For many people, retirement is a time of newfound freedom. Many retirees have the luxury of choosing where they want to live based on their own interests—not the demands of a boss or the needs of a teenager.
Whether you dream of a town next to the great outdoors, a city full of cultural experiences, or a place that never gets cold, your hunt for a retirement location is driven by specific desires and deal-breakers. But although you may know what you want in a home base, you may not know where to find it.
Here are 10 towns to inspire you on your quest for the perfect place to live.
You Love Culture: New Haven, Connecticut
You want a home where you can experience diverse cultures in the form of food, art, music, theater, or simply meeting people from all backgrounds and walks of life. FiveThirtyEight calculated that New Haven, Connecticut, is the U.S. metropolitan area that comes closest to representing the country as a whole in demographic measures such as “age, educational attainment, and race and ethnicity.”
But you don’t need to know the stats to recognize that New Haven has a diverse and cultured population. The city’s tourism guide boasts that local restaurants offer cuisines from “Ethiopia, Asia, Austria, France, Greece, Mexico, Japan, Cuba,” and more. Every summer, New Haven hosts the International Festival of Art and Ideas, where fans of the performing arts or topical panel discussions can find food for thought. And the local government strives, through efforts such as the Cultural Affairs Commission, to support and expand awareness of the arts and cultural expressions across the city.
As a bonus, the Elm City is just a few hours drive or ride away from New York, Boston, and other cities and towns where creative and curious people gather.
You’re an Aesthete: Savannah, Georgia
You love being surrounded by beauty, whether it’s found in nature, architecture, or design, and you want to live where every stroll around the block takes you past lovely historic homes with delicately-wrought balconies and every drive down the street is a journey under a canopy of trees. The so-called “Hostess City” welcomes residents and visitors alike with its pastel-hued buildings, cobblestone streets, and tranquil parks.
There’s a lot of beauty to explore here, from the old warehouses along the Savannah River, now repurposed as shops, inns, restaurants, and bars, to the famed squares where fountains burble and trees drip with Spanish moss. Whether you prefer to admire the graceful architecture of old homes in historic neighborhoods or to escape to the sand dunes of Tybee Island, Savannah will not disappoint.
You’re a Wine Drinker: Greenport, New York
You want to spend your weekends sipping quality wines at beautiful vineyards and generally enjoying the scenery typical of a wine-producing region. But you don’t want to live in a rural area, or spend hours traveling to visit just a few wineries. Consider the village of Greenport, located in the town of Southold on Long Island’s East End. Greenport’s maritime history and walkable streets make it popular with tourists, but even in the off-season, this small village has a more bustling feel than some of the area’s quieter spots.
In addition to enjoying the amenities of Greenport itself, with its range of independent restaurants and shops, as well as gorgeous beaches and quirky museums, local residents are just minutes away from dozens of the acclaimed wineries of the North Fork, which has been called one of America’s best wine regions.
You Love a Slower Pace: Jamestown, Rhode Island
You’ve spent years in a fast-paced and stressful environment, and now you just want to relax. Jamestown, located on Conanicut Island between Newport and mainland Rhode Island, leaves you with no choice but to chill out. This picturesque town is ideal for anyone who loves beaches (there’s a town beach, Mackarel Cove, as well as two coastal state parks), boats (whether you like racing yachts or simply sitting by the docks and watching the sails go by), and water views (you couldn’t avoid them even if you tried).
It also has farms and farmers’ markets; a smattering of local shops and eateries, all best enjoyed at a leisurely pace; and Beavertail and Fort Wetherill State Parks, with hiking trails and scenic views. Many other coastal towns have pretty views and access to the water, but this one is special both for its island location and the way it’s managed to preserve the best aspects of its past while taking advantage of its proximity to larger cities.
Here, on a mile-wide oblong of land in the middle of Narragansett Bay, you can look up at the striking Newport Bridge and suddenly realize you’re not very far from the bustle of civilization—it only feels like you are.
You Love the Outdoors: Portland, Maine
You love outdoor activities, from hiking, skiing, and swimming to fishing and camping, but you don’t want to live too far from the comforts of civilization. Portland, Maine has all the benefits that come with living in a state’s largest city, like charming neighborhoods, a thriving restaurant scene, and an array of seasonal festivals, as well as numerous state parks, cruises, and other opportunities to get out into the wild.
