Looking To Retire? Here Are 10 Small Towns to Consider

Johnna Kaplan

Not so long ago, the word retirement conjured up an image of moving to Florida, eating dinner at 5:00 p.m., and spending your days doing nothing more exciting than playing the occasional round of golf.

But now, with as many as 10,000 Americans reaching retirement age every day, not to mention advances in health care and technology that allow people to live longer and better, retirement is a chance to start a whole new chapter of your life. It also presents the perfect opportunity to relocate to the sort of town you’ve always thought would be a wonderful place to live, but that work and family obligations made an impractical choice.

The following ten spots may be somewhat off the beaten retirement path, but each offers a unique environment that’s ideal for those who want to spend the next stage of life relaxing as well as enjoying new experiences. And only one of them is in Florida.

Portsmouth, New Hampshire

Though it’s technically a city, Portsmouth’s New England charm blends the best of small-town life with the vibrancy of a cultural center. To put it another way, this historic seaport has all the charm of Boston, without the traffic and sky-high rents. It’s hard not to love Portsmouth’s bookstores, independent shops, museums, and proximity to beaches and other regional attractions. Retired people will also be grateful for New Hampshire’s low cost of living, relative to other New England states, and the absence of sales tax.

Niantic, Connecticut

An array of beaches, boardwalks, restaurants, shops, and art venues are among the benefits of living in this coastal New England village. From Niantic, it’s easy to visit New York, New Haven, Providence, or Boston by train, but there are plenty of reasons to stay home, given the casual coastal atmosphere and the range of activities available here. Fans of sailboats, sunbathing, and seafood will love this little town, and retirees looking to invest in property will appreciate the fact that real estate here is relatively affordable compared to much of the Connecticut coast.

Lancaster, Pennsylvania

This small yet diverse city is surrounded by some of the most fertile farmland in America, making it the best of both worlds for anyone who likes having dining and entertainment options as well as a sense of calm and open space.

Walkable and historic, Lancaster offers art galleries, coffee shops, and a sense of community. A well-known gem is the Lancaster Central Market, the oldest continuously operated farmers’ market in the country, where shoppers can buy everything from flowers to baked goods to specialty foods as well as meat and produce supplied by local Amish farmers.

If you currently live in a major East Coast city, Lancaster is far enough to feel like a big change, but close enough that trips back to your former home are short and easy.

Fernandina Beach, Florida

A short distance from the center of Jacksonville, Fernandina Beach is a small city on Florida’s scenic Amelia Island, a tranquil escape with a tumultuous past. (It’s known as the “Isle of 8 Flags” for its numerous changes in government.) From Fernandina Beach’s vintage postcard-like downtown, to the area’s luxury resorts and spas and stunning state parks, locals and visitors can always find something to do—or a beautiful setting to do nothing.

All the reasons retirees flock to Florida (lower taxes, multiple golf courses, warm weather, etc.) also apply to Fernandina Beach, but this town is hardly a retirement community. Its events and attractions, from the book and music festivals to the sailing and fishing charters, will appeal to people of all ages and activity levels.

Madison, Indiana

This slow-paced Midwestern town speeds up every summer when hydroplane boats take to the Ohio River for the Madison Regatta. Other types of events draw visitors to Madison throughout the year, as does its architecture: Madison’s downtown business district has been lovingly preserved, creating one of the largest National Historic Landmark Districts in America.

Madison is a nice base for exploring the parks, scenic byways, trails, and wineries nearby, but it has plenty of attractions right in town too, including a walkable downtown, a riverfront park, restaurants, house museums, and antique stores. Madison also has a special volunteer program geared towards matching retirees with local nonprofits.

Natchez, Mississippi

It might have a population of over 15,000, but Natchez feels like a much smaller community. Perhaps it’s the leisurely pace of this Southern city, or the ease of walking around its picturesque streets. Natchez is suffused with history, from the antebellum homes that attract visitors to the ghost that is said to frighten diners in a popular local restaurant.

