within easy reach, especially if you avoid rush hour.

The area also shows off its history. Attractions include the surveying office George Washington used when he lived here in the 1740s; a Civil War center, numerous battlefields and a war-themed weekend held every fall; and the Patsy Cline Historic House, where the country music star lived with her mother and siblings.

For all its laid-back country charm, Winchester loves to throw grand parties. One high point on the social calendar is the Shenandoah Apple Blossom Festival in late April, an extravaganza that lasts more than a week and includes parades, concerts, a circus and the coronation of Queen Shenandoah.

Riding a bike in Corvallis, OR. 10 Great Small Cities for Retirement.

Hiking, walking and cycling are among the popular outdoor activities among retirees in Corvallis, Oregon. — Zuma Press, Inc./Alamy

Corvallis, Oregon

Spend a little time in Oregon's Willamette Valley and you'll understand why so many settlers planted themselves here after surviving the Oregon Trail. Corvallis (translation: Heart of the Valley) sits in the middle of that broad valley between the Oregon Coast and Cascade mountain ranges in a pretty — and extremely fertile — swath of land.

See also: America's healthiest hometowns

The heart of Corvallis is Oregon State University (OSU, enrollment 19,000), which is a major research center for oceanography, aerospace, veterinary medicine and renewable energy. The 500-acre campus hosts art exhibits, plays, concerts and films, and is surrounded by the inviting trappings of many college towns — cafes, bars, bookstores and shops. But don't think it's all youngsters here: Aside from the large professional class, tourism brings solid waves of seniors to Corvallis every summer.

Downtown Corvallis, while not postcard perfect, does have a handful of nice boutiques, a decent selection of restaurants, including one that doubles as an organic farm. The regional wines are respectable, and the town has a popular and colorful Saturday farmer's market. Of the numerous festivals in and around Corvallis, the most popular is Da Vinci Days, a three-day celebration of arts, science and technology held every July.

Corvallis is 40 miles northwest of Eugene and 70 miles south of Portland (one-fifth of Corvallis' working population commutes to the Portland area). The metro area has few residents who consider themselves religious (only Medford, Ore., is lower) and in 2006 ranked second highest for percentage of scientists in the workforce (behind Boulder, Colo.).

In 2011, Corvallis had the highest percentage of residents in the U.S. who bike to work (9.3 percent) and ranked second in the percentage who walk to their jobs. Ninety-seven percent of the city's main roads have bike lanes, and almost 16 miles of bike trails run through the city. The Willamette and Marys rivers also run through town.

On the downside, many jobs in Corvallis pay poorly. Unemployment is below the national average but the cost of living is much higher than the median household income. The culprit is housing prices, which are near the top one-10th of all U.S. metro areas. On the plus side, most pension income in Oregon is free of state income taxes.

For the outdoorsy, the crest of the Cascade mountain range is about 75 miles east of Corvallis, with great skiing and hiking. The coast is 40 miles west, with beaches, the Oregon Dunes National Recreation Area and Siuslaw National Forest. OSU's research forests are crisscrossed with good mountain biking trails.

The Pioneer Valley of Massachusetts is a popular place to retire- a golfer walks through a course in Amherst, MA

The Pioneer Valley around Springfield, Massachusetts, has broad appeal for retirees. — Jessica Rinaldi/Reuters

Springfield, Massachusetts

Seeking a small city that will make you feel young without making you act like a teenager? Springfield's burgeoning nightclub scene helps give the city a youthful energy but its dozens of restaurants and pubs, coupled with cultural offerings, provide ample adult environs for retirees to relax.

See also: 10 places for outdoors lovers

For the culturally inclined, museums, galleries and shows abound, including the Quadrangle, a cluster of five world-class museums on Chestnut Street, surrounding the Dr. Seuss National Memorial Sculpture Garden. For kids of all ages, the Eric Carle Museum of Picture Book Art celebrates the children's author.

Springfield is the heart of Pioneer Valley, Mass., which spans three counties — Franklin, Hampshire and Hampden.

That village feel is evident on the outskirts of some of the smaller cities, including Westfield (population 40,000), Holyoke (40,000), Amherst (34,000) and Northampton (28,000).

Springfield Symphony Hall, an ornate space built in 1911-1913, hosts classical music and traveling Broadway shows while its sister venue, CityStage features a wider range of performances.

For retirees seeking continuing education, opportunities abound. The University of Massachusetts-Amherst (enrollment 24,300) is the flagship of the state system, but there's more beyond that. The colleges of Hampshire, Amherst, Mount Holyoke, Smith and U. Mass-Amherst collaborate to offer courses to older learners through Five College Learning in Retirement. Springfield College offers a program of its own called Learning in Later Life.

There are also countless historical sites and home museums here, including the home of Emily Dickinson in Amherst and historic Deerfield, a pioneer village that has been preserved intact and is open for tourists.

Outdoor recreation opportunities are also abundant. Boating and fishing are popular on the Connecticut River and other nearby waterways. Mount Holyoke Range State Park offer hiking, horseback riding and cross-country skiing. For alpine skiing, the valley is an easy day trip to numerous small ski resorts. Golfers have numerous quality courses to choose form as well.

