The Brainy Penny States That Will Make You Regret Retiring There – TheBrainyPenny
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States That Will Make You Regret Retiring There


Don’t call the movers yet!  Did you know that deciding where to retire could be as important as the financial planning you put into preparing for retirement?

Your retirement destination will determine how much you will need to pay in taxes; your living costs and health care options, factors that are state specific.

Will you head to a year round sunny destination or enjoy the change in the seasons?




Delaware, that small mid-Atlantic state with dune-backed beaches bordering the Atlantic Ocean, Delaware River and Delaware Bay.  You can find many quaint towns, stroll the boardwalks visit art galleries and yes sit in constant traffic traveling north or south on DE-1 to Rehoboth, Bethany, Dewey and Lewes Beaches.  Don’t follow the shortcut on Purgatory Swamp Road!

While the state welcomes hundreds of shoppers daily who revel at the tax-free registers, the cost of living isn’t that cheap,  If you choose not to live near the beach towns, the home prices in moderate neighborhoods are currently at $300,000 and rising.  You will need at least one car to frequent the strip malls, supermarkets, restaurants and medical facilities, as there is no public transit in Delaware.  Access and quality of the local health care system is mediocre at best.

2. Texas

Howdy!  Are you comfortable with the western look?  Then pack your cowboy hat and boots, leather belt and worn in blue jeans.  Bring your appetite to plenty of barbecues, feast on fried goodies and top off your meal with a visit to a Blue Bell Creamery for family made ice cream.  The varying landscapes of Texas offer trips to coastal plains, prairies, lakes, deserts, the famous Rio Grande River and refined cities like Houston, Dallas and Austin.

Seniors looking to retire her should be aware of the state’s health care issues.  Texas has the third worst physical to patient ratio in the country, with access to specialized care being difficult.  Nursing homes are poorly staffed and they hold a record for having the most concerns called into a hotline.


3. Oregon

The crown jewel of Oregon is the city of Portland. Known for its quirky, avant-garde culture and home to iconic coffee shops, boutiques, farm-to-table restaurants, art museums and microbreweries, Portland is the place to be.

But Portland and other popular cities along the coast have seen a 7.5% increase is housing costs in the past year.  Shoppers you’ll be thrilled that there is no sales tax.  If you relocate on the west coast of Oregon don’t forget to bring an umbrella, raincoat and boots.

The average precipitation for the year is 200 inches! Unfortunately there have been extended periods of smokey skies due to the long-lasting forest fires nearby.


4. South Carolina

You may be looking forward to teeing off at one of South Carolina’s plush golf courses or soaking up the sun at Myrtle Beach.   Maybe you’re looking for a slower paced life in a southern city like Charleston.  Before you make the decision to retire here, there are some issues to consider.

The cost of living in South Carolina is more than 7% lower than the national average and so are the salaries.   This results in unequal access to health care in a state that is already ranked in the top ten for obesity.  In recent years South Carolina is among the worst states for violent crime.

If you have a good retirement income and South Carolina’s small town appeals to you, then you can find some safe and affordable homes in suburban neighborhoods like Wellford (estimated home values $80,000) or Edgefield. ($90,000)

5. Michigan

Michigan residents can enjoy the natural beauty of the states wilderness trails and explore the epic Dow Gardens with the longest canopy walk in the nation. The state’s coastline offers tons of outdoor fun as it welcomes four of the five Great Lakes on its borders.

The downside for retirees that choose to reside in this state are the long and dangerous winters.  Have you ever heard the term “lake-effect snow?  Well, the short version is the Great Lakes have a higher intensity for heavy snowfalls.  In some years, meteorologists have recorded from than 100 inches of snow in a winter season.

So. . . pack your shovels, dodge the potholes and be prepared to pay a premium for car insurance.  If you’re thinking of using public transit you will be disappointed. It is underfunded and underdeveloped.

6. Tennessee

Country music fans will have a grand old time relocating to Tennessee.  The heart of country music, the Grand Ole Opry, the Country Music Hall of Fame and Museum are nestled in Nashville.  Take a short drive to the southwest to visit Elvis Presley’s Graceland.

With savings and a good pension, you can enjoy a secure retirement here. The downside is Tennessee’s health care as it is in shambles.  The lack of federal health care funding and increased costs of medical procedures has resulted in a reduced number of hospitals.

Crime is also a problem if you live in Memphis, the fourth most dangerous city in the country.  Maybe the plan should be to settle near the Great Smoky Mountains and enjoy the local wines and whiskies.

7. Illinois

Illinois offers seasonal adventures year-round.  There are magnificent state parks, miles of hiking and biking trails and rivers to explore.  The suburbs are surrounded by farmland, which means plentiful farmers’ markets with organic produce in the summer and fall.

