18 Best Places to Retire for Upper-Middle Class (2020)

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When comes the time to retire, if you did fairly well for yourself over the years, then cost may not be one of your biggest concerns when you are picking a place. So, if you consider yourself an upper-middle-class citizen, you may find yourself judging the best places to retire on things other than a low cost of living and on things such as the lifestyle it offers you.

The best places to retire for upper-middle-class citizens are those that have a thriving senior community, plenty to do around the city, and a relaxing lifestyle. Some of the most popular places for seniors to retire include Ocean City, New Jersey, Cheektowaga, New York, and Easton, Maryland.

If you are curious to find out more about some of the best places, you can retire all around the United States and what each of them will have to offer you in your time of retirement, keep reading the article below to find out more.

Portland, Maine

Portland is one of the largest cities within The Pine Tree State of Maine. It provides you with gorgeous outdoor scenery filled with trees and plenty to do in your spare time. This includes visiting museums such as the Portland Museum of Art, sightseeing around the city in places such as the historic district of Old Port, or going on a boat cruise around the Casco Bay.

On top of all of the fun that this city will offer you in your free time as a retiree, it overall provides you with the perfect place to settle down. You will experience the beauty that every season has to offer. Be around an increasing senior population where you can make plenty of friends and rest assured knowing that, according to WalletHub, they have the best healthcare in the United States.

All in all, the state of Maine and the city of Portland is a gorgeous and relaxing place to retire, and to top it all off, ranks as one of the safest states to live within the United States.

City Population: 66,417

Population That is 65+: 13.8%

Cost of Living: 108.2

Boston, Massachusetts

According to the site BankRate.com, the popular city of Boston is the 2nd best place to retire even though the cost of living is about 60% above the average of the United States.

Although, if you can afford to live in the urban environment that Boston provides, it is a great city to settle down in terms of lifestyle and amenities. Not only are there plenty of parks and restaurants, but there are also other fun places to visit, such as the Museum of Fine Arts and plenty of shows at the theater.

If you choose to retire in Boston, you are sure to find a home in a gorgeous neighborhood that provides you with plenty of opportunities to walk around your community. Additionally, Boston has great means of transportation so you can easily get around and some of the best medical facilities in the U.S. so you know you are taken care of.

City Population: 694,583

Population That is 65+: 11.2%

Cost of Living: 162.4

Denver, Colorado

If you are looking to live in an urban and lively city, Denver, Colorado, is a great place to consider for your retirement. Denver, Colorado, not only offers the sight of the stunning Rocky Mountains but has plenty of activities for you to spend your time. They include visiting plenty of museums infused with history, catching a game at one of the sports fields, or visiting a zoo or watching aquarium animals.

So, if you are okay facing the mild temperatures Denver can throw your way in the winter in exchange for walking on some gorgeous hiking trails and having the opportunity to spend the many sunny days you have outdoors, then this city is perfect.

In terms of healthcare, they have a lot of medical facilities with more than 24 health care facilities for every 1,000 senior residents, which adds up to be more than the U.S. average.

City Population: 716,492

Population That is 65+: 11.4%

Cost of Living: 128.7

Reno, Nevada

While you may immediately think of gambling or music venues when you think of Reno, Nevada, the city has much more to offer than nights out on the town, although always having something to do is a pretty great perk of living there. Overall, the city provides you with a small-town feel but gives you many of the amenities a big city would have, and many retirees currently love it.

You will also have plenty to see near Lake Tahoe or the Sierra Nevada mountain range, where you can take out a boat, go on a bike ride, hike around the paths and break out your pair of skis in the winter.

To top it all off, Reno, Nevada, also does not charge any income tax, so while you may be spending a bit more because of the higher than average cost of living, at least all of your retirement income will be yours to keep.

