Which small American town should you move to? [QUIZ]

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Different Strokes for Different Folks

Women, Cullinane says, may prioritize ample storage, low maintenance, security options, built-in organizers in bathrooms and closets or two master bedrooms to accommodate a non-romantic roommate. LGBT retirees may look for a community among other LGBT individuals where they don’t have to worry about discrimination or being separated from their spouse or partner.

They are just two groups who may seek out what Cullinane calls “niche” communities where they can live with or near others who share their background or interests. She ticks off a long list of examples, including communities tailored to Indian Americans, Asian Americans, LGBT individuals and couples, women who want to live with women, artists, sea-faring sorts and RV-abiding wanderers.

For some, that wanderlust is increasingly taking them abroad. She says that while statistics on the number of American retirees living outside the country are difficult to come by, some 600,000 Social Security checks were sent overseas in June 2014 – more than double the number sent out in 2002.

“Stretching their money, a spirit of adventure and longing for change might spur people to make the move,” Cullinane says.

Despite this growing number of retired expats, she notes that it's domestic cities that are most popular among retirees and, yes, some of them are in Florida and Arizona. Specifically, she says Naples, Fla., Prescott, Ariz., Austin, Texas, Charleston, S.C., and Asheville, N.C., are in demand among the recently retired. In fact, according to the U.S. Census, the fastest growing metro area in the U.S. from June 2013 to June 2014 was an “active-adult” community in Florida called The Villages.

But what if one’s hometown already has all the qualities a retiree could want? Cullinane says for some, staying put is the best option.

“Social connections have formed, doctors and dentists are in place, children may live close by,” she says.

That’s the case for Sharon Gentzler, who chose to stay in Casper, Wyo., after she retired in 2011. She’s lived in the small city since 1964, and has developed strong personal and professional relationships in the area. Though she’s considered living elsewhere, at the time of her retirement, she didn’t want to leave behind an elderly relative who had been like a mother to her.

“I wanted to and felt a moral obligation to be here for her,” Gentzler says.

As a social butterfly with limited retirement savings, she also appreciated the company of her friends and the ability to work part-time for former employers. When that beloved relative passed away a few years later, Gentzler inherited her home, making an even more compelling case for sticking around.

“For right now, I’m going to stay here,” she says, adding that Casper has plenty to offer her, including an affordable cost of living, ease of getting around and access to everything she needs, including quality health care. “If I want something more than what’s here, there are places I can go to get it.”

Cullinane says familiarity is a strong draw for retirees. Still, she encourages retirees to consider whether they are staying because they want to or because they don’t want to deal with the stress of relocating.

“There is something behavioral economists call the status quo bias,” Cullinane says. “It’s easier to do nothing than something, so although a majority of people say they are going to age in place, they may be doing it because it’s easier to stay than to make the effort to investigate places and relocate.”

Ultimately, every individual knows their own needs best. But Gentzler says the best advice she can give is to put money away so that when the time comes, retirees have more options to consider.

It’s easier to do nothing than something, so although a majority of people say they are going to age in place, they may be doing it because it’s easier to stay than to make the effort to investigate places and relocate.


Erin Rook is a writer and editor based in Bend, OR, who writes about livability, the environment, and LGBT and other social issues.

The 20 Best Small Towns in America of 2012

There are lists of the best places to get a job, retire, ski, golf and fall in love, best places lists for almost everything. We think any best place worth traveling to should have one quality above others: culture.

To help create our list, we asked the geographic information systems company Esri to search its data bases for high concentrations of museums, historic sites, botanic gardens, resident orchestras, art galleries and other cultural assets common to big cities. But we focused on towns with populations less than 25,000, so travelers could experience what might be called enlightened good times in an unhurried, charming setting. We also tried to select towns ranging across the lower 48.

There is, we think, something encouraging about finding culture in small-town America. Fabled overseas locales, world-class metropolises—you expect to be inspired when you go there. But to have your horizon shifted in a town of 6,000 by an unheralded gem of a painting or a song belted out from a band shell on a starry summer night, that’s special. It reinforces the truth that big cities and grand institutions per se don’t produce creative works, individuals do. And being reminded of that is fun.

