Ah, retirement. When you can make your own decisions, choose where you live and for how long, and can finally buy that “nice” furniture. But how do you choose where to live? Some want to return to their hometown, some want to live in a big city, and still others want a nice hometown feel. For the latter crowd, we have this list of the best small-town feel places to retire.

There are a few challenges when considering your retirement location. And, even though some military families have been dreaming about this day since first receiving orders, the choice can be intimidating. When you factor in the average age of a military retiree and compare it to the civilian retiree, you’re going to get different “retirement living” options. And, of course, we’ve seen a bunch of different places, making the choice difficult.

But, we’re here to help – partly because we’re starting our retirement dream sheet too – and we’ve selected cities that show off their energy, creativity, and things to do. Just minus the stifling atmosphere of a clogged, over-trafficked metropolis. So if you are retiring from the military and looking for a cozy spot, we have compiled a list of the best small-town feel places to retire, with towns that also include a great cost of living, fewer people, and awesome amenities.

24 Best Small-Town Feel Places to Retire

Madison, WI

Don’t sacrifice culture for a lack of traffic and crowds. Madison provides all the flair of a big city without the headaches of traffic, crime, or a light wallet. Madison was on Forbes 2018 best places to retire list due in part, to it’s thriving downtown and stable economy.

Bozeman, MT

Reap the benefits of hospitality and consider the friendly charm of Bozeman, Montana. The city has been revitalized from its sleepy beginnings as just a cowboy town, and now finds itself on many Dream Towns lists. It’s quickly becoming a hotspot for all personality types, entrepreneurs and fishermen alike.

Niantic, CT

The cozy, seaside town of Niantic is sure to appease any family who loves the water. Enjoy sailboat races and an array of water activities on the city’s own piece of Long Island. And when Niantic gets a little too quiet, you’re only two hours from Boston and NYC.

Cheyenne, WY

If you’re looking for some more alone time, consider the state that has only six people per square mile. Enjoy all the outdoor distractions of Cheyenne, such as hiking, fishing, and horseback riding, without too many people getting in your way.

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best small-town feel places to retire

Hood River, OR  

Affectionately known as Portland’s backyard, Hood River is a small town with a big taste for trendy. The picturesque spot offers great hiking, friendly locals, and an assortment of craft breweries.

Bisbee, AZ

Rumored to have the best year-round climate on Earth from its unbiased residents, Bisbee has elevated itself from an old copper mining town to an affordable, eclectic town for students, writers, artists, and others trying to flee the big cities.

Bonus: Bisbee isn’t too far from Fort Huachuca, where retirees can still utilize the pharmacy and medical facility.

Greenville, SC

An undiscovered gem similar to Asheville, NC circa 2010, Greenville is a walkable and charming city yet to be stampeded. But leave your mark on it soon before the rest of the world realizes it’s the next Asheville.

Burlington, IA

With winding alleys, sloping hills, vintage record shops, and wine bistros, Burlington is the perfect balance of slowed down life sans the bore. For the adventurous, Burlington is host to the “crookedest” alley in the US, named Snake Alley.

Metairie, LA

Boasting a low cost of living with a high dose of nightlife, Metairie walks the perfect line between big city and suburban life. Besides, the actual big city, New Orleans, is just a short drive away so you don’t even need to miss it.

Elk Grove, CA

Located just outside the expensive bubble of Sacramento, Elk Grove is safe and affordable, with all the bonuses of mild winters, a myriad of golf courses, and miles of parks to play with.

Bonus: The public schools here are ranked very well if you are retiring with school-aged kids.

Charleston, SC

Fall in love with the historic charm of small-town Charleston. Settle into Southern life and enjoy the architecture, mild temperatures, and top-rated restaurants this city has to offer.

Burlington, VT

If you aren’t afraid of the cold, this Burlington can warm you with its easy access to world-class skiing, sailing, and other outdoor activities. The beautiful blend of businesses, public transportation, and parks earns it a spot on our list of best small-town feel places to retire.

RELATED: 5 Tips for Finding a Home at Your New Duty Station

Athens, GA

A hub for culture and music scenes, the artsy and the architecture aficionados are welcome in Athens. With plenty of space for both to immerse themselves, there is even still room for a 300-acre state botanical garden. And, college football of course. Go Dawgs!

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best small-town feel places to retire

Bellingham, WA

If you don’t mind a little rain, Bellingham offers eco-conscious locals an active town without the hustle of nearby big cities like Seattle or Portland. If you love simple things, or just want easy access to Canada, this is your spot.

Portsmouth, NH

The epicenter of culture, Portsmouth offers everything from historic buildings to art galleries to jazz clubs. If you can’t pick a favorite hobby, settle in Portsmouth where you can take your time discovering what wets your whistle, all the while enjoying the leisure of life in an idyllic New England town.

Bloomington, IN

This city isn’t your typical retirement city, considering its heavy inundation of progressive Indiana University students, but it has a cost of living below average, a small population, and plenty of recreational activities. Bloomington is—wait for it—budding with promise as your new spot to put down roots.

Beaufort, SC

Chock full of charm, Beaufort has all the bases covered for small-town living, complete with elegant storefronts, a National Historic Landmark District, boutiques, and downtown restaurants. Unwind in the city that made the top 10 of Smithsonian’s Best Small Towns.

McKinney, TX

This town in the Lone Star State provides all the notches for those looking for a small-town feel. Boasting a quaint historic district, ample space with parks, and a location just minutes from big-city amenities, McKinney has quite a few perks going for it.

Bonus: Texas has no state income tax, which means no tax on military retirement pay either!

Mathews, VA

Taking up just 84 square miles, Mathews puts the small in a small town. But it scores big on the livability factor: the revitalized historic downtown area, an array of dining options, and prime location on the Chesapeake Bay shoreline.

RELATED: Living Like a Local: 9 Best Brunch Spots Near Camp Pendleton

Eureka Springs, AR

Looking for that old-fashioned kind of small-town charm? Nestle yourself down in the Ozarks, catch a ride on the downtown trolley system and enjoy the music and arts scene throughout Eureka Springs.

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best small-town feel places to retire

Montpelier, VT

Defining small-town living, many of Montpelier’s downtown establishments are actually owned by the residents themselves. Bookshops, boutiques, and antique stores complement craft beer bars, coffee shops, and fine dining restaurants and will make anyone wonder what’s great about a big city.

Sedona, AZ

Emerging as a mecca for southwestern art and culture, Sedona ranks high on Fox News Travel’s Best Main Streets list. You may have to share your new town with tourists, but you’re rewarded with access to 200 miles of hiking and biking trails, plus the unparalleled views Sedona has to offer.

Galena, IL

Escape the stress of the big city with the help of cozy, brick storefronts, large bayfront windows, trolley cars, and wineries. Casper Bluff and Horshoe Mound are some favorite outdoor places to visit. Galena will wow you with the simple things.

Heber City, UT

This small town has a lot to brag about. There is a goldmine of amenities such as boating, horseback riding, golf, snow skiing, and hiking, Heber City has a very low crime rate and a top-notch health care system. The arts scene thrives with festivals, theatrical performances, and Native American celebrations, but doesn’t forget about what makes a small town a small town: the annual county fair.


Which one of these meets your requirements of the best small-town feel places to retire? Or you have a town to add to our list? Let us know!

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24 Best Places To Retire With A Small Town Feel
best small-town feel places to retire

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