Drawbacks? The cost of living is in the top one-fifth of United States metro areas, but the median household income is only a little above the national average. Blame home prices, which took off during the housing bubble; foreclosures are a big problem in some parts of the metro.

Napa Valley is a popular place to retire for wine lovers and foodies

Napa Valley is a popular place to retire for wine lovers and foodies. — David Paul Morris/Getty Images

Napa, California

In terms of its main attraction — wine — Napa, Calif., needs no introduction. But there is far more to this scenic town than matters of the grape. Historic buildings, hiking, biking, hot springs and spas are on tap, and the town of Napa is only an hour's drive from the coast (though it's a two-hour drive — when traffic is light — to the Golden Gate Bridge).

See also: 5 happiest cities in America

Given the Napa Valley's reputation for high-end wine, food and vacationing, it won't shock you that it's a pricey place to live. But, let's admit it: Those prices help keep things classy! Development is limited by strict regional zoning laws, which have saved the valley from mega-sprawl and preserved a small-town feel. The recession has impacted Napa, primarily by moving real estate prices from stratospheric to merely outrageous.

Napa is one of five towns in the valley and all have that California vacation town feel that makes for a great retirement locale. The other towns are Calistoga, Oakville/Rutherford, St. Helena and Yountville. Most of the valley is flat agricultural land, with side canyons cutting into tall, steep hills on either side. The hills protect the valley from wind and give it a stable Mediterranean climate that produces world-class wine.

There are hundreds of wineries in the region, including 24 tasting rooms in downtown Napa alone. But the town also includes dozens of other businesses, many lining an outdoor pedestrian town center. Many of course are high end, like the Mustard Seed  (voted best clothing boutique in Napa Valley 16 years running) and Quent Cordair Fine Art, but there reasonably priced markets, outlet shops and department stores.

Many 19th-century buildings on Napa's main street have been saved and restored, including the Pfeiffer Building (1875), which is now a multi-winery tasting room, the Historic Napa Mill and the Napa Valley Opera House, which maintains a full calendar of musical and theatrical shows.

The town of Calistoga (population 5,000) and its famous hot springs and mud baths are 25 miles north of Napa. The vibe here is less precious than in Napa, and the town's small main street is convenient to decent hiking in the surrounding hills.

For retirees seeking expanded horizons, Napa Valley College (enrollment 7,700) as well as Pacific Union College (1,500 students) offer classes and programs.  

Locals tend to be healthy, aided by the Mediterranean climate — pleasant, sometimes-cool winters and warm sometimes-hot summers — conducive to outdoor activity. Most of the 23 inches of annual rain fall November through March. Besides biking and hiking, outdoor recreation includes kayaking and sailing on San Pablo Bay (the north end of the San Francisco Bay), tennis, golf and the usual slate of beach sports along the coast, an hour west.

Lewiston, Maine is home to the Great Falls Balloon Festival each summer

Lewiston, Maine, is home to the Great Falls Balloon Festival each summer. — Robert Bukaty/AP

Lewiston, Maine

Artists, nature lovers and owners of thick winter coats unite! Lewiston, a post industrial town on the Androscoggin River, has quietly emerged as peaceful artist community — and retirement outpost — 30 miles north of Portland.

See also: America's friendliest cities

Lewiston is rarely mentioned these days without its companion city, Auburn, which occupies the opposing bank of the Androscoggin. Together know as L-A, the area is within an hour's drive of the coast, the mountains, Portland and Augusta, and is 120 miles northeast of Boston.

The attraction for the older set is in the numbers: a high percentage of locals are age 65 and older.
One major lure for retirees on a budget is affordable housing and, for the artistically inclined, spacious, affordable studio space, much of it in high-ceilinged, 19th-century buildings.

Such space is on prominent display in the Bates Mill Complex, a collection of former mill buildings that has been redeveloped into offices, retail shops and housing. One tenant, Museum L-A, highlights the textile, shoe and brick industries that once thrived here. The past is also celebrated at the Franco-American Heritage Center — roughly half of the metro's population reports French or French-Canadian ancestry.

Bates College (enrollment: 1,700) has a large art museum and the Olin Arts Center, which includes a 300-seat concert hall; both are adjacent to a downtown arts district that has several theater companies. The large public library downtown holds concerts and film festivals in its Marsden Hartley Cultural Center. The L-A area also hosts numerous annual festivals, including the Liberty Festival, Moxie Festival, FrancoFun and Great Falls Balloon Festival.

If you're in that "semiretired" mode and hoping to work, incomes here are fairly low: median household income and cost of living are near the lowest one-third of U.S. metro areas, and that has restrained some expansion of the area.

But encouraging signs abound, including the recent addition of a $13 million Marriott Residence Inn in downtown Lewiston. Also, the area has a very low crime rate, with violent crime almost unheard of (which makes one wonder where author Stephen King, a hometown hero, drew his inspiration).

For the active set, the Androscoggin River connects to hundreds of lakes and streams where anglers can cast for Atlantic salmon, striped bass and more. There's good cross-country skiing right in town, and many downhill ski areas are a short drive away. A local group maintains bike paths along the river and is expanding a network of footpaths across the region.


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