50 of America’s Most Charming Small Towns

50. Fairhope, Alabama

This tiny Alabama town was founded in 1894 and is known for its annual shellfish phenomenon. Each year, crabs, flounder and shrimp flood the shallow bay in what’s referred to as the ‘jubilee’. In addition to the natural phenomenon, there’s a local brewery, tons of farmers markets, Museum of History and nearby Village Point Park Reserve.

49. Montpelier, Vermont

Montpelier is one of America’s most charming small towns. This fun capital town is famous for its Hubbard Park and the Vermont State House. With a history dating back to Native American settlers nearly 6,000 years ago, there’s plenty to be explored in this quaint, yet interesting town.

48. Mancos, Colorado

Tucked away in the valley of the LaPlata Mountains, you’ll find Mancos, Colorado. Its quirky art community, old West charm, tightknit community and scenic mountainscapes are what charms locals and tourists alike. Stroll the quaint historic streets, grab some goodies at a local farmers market or explore the wilderness by yurt camping. Either way, you’ll fall hard and fast for Mancos.

47. New Castle, Delaware

New Castle spins a tale of Delaware’s history with its peaceful cobblestone streets and old colonial town. Hugging the Delaware River, it’s surrounded by beautiful scenery and just a hop away from famous New Castle Battery Park. Additionally, history buffs will love their First State National Historic Park and Court House Museum.

46. Hilo, Hawaii

Hilo is surrounded by pristine tropical landscapes, home to a plethora of local markets and a vibrant Hawaiian culture. This Pacific pearl is mostly famous for its annual Merrie Monarch Festival dedicated to King David Kalakaua. Every year, the city is brought to life in a week-long celebration of Hawaiian tradition such as hula, crafts and the native language.

45. Wallace, Idaho

Home to a plethora of historic buildings, museums and local shops, it’s not hard to see why Wallace is so charming. For over a hundred years, Wallace has been the world’s largest silver producer, and it’s got a lot to show for it. For example, it’s the richest mining town still in existence and is listed on the National Register of Historic Places.

44. Lindsborg, Kansas

Lindsborg is famous for its rich Swedish history and is often referred to as ‘Little Sweden’. This quaint town of only 3,300 people perfectly embodies their Swedish heritage with local Scandinavian art, tons of traditional food and their founding festivals such as their famous Svensk Hyllningsfest.

43. Harpers Ferry, West Virginia

In the lower Shenandoah valley where Virginia, Maryland and West Virginia meet, you’ll find Harpers Ferry. This tiny town of only 300 is home to some pretty impressive historical sites such as John Brown’s Fort and several 19th-century buildings. In addition to the landmarks, it’s situated right on the Appalachian Trail.

42. Charlottesville, Virginia

Take a visit to Thomas Jefferson’s Monticello, James Monroe’s Highland or pop in the famous Paramount Theatre. But whatever you do, don’t leave without grabbing a bite at Miche Tavern, the circa 1784 eatery that uses only 18th-century recipes.

41. Cape May, New Jersey

Cape May, New Jersey an East Cost Victorian gem. With nearly 600 perfectly preserved Victorian buildings, the whole town is a historical area. In addition to stunning Victorian architecture, you’ll find excellent dining options, seaside activities and jazz festivals.

40. Homer, Alaska

This string of a city is nestled on the picturesque Kachemak Bay on the Kenai Peninsula. Take a stroll down the harbour and then spend an afternoon wandering the strip of shops, art galleries and local restaurants. Afterwards, hop over to the nearby wilderness park for some trails and kayaking.

39. Truckee, California

Truckee, California has long been a jewel of the West for adventurers. Only 30 minutes from Lake Tahoe, the surrounding area is just as interesting as the local town. In addition to an active art and music community, there’s a great dining scene making it one of the most charming small towns.

38. Ithaca, New York

Head to the heart of the Finger Lakes area in Ithaca, New York. This pint-sized town is the perfect place to spend a few days taking in the area and its charm. Take an artisan bread class, go ice skating in an outdoor pond and then catch some local talent at an old pub.

37. Newberry, South Carolina

Small town hospitality, natural beauty and colourful history come together to make Newberry one of the nation’s cutest small towns. Take a stroll through their tranquil Japanese gardens, wander historic downtown and then grab some local pieces at the Newberry Arts Centre.