The big attraction is the windy city . . . Chicago.  With towering skyscrapers, music festivals, ethnic restaurants and access to Lake Michigan Chicago is a lively place to be.  The downside is the states tax base.

Although senior citizens receive an annual rebate, the property taxes are hefty and can significantly drain retirement funds.  Shoppers won’t be happy paying an 8.19% sales tax at the register.

8. Georgia

Best known as the peach and peanut growing state.  Georgia offers urban city amenities in Atlanta, beach towns, mountains and lakes to explore.  Savannah will dazzle you with is famed 18th and 19th century architecture and is vibrant public parks.  Annually, April brings the Masters Golf Tournament to Augusta.

Over the last two decades suburban neighborhoods have been expanding rapidly causing traffic congestion in Atlanta that matches Los Angeles.  This has created a serious smog problem.   The cost of medical care is comparatively low in Georgia.

However, their health care system is struggling with funding problems resulting in several hospitals shutting down emergency rooms of entirely closing.

9. Alabama

Sweet Home Alabama! This southeastern state is home to white sand beaches, beautiful lakes and rivers and red-clay hills.  Avid golfers can save private membership fees by teeing-off at the numerous and well maintained public golf courses.

If you do choose to retire to Alabama, make sure your home has a shelter where your family can stay safe during the peak tornado periods.  Your savings will go farther here since they have a lower than average cost of living.

Alabama has a long on ongoing history with racial and gender discrimination so you may want to look elsewhere if you believe in diversity.

10. Connecticut

Connecticut is a picturesque New England state with a mix of coastal cities, small towns, rural areas and magnificent lakes.  Mystic Seaport Aquarium and Museum are two must visit destinations.  The high cost of living might dissuade people from retiring in Connecticut.  Residents pay both hefty sate income taxes and high local property taxes.  The state is in a budget crisis as many large companies such as General Electric and Aetna have relocated, resulting in a huge loss of financial contributions to the tax base.  Retirees can expect to see escalating tax bills during their golden years.

11. Indiana

Looking to retire to a state that has a four-season climate?  From May through October, Indiana has festivals for everyone!  Music lovers can attend blues, country and jazz concerts.  County fairs, flea markets and art shows can be found countywide.  Racing enthusiasts will want to head to the Indy 500 in May.  For retirees the state doesn’t tax social security benefits and the property taxes are relative low, which is good news.  But Indiana is home to tornado alley!  The EPA reports that Indiana is one of the worst water polluting states as its industries release toxic chemicals into the water.

12. Maryland

This Mid-Atlantic state has a lot to offer tourists from the Ocean City Beaches and amusement park, to the Chesapeake Bay lighthouse and Maritime Museum and the Baltimore Harbor and National Aquarium and Science Center.  Retirees should be cautious about relocating to Maryland.  The state government has high taxes and recently increased the gas tax and inheritance tax.  Housing prices in safe neighborhoods are steep and living near the coast could wipe out your savings when you’re charged a premium for flood insurance.


Road Trip! Home to the birthplace of the blues, the Mississippi Delta is a region filled with places to explore.  Residents of Mississippi endure long hot, humid summers and are rewarded with warm temperatures, averaging 50 degrees in the winter.  There is little to no snowfall, but late summer and early fall always bring a risk of damaging hurricanes.  Mississippi is among the states with poor health care quality being strained by the high obesity rate and epidemic numbers of opioid users.

14. Oklahoma

Oklahoma offers a diverse landscape with expansive plains, hills, lakes, forests and 33 state parks. This state has a mixture of western history, Native American culture and Southern charm.   Oklahoma City and Tulsa offer city vibes and a slower paces life style.  Storm chasers are sure to frequent Oklahoma since it is infamously part of Tornado Alley.  You can expect battles with Mother Nature from March to May.  As a result, the roads and bridges are in need of major repairs, taxing the states budget.  The housing and taxes are affordable, but seniors should be concerned that the doctors setting down roots in Oklahoma are decreasing.

15. California

California has a wealth of interesting and inviting cities.  Enjoying an excursion to Napa Valley or Sonoma for wine tasting, hiking in Yosemite National Park and photographing the iconic vistas, cliffs and waterfalls and of course a spectacular ocean drive down Rte. 1on the west coast.  It’s a great state, but you certainly don’t want to retire here. California has the second highest cost of living expenses in the U.S.  The state’s sales tax is the highest the country and other tax burdens will drain your retirement dollars.

16. Alaska

There is no denying that Alaska has some of the most breathtaking wilderness areas and wildlife viewing in the country. Where else can you go fishing, hike to see a glacier up close, eat reindeer steaks and see moose wandering around like feral cats? Alaska is perhaps the vacation of a lifetime, but it’s probably not the place you want to spend your golden years. The cost of living in our 50th state is very high, since almost everything except wild game must be flown in from the continental US or other countries. It’s true that state and city taxes are low, but health care is very expensive, with most residents choosing to fly to Seattle for non-emergency operations to save big bucks.