City Population: 250,998

Population That is 65+: 14.4%

Cost of Living: 116.2

Cheektowaga, New York

Cheektowaga is a popular choice if you are looking to retire in a place that offers a more suburban lifestyle or just want to be close to the NHL Buffalo Sabres or NFL Buffalo Bills games that happen throughout the year. You’re also not too far from the water in this city if you wish to make a weekend trip out of visiting Lake Erie or Niagara Falls, which offer some beautiful sights.

This city also has plenty for you to do in any of the seasons and is especially great if you love spending time on the mountains skiing or snowboarding. The best part is that the cost of living and average house prices are quite affordable. With the median home price being $136,100, as an upper-middle-class citizen, you can choose to splurge and get more bang for your buck.

They also have a larger senior population than most, suggesting the opportunity for you to make plenty of friends in your retirement.

City Population: 86,181

Population That is 65+: 19%

Cost of Living: 83.8

Ocean City, New Jersey

Ocean City is one of the most appealing cities to retire within the Garden State, and it is by far one of the best for those who plan to have family visiting frequently. They have plenty of beaches, a fun boardwalk with plenty to entertain both you and your grandkids with, and if you feel like gambling, Atlantic City is only a short drive away.

New Jersey is also home to some amazing food, including hoagies, hot dogs, saltwater taffy, and more!

However, living in this city does not come cheap, so unless you are ready to pay almost double what you see, most median home prices in Ocean City may just cost a little too much for what you want to spend. If you can, though, you will not be disappointed as the thriving senior communities and summer days by the beach make it worth every penny.

City Population: 6,927

Population That is 65+: 31.6%

Cost of Living: 150.6

Tampa, Florida

If you are looking to retire somewhere by the beach that has warm weather all year long and still is able to be a part of the city life, then Tampa, Florida, is for you.

The best part of it is that it comes all at an affordable price as Florida is one of the seven states that does not charge income tax, so your retirement income can be stretched the farthest if you choose to retire there.

Tampa is also filled with loads of places to keep you entertained, whether you love a nice stroll around the city, want to go to a zoo or aquarium to see some animals, or venture off to see a sports team play or do some shopping. In addition to all that, if you plan to do some traveling once you retire, there is a cruise ship port in Tampa, making it easy to cruise around the Caribbean or Europe.

Overall, making this a perfect destination for your retirement would save your income for vacations and not spend too much of it on a home or on the cost of living.

City Population: 399,700

Population That is 65+: 12.3%

Cost of Living: 100.1

Easton, Maryland

With a large senior community, this history-filled and charming town of Easton, Maryland, is a perfect place to have a relaxing retirement. Here you can enjoy some amazing dining, do plenty of boutique shopping and see plenty of galleries or attractions around the town. In fact, it is actually recognized as one of the Arts and Entertainment Districts in Maryland, making it an exceptional place for artists to live and sell their art.

You also would be living right off the Chesapeake Bay, so in the warm summer months, you have plenty of opportunities to do some fishing, boating, canoeing, or kayaking if you are someone who loves spending time outdoors.

Let’s say that the city of Easton was meant for you in your retirement if you were looking to have a calm retirement in a small town and don’t mind the cold that the winter months may bring.

City Population: 16,671

Population That is 65+: 23.7%

Cost of Living: 106.7%

Corvallis, Oregon

If you are looking for a laidback kind of retirement and would rather spend more time relaxing than anything, the small city of Corvallis offers you just that. It was made for the wine connoisseurs who love to explore different wineries or the beer drinkers who love exploring the roots of a good beer, but most of all appreciate the slow-paced life and gorgeous scenery that the city provides you.

If you also are an outdoor lover, there are plenty of things to do in nature in Corvallis, including getting some physical activity in one of the many biking or hiking trails or taking the time to be by the water and do some fishing.

Another one of the most popular things this city has to offer is a farmers market, so if you love spending your Saturdays strolling around town, this small city in Oregon is a great choice for your retirement.