36. Leiper’s Fork, Tennessee

This quaint country town is a mecca for antiques, history and quirky shops. The ‘kick-off your boots and stay-awhile’ mentality of the locals mixed with the surrounding beauty make it an easy favourite. Wet your whistle at one of the many cosy bars, chow down on a hearty meal at one of the local staples and then head to the Lawnchair Theatre.

35. Tarpon Springs, Florida

Allow yourself to be transported a tiny Greek village in Tarpon Springs. Thanks to the cities influx of Greek sponge divers in the early 1900s, you’ll find a unique Mediterranean influence throughout. Take a sunset walk down the beach or enjoy some delicious Greek fare in this sleepy coastal town.

Image: Tarpon Springs Sponge Docks / Facebook

34. Manitou Springs, Colorado

Rich in mineral springs, boutiques, mountainscapes and local arts, Manitou Springs is one of the nation’s most charming small towns. In the shadow of towering Pikes Peak, this Colorado gem is a village gateway to the natural world in addition to being charming and welcoming.

image: I Love Manitou Springs / Facebook

33. Ponchatoula, Louisiana

The teeny town of Ponchatoula is known for its Southern hospitality, historic old town and annual strawberry festival. In Ponchatoula, they take care of guests and each other. Take a walk around the local swamps, chow down on a hearty meal or make friends with locals at one of the old bars. Either way, you’ll feel right at home in this cosy Louisiana heartland.

32. Cannon Beach, Oregon

Few places wow like the neverending stretch of Oregon’s coast. Towering rocks surrounding by wild waters and infinite stretches of forest make the region a gem of the nation. Inside this gem, you’ll find Cannon Beach. Home to Haystack Rock, tide pools galore and only 1,800 residents, it’s the cosiest Pacific town imaginable. In addition to a gorgeous landscape, it’s home to a bustling art and gastro scene.

31. Solvang, California

Head to the historic Danish Village that is Solvang, California. Pop into one of the towns famous bakeries and get your fill of Danish pastries and then wander the many old-world style boutiques. Either way, you’re in for a heavy dose of Scandinavian charm.

30. Jefferson, Texas

The friendly come as you are attitude, pre-civil war history, charming small town eateries and family shops are what make Jefferson, Texas so special. Frozen in time, this city has plenty to offer for history buffs such as the Confederate Ordnance Magazine, the Atlanta Rail Car and several preserved homes. Outdoorsy folks will enjoy nearby Caddo Lake, one of Texas’ natural beauties.

29. Great Barrington, Massachusetts

Berkshire County’s Great Barrington is known for being one of the country’s most charming small towns. An oasis for nature lovers and art aficionados, there’s something for everyone. Sip on fresh spiced cider from a local farmer, catch a show at Mahaiwe, explore the Berkshires or grab a bite and drink at any of the charming small towns gastro gems.

28. Bennington, Vermont

Cosy, romantic and sleepy are just a few words to describe Bennington. This artsy, folksy and mega historic shire town is one of the best in the nation. Grab some goods at the local farmers market, visit the largest working craft pottery in the US and then check out the Historic Deerfield. If you’re a literary enthusiast, you will love the many dedications to Robert Frost throughout the city.

image: Four Chimneys Inn/Facebook

27. Bisbee, Arizona

Bisbee is home to a rich Apache, cavalry and mining history. Nowadays, it’s known for its thriving art and food scene, downhome vibes and charming small-town atmosphere. Whether you want to explore local galleries, get fancy with fine dining or indulge in a local pub crawl, there’s something for everyone.

image: Discover Bisbee/Facebook

26. Nantucket, Massachusetts

This former whaling village sings of the old days with its crooked cobblestone streets and sleepy harbours. While widely known as a tourist destination, Cape Cod has done an excellent job of ensuring that it doesn’t turn into a tacky vacay-town. Eat your heart out with their world-famous seafood and then take in the golden beaches.