17. New Mexico

New Mexico bills itself as “The Land of Enchantment” and while that might be true for visitors, it’s anything but enchanting for retirees. Housing is very expensive, especially in large cities like Santa Fe, where the average housing cost is 20% above the national average. Beautiful Las Cruces, known for its festivals and abundance of chili’s, has some of the highest violent crime rates in the US. While the warm sunny climate appeals to many, the downsides of living here on a fixed income outweigh the sunshine.

18. Rhode Island

Rhode Island has so much to offer at first glance; beautiful beaches in the summer, white winters for the holidays, not to mention the seafood platters that are too good to ever pass up, but high taxes and cost of living leave this state out in the lurch. This state has some very nice cities, such as Newport, that are ridiculously expensive and other cities, such as Providence, which offer a lack of anything even remotely entertaining. As small as it is, this state has some of the highest electricity prices and worst transportation system in the country. While it does offer great health care services, you might want to reconsider making this your retirement abode.

19. Kentucky


What does the word Kentucky bring to your mind? Whiskey? Blue grass? Horses? All of those and the tax breaks this state offers retirees make this state sound appealing but hold your horses! Before you consider this state to spend your retirement years, consider that healthcare costs for the average retired couple are some of the highest in the country. Most of the state has devastating levels of poverty, leaving most of the state without much to offer seniors. So, while the overall cost of living and taxes are very low, think twice before committing yourself to this state, especially if you have serious health issues.

20. Arkansas

You might hear people who have visited Arkansas gush about the beautiful hot springs and miles of unspoiled natural beauty, but there are a few things to consider first before you make that retirement move. First, while the state does have a very low cost of living, it’s been rated by some groups as being the absolute bottom of the barrel when it comes to quality of life. This might be because of the very high crime rates and horrible summer humidity, which brings with it hordes of mosquitoes. If you own stock in companies that sell air conditioners and DEET, this state might be perfect for you. Otherwise, take a second look.


21. New York

New York is one of the most exciting states you will ever want to vacation in, but it might be dead last when it comes to retiring there. First, no matter where you live, the cost of living in this state is at least 29% higher than the national average. If that weren’t bad enough, it ranks next to last when it comes to lists of quality health care and quality of life for seniors. Consider making New York a vacation destination, rather than a retirement destination, unless you have plenty of cash lining your pockets.

22. Hawaii

This state is another vacation must see but the super high cost of just about everything will put a real damper on most retiree’s budgets. The islands must have almost everything, even basics like toilet paper, flown in from other locations. Hawaii also takes first place when it comes to the highest gas prices in the US. There are beautiful beaches, mountains, and volcanos to be sure, but the very high prices, continual influx of tourists, overcrowding and volcanic smog make this a nightmare of a place to retire for most people.

23. West Virginia

Remember John Denver’s song Take Me Home Country Roads? Denver crooned that it was “almost heaven, West Virginia” and this was most likely because he didn’t retire there on a fixed income. This pretty state is known for whitewater rafting, charming old -time cities like Charleston, and with a cost of living running 3% below the national average, it sounds like a great retirement state, until you find out that the state has very high health care costs, no to mention high crime rates. This is most likely due to the poverty that affects most cities due to the closing of coal mines. West Virginia has a lot going for it, just not for retirees.

24, New Jersey

Anyone who has visited New Jersey knows that the Garden State has some seriously charming little towns and fun beach cities, but unless you are living to golf every day, this state doesn’t have much else to offer retirees. New Jersey has the second highest state and local tax rate in the US. It also boasts some very high prices when it comes to real estate, with the average house price hitting more than $311K! The cost of living in this beach state is 22% above the national average, which can leave many retirees out in the cold.


We don’t want to pick on Louisiana, but let’s be frank about a few things, shall we? While the incredible music scene and food are something everyone should experience, living here leaves a lot to be desired. With Category 4 and 5 hurricanes making regular appearances every summer, not to mention the suffocating humidity, the weather is not something to crow about. Louisiana has a high tax rate of almost 10% and the second highest crime rate in the US. Let’s not forget alligators and a pathetic health care system. This state has a great deal of southern charm, but charm won’t pay the bills for retirees.

Don’t call the movers yet!  Did you know that deciding where to retire could be as important as the financial planning you put into preparing for retirement?  Your retirement destination will determine how much you will need to pay in taxes; your living costs and health care options, factors that are state specific.  Will, you head to a year-round sunny destination or enjoy the change in the seasons?

Lisa Brown

Lisa Brown

I've spent the past 5+ years as a freelance writer covering personal finance and tech. Originally from Texas, but happily living in New York City. Making money is the easy part, keeping it is very difficult!