Anyone seeking to avoid the cold and embrace the romance of the Mississippi River will enjoy Natchez. And since 1997, Mississippi has rated Natchez as a Certified Retirement City, meaning it possesses many of the qualities most retired people look for in a community, like low taxes, quality health services, and a significant number of other older adults living in the area.

St. Charles, Missouri

Just 25 minutes from the vibrant, culture-packed neighborhoods of St. Louis and a short road trip away from Missouri’s serene wine country, St. Charles mixes classic Midwestern appeal with its own French- and Spanish-influenced flavor. This small Missouri River city, with its brick streets and eye-catching architecture, manages to feel calm yet bustling at the same time.

Visitors and residents alike enjoy checking out Main Street’s restaurants and stores, learning about the area’s rich history, and biking or hiking America’s longest rails-to-trails project, the Katy Trail. Retirees can take advantage of Missouri’s relatively low cost of living; it is also one of the cheapest states for long-term care.

Helena, Montana

If you plan on devoting your retirement to an active life in the great outdoors, this small town (well, it feels like one, though it’s actually the capital city of Montana) is a perfectly picturesque starting point for mountain adventures. From its beginnings as a gold rush-era mining camp, Helena has grown into a fully developed showcase of the region’s art, architecture, entertainment, and cuisine.

Situated just east of the Continental Divide, it’s surrounded by some of the most dramatic vistas in the country, laced with numerous biking and hiking trails, national parks, and ski areas for nature lovers and active residents to explore. Helena was founded by four miners who happened to strike gold in a spot they named “Last Chance Gulch,” and if you see retirement as a chance to take a risk and reinvent yourself, it’s hard to beat this sparsely populated state.

San Luis Obispo, California

Situated on California’s Central Coast between the mountains and the ocean, this small, lively city has something for everyone. It’s part college town (the college being California Polytechnic State University), part living history museum (the 1772 Mission San Luis Obispo do Tolosa, out of which the city grew, is still a functioning parish church), and part cultural hub (there are numerous theaters and museums).

Stay close to home to enjoy the second-largest farmers market in the western United States, or get away on Amtrak’s scenic Coast Starlight train to L.A., San Francisco, Portland, and Seattle. Miles of trails and other outdoor activities abound here, and if you’re counting on retirement to free you from decades of shoveling snow, you’ll be glad to know it’s sunny about 300 days of the year in San Luis Obispo and it’s not uncommon for temperatures to reach 80 degrees in February.

Astoria, Oregon

This little city on the Columbia River was the first permanent American settlement on the west coast. Today, it’s known to tourists for its downtown shops, quaint riverfront trolley, and the intricately painted and difficult-to-climb Astoria Column.

When the cruise ships that frequent the Port of Astoria leave, the city’s authentically quirky Pacific Northwest atmosphere is revealed. It’s a pleasure to wander around Astoria and the surrounding coastal region – even in the rain. For those who plan to live here when their driving days are over, extensive bus service and a local commitment to ride-sharing and helping people access public transit means it’s easy to get around the area—and beyond—without a car.

Even if you don’t spot your ideal retirement location in one of the towns above, hopefully this list will inspire you to think outside the box when it comes to relocation. Once you embrace the fact that your retirement can look like anything you choose, your options will begin to seem practically endless.

2 Responses to "Looking To Retire? Here Are 10 Small Towns to Consider"

  • David Smith | November 7, 2018 at 3:44 pm

    Your article on retirement towns was interesting. I live in Old Saybrook Ct and would include it in your list. It is shoreline with 2 wonderful beaches, a great downtown and a pretty good mix of wealth and moderate wealth. Taxes are one of the lowest of shoreline towns.

  • Lorette L. Belval | February 24, 2018 at 3:41 pm

    Enjoyed your info on all of these retirement areas. Please continue with article such as these and even other subjects of interest for retirees. Thank you

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