25. Whitefish, Montana

The outdoorsy and charming small town is Montana’s best-kept secret. Bike around the quaint and cosy old town and then take a day hike starting at one of the cities many trailheads. Afterwards, head to the local art studio where you can paint pottery or make other crafts. Hungry? Don’t even get us started on the food. Take your pick from a plethora of local eateries and don’t leave without a treat from Sweat Peaks Ice Cream.

24. Chimayó, New Mexico

One of the nation’s most charming small towns is nestled in the foothills of the Sangre de Cristo Mountains. In addition to a mountain village charm, it’s home to one of the nations most important religious monuments, El Santuario de Chimayo. The Spanish Colonial church is known best for the healing soil on which it sits. In this historic New Mexican village, you’ll also find famous weavings of the Ortega and Trujillo families.

Photograph by David O. Gunter, copyright 2008

23. Skaneateles, New York

This quaint lakeside village is known for its famous art gallery and nearby nature preserves. The John D. Barrow Art Gallery is perfect for a weekend afternoon, and Anyela’s Vineyard is a real treat for winos. In Skaneateles, you’ll find a healthy amount of local shops and restaurants that only add to the charm.

22. Oxford, Mississippi

Founded in 1837, this Mississippi small town is a hotbed for artists and musicians. Commonly touted as the ‘Cultural Mecca of the South’ it has a lively and eccentric entertainment scene. Whether you want to explore the cities history or get to know local artists, Oxford has you covered.

21. Jacksonville, Oregon

Life moves a little slower in Jacksonville, Oregon. Spend the day hiking the cities endless nature trails or catch live music at any of the local bars. Even better? It’s situated right on the Apple Valley Wine Trail, so there’s plenty of great sips to be had.

20. Unalaska, Alaska

This coastal gem is the hub of Alaska’s Aleutian Islands. Seemingly in the middle of nowhere, this small harbour town is surrounded by rugged beauty and home to some fascinating history. A 10,000-year-old Unangan culture, along with local ties to WW2 are what make it a draw for history buffs.

Additionally, it’s one of the world’s most prized fishing areas. Here’s you’ll find the world’s absolute best salmon, king crab, halibut and so much more.

19. Fish Creek, Wisconsin

This picturesque Door County jewel is busting with character. It checks all the boxes for a cute small town with plenty of outdoor activities, a tightknit community and lively food scene.

18. Telluride, Colorado

Known for its world-class ski resort, Telluride’s small-town atmosphere will surprise you. The tiny town is chock-full of quirky shops and local markets. Take a stroll through their charming downtown or get schooled on their gold-rush history. Afterwards, pop into a local bar for some of Colorado’s famous craft beer.

17. Williamsburg, Virginia

This colonial town has been charming people’s socks off since 1699. Explore the local colonial history or take in the natural scenery that surrounds. Moreover, history lovers will enjoy a trip to the Jamestown Settlements and winos will love the Williamsburg Tasting Trail.

16. Moab, Utah

Tucked away in both the Arches and Canyonlands National Parks, Moab, Utah is simply stunning. Surrounded by the otherworldly beauty of the burnt orange landscape, it’s truly unlike anywhere else on Earth. In addition to stunning scenery, the local art and gastro scene is thriving. Take your pick from tons of local galleries, microbreweries, mom and pop eateries and more.

15. Jackson, Wyoming

Situated in the valley between the Tetons and the Gros Centre Range, Jackson, Wyoming is the ideal outdoorsy town. Walk under the town square’s famous antler frame and take in the stunning old west scenery that surrounds. Nature enthusiasts will love the neverending trails that lead to crystal clear lakes and alpine meadows. Grab a beer at any of their small town taphouses, and you’ll feel right at home.

14. Leavenworth, Washington

This Cascade Mountain village is straight out of a Bavarian fairy tale. Here you’ll find friendly locals lined up at local Alpine bars serving German beer and traditional Bavarian bites. The German atmosphere is charming enough, but the surrounding mountains and wineries make it even better.

13. Stowe, Vermont

Famous as a family fun Summer destination or winter hotspot for skiers, Stowe is one of America’s best small-towns. Get your fill of local fare while taking in the surrounding natural beauty with plenty of outdoor activities. Whether you want to bike, fish, or hike, there’s something for everyone.

image: Stowe Mountain Resort/Facebook

12. Maysville, Kentucky

Maysville, Kentucky is a dreamy small town famous for its history tied to the Underground Railroad. In addition to its vibrant past, it’s home to a host of farm eateries and bourbon bars. There are plenty of things to do in this Kentucky gem. Spend the afternoon exploring the Underground Railroad Museum and then head to a local microbrewery.