Cyclists can choose between scenic trails along the coast or in the woods near the city or an urban environment—Portland has been called one of the most bikeable cities. If golf, fishing, or paddle-boarding is more your style, there’s plenty of access to these activities, too. And when you’ve seen enough local moose and whales, you can travel to the more extreme wilderness areas in the state’s sparsely-populated north.
You Love the Heat: Miami, Florida
You want to live in a place that embraces that endless summer lifestyle. In Miami, winter lows maybe dip into the 60s. Miamians celebrate their tropical climate on beaches that range from boisterous to child-friendly to unspoiled, in numerous outdoor and waterfront dining spots, and with plentiful golfing and sailing opportunities. Miamians seem to do whatever they can to move everything from art exhibits to yoga classes outside into the sun.
This city is a great choice if you’re looking for the excitement of New York or Boston without the snow. Like those cities, Miami is vast (its metro region is the seventh-largest in the U.S.) and multicultural (Cubans, Haitians, Jews, African Americans, and other groups have helped shaped the city with their rich heritages).
You’re a Day Trip Aficionado: Cincinnati, Ohio
You want to live in a dynamic city, but you also want to take frequent day trips and weekend getaways to nearby places. Cincinnati is just over an hour away by plane from tourist favorites like Chicago and Nashville. Not interested in flying? All-American road-trip routes like the Ohio River Scenic Byway and U.S. 50 (a.k.a. The Loneliest Road) wind right through the city.
Plus, the Queen City has dozens of neighborhoods to explore, each with a unique history and character. Like Italianate architecture and the performing arts? Head to Over-the-Rhine, first settled by German immigrants and now home to the city’s oldest public market. Prefer sporting events, museums, and fine dining? Try Downtown. In this city, you can feel like you’re on vacation without having to leave town.
You’re a Frequent Flyer: St. Louis, Missouri
You want to be close to the airport, but you don’t want to live in a sprawling suburb or bleak industrial zone. The solution: Make your home in a relatively small but vibrant city that’s just a short drive or light-rail trip from the terminal. In addition to airport proximity, St. Louis residents have access to world-class parks and museums.
To name just a few, Forest Park is the nation’s seventh-largest and home to institutions like the Zoo and the stunning Jewel Box floral conservatory. The award-winning City Museum, located downtown, is a one-of-a-kind repurposed industrial playground for all ages. St. Louis ‘s 79 neighborhoods and varied cultural attractions reflect the city’s past and current diversity, from historically Irish Dogtown to proudly Italian The Hill to French-flavored Soulard. And you can’t speak to anyone who lives here for long without noticing their abundant pride in the local sports teams and cuisine.
But when you want to get out of town, you’re as little as 20-30 minutes away from hopping on a flight. And Lambert International Airport isn’t just close, it’s small and user-friendly, so you’ll never have to drag your bag down unending corridors or run for miles to catch a flight.
You’re a Bargain Hunter: Omaha, Nebraska
You want to live in a place that’s affordable, but not one that’s so cheap it lacks amenities or charm. U.S. News & World Report ranks Nebraska as one of the nation’s ten most affordable states thanks to its modestly-priced housing and low cost of living. If you think the Cornhusker State is entirely rural, check out the city of Omaha. Here, home prices are low despite a growing economy and the draw of attractions such as the beautifully restored Old Market entertainment district, extensive parks and trail systems, and lively neighborhoods to explore.
As you’re debating which craft brewery to check out in the Blackstone District, whether to grab a Latin or Lithuanian pastry in South Omaha, or whether to watch a blockbuster at the theater in Askarben Village or an indie film at the cinema in North Downtown, you won’t feel like you’re missing out on anything a pricier city could provide.
You’re an Entrepreneur: Winchester, Virginia
You’re thinking of starting a business, but you want to have a life outside of work. Winchester combines the best of both worlds. On the work side, Virginia is one of the five best states to start a small business. If you’re looking to hire employees, the Old Dominion State is ranked second in labor supply. On the life side, Winchester—located in Northern Virginia’s Shenandoah Valley, about 75 miles from Washington, D.C.—combines the charm of a historic small town with the bustle of an up-and-coming city.
From the dining and entertainment center of Old Town, a charming pedestrian mall lined with historic buildings and businesses, to the Green Circle Trail, from which bikers and pedestrians can access points of interest around the city, this is a place where you can feel engaged with life—even when your days are packed with work.
Of course, you may find that none of these towns match your ideal. But the perfect place for you is out there somewhere. Who knows? You might end up living in and loving some place you haven’t even heard of yet. Just keep an open mind as you do your research. You’ll be sure to find your dream location.
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