City Population: 56,224

Population That is 65+: 12.1%

Cost of Living: 112.8

Burlington, Vermont

If you want to see the gorgeous Lake Champlain and take in plenty of trees on your daily walks around the city, then Burlington, Vermont, is the place for you to retire. So, if you don’t love the outdoors, then you may want to consider retiring elsewhere. This city is packed with activities for you to do out in nature, including biking along the Burlington Bike Path or walking around the town.

You can also spend your free time shopping amongst the Church Street Marketplace, take a ferry from Lake Champlain to New York if you are up for an adventure, visit the farmers market when you’re free, or spend time at a zoo or an aquarium seeing some animals. Then when the weather starts to get a little cooler, you can spend your time exploring the handful of distilleries around the city—all in all providing you in your retirement with plenty to do.

City Population: 42,819

Population That is 65+: 11.7%

Cost of Living: 111.5

Omaha, Nebraska

Omaha provides you with a much lower cost of living than some other places on this list, as it is approximately 10% lower than the U.S. average and has much lower housing prices. However, the most attractive feature may just be the quiet, residential neighborhoods you can have at home but the ability to head to the city and be entertained.

With plenty of shopping and entertainment, Omaha is great for those who always want to have a relaxing retirement but the option to do things here and there.

Whether you want to spend time at the Old Market, visit the Henry Doorly Zoo or visit the Freedom Park Navy Museum, there is an assortment of activities to do around the city. You can also just spend your day exploring the town as the walkable Aksarben-Elmwood park is only 15 minutes from downtown, which has stunning Tudor Revival homes and a thriving shopping and dining community to enjoy.

City Population: 478,192

Population That is 65+: 12.6%

Cost of Living: 89.8

Appleton, Wisconsin

According to USAToday, ranking within the top 30 best cities to retire in the midwest is Appleton, Wisconsin. The high number of physicians per 100,000 residents and plenty of activities for seniors, including theatres, golf courses, recreation centers, and plenty of restaurants.

While the town may not provide a whole lot of adventure, there is plenty of history to be explored at their museums like the Hearthstone Historic House Museum and plenty of places to explore nature such as the Gordon Bubolz Nature Preserve. In Appleton, you are also pretty close to Lake Michigan if you ever wanted to drive out there for a day.

If you were looking for a safe and clean city to slow down, spend some time outdoors and save some money when it comes to housing in your retirement, Appleton is the city that can provide you with that.

City Population: 74,098

Population That is 65+: 13%

Cost of Living: 84.9

Cody, Wyoming

If the Cowboy state of Wyoming does not get you excited by the fact that there are no income taxes, the low property taxes, highly increasing senior community, and large number of healthcare physicians sure will. This gorgeous state was made for anyone who loves spending their time outdoors.

In Cody, some of the fun stuff you can do in your spare time includes exploring the Old Trail Town, visit the Dead Indian Summit Overlook, visit the Beartooth Basin, get to do plenty of horseback riding, go fishing and see some amazing sights. Outside of the city, the number of places to visit only increases as Wyoming has plenty to offer.

However, if you live in Wyoming, you will have to be okay dealing with some strong winds and thunderstorms at times. However, the 222 sunny days throughout the year and the space this city provides make it worth spending your retirement there.

City Population: 9,788

Population That is 65+: 20%

Cost of Living: 104.8

Providence, Rhode Island

If you love being able to walk around the city you live in, then the attractive downtown of Providence, Rhode Island, will appeal to you as a place to retire. This city is also known for its plenty of colleges and the world-renowned Rhode Island School of Design. So, if you are a retired academic or artist, there will be plenty for you to do as the schools tend to host events, including performances, opportunities to learn, and gallery nights.

There is also plenty to do around the city, including visiting the Roger Williams Park Zoo to see the animals or going to the Historic Federal Hill, which has plenty of shops and dining for you to enjoy. They also have plenty of cool tours that you can go on, including boat tours, kayak tours, or a chance to taste wine while on a boat through the Providence waterways.