11. Mystic, Connecticut

This seaside village is every bit as charming as you’d expect with a name like ‘Mystic’. Tirelessly devoted to all things nautical, this cosy Connecticut town is unbelievably cute. Plenty of local festivals, markets and community get-togethers bring the place to life. Additionally, the Historic Downtown features plenty of great options for local dining, nightlife and shopping.

10. Eureka Springs, Arkansas

Situated smack dab in the Ozark Mountains, this Arkansas village is full of tight winding streets, Victorian homes, stunning lookouts and an eccentric community. Because it’s home to healing natural springs, a bumping old town and picturesque Lake Leatherwood, there’s something for everyone.

9. Carmel-by-the-Sea, California

Carmel-by-the-Sea checks all of the boxes for a charming small town. Unspoilt white sand beaches, cosy B&Bs, old-world taverns and a unique historic district. At Carmel, you’ll immediately fall for the storybook cottages and romantic coastal atmosphere. The old town is chock full of hidden gems from tiny eateries to family jewellers and the coast hosts several outdoor activities. It’s boutique businesses, stunning seaside and friendly mood makes it one of the most charming small towns in America.

8. Yellow Springs, Ohio

Built on springs thought to be healing, Yellow Springs is a cosy Ohio town perfect for R&R. Additionally, local food and surrounding natural areas add to its relaxed and homey vibe. Its allure is so infectious in fact that Dave Chappelle still calls this charming small town home.

7. Meredith, New Hampshire

Historic sites, local concerts, art fairs and fishing derbies give Meredith its small-town flair. Here you’ll find a shared sense of place, history and culture that’s unique to the town. Whether you’re looking to indulge in some local foods or explore Lake Winnipesaukee, Meredith has you in mind.

image: Smile New Hampshire/Facebook

6. Magnolia Springs, Alabama

Colourful homes, historic churches, stunning tree tunnels and inviting locals bring this charming small town to life. With only 1,000 residents, the community is exceptionally tightknit and home to plenty of neighbourhood events. This riverside village is also famous for its year-round postal delivery via water. Whether you want to explore the gorgeous trees that hang over the street or dine at world-class Jesse’s Restaurant, you’ll be well taken care of at Magnolia Springs.

5. St. Augustine, Florida

St. Augustine has all the charm you’d expect from a lively town founded in 1565 by Spanish colonizers. Despite being home to some of the nations most interesting and valuable historical sites, the city maintains a small-town charm. You’ll find the seaside village is the perfect blend of all things maritime, colonial history and community.

4. Sugar Hill, New Hampshire

Few things wow like Sugar Hill’s sweeping views of New Hampshire. This tiny New Hamshire town is known for its stunning fall foliage and annual Lupine festival in addition to its gorgeous natural beauty. Take in the meadows in the spring or fiery trees in the fall, Sugar Hill is lovely year-round.

image: Sugar Hill Sampler/Facebook

3. Big Sky, Montana

Big Sky is the rustic charming small town of your dreams. Situated at the base of Yellowstone National Park, it’s famous for its surrounding beauty. The dramatic rugged wilderness combined with the friendly nature of the locals only adds to the mountain lodge charm.

2. Woodstock, Vermont

Woodstock has all the fixin’s of a charming small town. New England character, prideful locals, surrounding scenery and unbelievably charming old town. In Woodstock, you can enjoy delicious farm to table meals, endless scenic trails and then experience its rural heritage without ever getting on a highway.

1. Stockbridge, Massachusetts

Stockbridge looks like something out of a Norman Rockwell painting, and that’s because it is! This cosy New England town was made famous by his portrayal of the city during Christmas. Stockbridge is the ideal New England small-town.

Its charming square, constant community events, historic inns, local eateries and preserved homes make it top the list for America’s most charming small towns.

Check out the Most Instagrammable Spots in Massachusetts here.

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