City Population: 179,883

Population That is 65+: 10.2%

Cost of Living: 105.1

Ann Arbor, Michigan

If you love the feel of a small-town environment, then considering the city of Ann Arbor in Michigan state is a great way to have a pleasant and relaxing environment. The city of Ann Arbor, home to the University of Michigan, is not all about the students, as it has plenty to do in the downtown area, including dining, entertainment, artistic performances, as well as a variety of stores and adorable cafes.

Some other things you can do around Ann Arbor include exploring nature at the Matthaei Botanical Gardens, visiting the Ann Arbor Hands-On Museum, and seeing some sights and landmarks such as the Law Quadrangle or even see a show at the Michigan Theater. Overall, providing you with plenty to do both outdoors and indoors.

If you want to know more about the city of Ann Arbor, you can watch this video that was made by Pure Michigan:

City Population: 119,980

Population That is 65+: 11.5%

Cost of Living: 117.5

Hilo, Hawaii

If the fluctuating weather that comes along with the four seasons does not seem up your alley and if you are just looking to retire in a place that feels like you are on a constant vacation, Hilo, in Hawaii is the best place for you. This city has plenty of gorgeous beaches, warm sunny weather but all at the price of a more than average cost of living.

All in all, though, if you are looking for a quiet, calm lifestyle where you get to know your community as well as be able to explore waterfalls such as the Rainbow Falls, explore the rainforests, or venture around Hawaii Volcanoes National Park, you can do all that in the city of Hilo.

On top of it all, there are plenty of seniors to mingle with and some amazing shops, restaurants, and galleries to spend time when you decide to go downtown.

City Population: 45,703

Population That is 65+: 19.5%

Cost of Living: 130.3

Carlsbad, California

Another great retirement option that guarantees you warm weather year-round is Carlsbad, California. On top of that, they have some gorgeous housing available in some very attractive suburbs if you can afford it as the cost of living is about 90% higher than the U.S. average. It is common for places within California to cost a little more.

This part of the San Diego metro area has more senior residents and provides you with the best of both worlds as you can feel as though you are part of a small-town while also being close to all the big-city amenities just along the coastline.

You also get the opportunity to do plenty in your free time as there are over 30 parks and over 50 miles (80km) in hiking trails allowing you to spend all your time walking around some stunning places. This includes the Denk Tank Mountain at the Rancho La Costa Preserve, which is the highest place you can find in Carlsbad, allowing you to see an aerial view of the city.

However, the fun doesn’t end there as there are beaches, flower fields, amusement parks, museums, plenty of places to shop, farmers’ markets, aquariums, and basically everything under the sun that allows you to be always entertained during your retirement.

City Population: 115,382

Population That is 65+: 16.8%

Cost of Living: 191.7

Middletown, Connecticut

The last on our list, but certainly not the least, is the northeast Connecticut city of Middletown. While it is a bit of a college town, this comes with its perks as it means there is no lack of restaurants, places to shop, or cultural attractions.

However, one of the best perks of being near Wesleyan University is that they offer no-credit courses for anyone in the community and come at a low cost. So, if you need a way to spend your time and love to learn, attending the Wesleyan Institute for Lifelong Learning is the best way to do so.

You can also visit some gorgeous places outdoors, such as the Wadsworth Falls State Park or Harbor Park. Even some fun places indoors such as the breweries. All in all, Middletown is a well-rounded city for the everyday folk looking for a calm place to retire.

City Population: 46,258

Population That is 65+: 14.5%

Cost of Living: 101.4%

Final Thoughts

As an upper-middle-class citizen, the cost of where you are retiring and how much a home costs may not be at the top of your list for priorities when comes the time to pick a place to retire. So, you may be more interested in the lifestyle the place you are going offers you and the senior community that exists or doesn’t exist.

Through our list of the best places to retire, you can get a look into some of the most popular cities to retire in and hear about some of the amenities in that area and the pace of life it provides.

At the end of the day, though, what matters the most is ensuring that you pick somewhere that you know you will feel at home, so it is good to know all about the city you are going to before committing to living there for the rest of your life.

18 Best Places to Retire for Upper-Middle Class