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Where Should I Retire?

Sept. 25, 2021, 10:15 a.m. EDT

We want to retire in the Carolinas or Virginias in a walkable town neither too large nor too small — where should we go?

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By Silvia Ascarelli

Hello,

We are looking to retire in a few years and are looking through the Carolinas and Virginias. We would like a town that isn’t too large or too small. It would be nice if there were some cultural facilities such as a theater and museum and if it were walkable to restaurants and stores. <EMPHASIS>We like the Appalachian Trail.</EMPHASIS> I also like homes with character.

We went to Harpers Ferry and although very nice, not quite what we were looking for. We are going to Asheville in October.  

Any suggestions are welcome.

Eileen

Eileen,

As you’ve discovered, a place can look good on paper but still not be quite what you want. And when a place does look right, I hope you’ll spend some time to make sure by pretending this is your new day-to-day, rather than experiencing it as a tourist.

Only you know what not too big and not too small means — and that’s quite a difference between Harpers Ferry and Asheville, both in size and budget. I’ll be curious about your reaction to Asheville, but while there, look at both Hendersonville and Brevard , which have been suggested in MarketWatch’s “Where Should I Retire” series

I’ve also previously spotlighted other communities that might appeal: Harrisonburg , Roanoke , Blacksburg and Lexington in Virginia. The AT doesn’t go through South Carolina, but I’d flag Greenville . If you’ll extend your search to Tennessee, look around Knoxville (the city might be too big for you) or Cookeville .

The MarketWatch “ Where Should I Retire ” tool may help you discover other places.

I’m listing a few other options below. Remember that walkability to restaurants and stores is more about the neighborhood than the town or city as a whole. Given that you also want a house with character, focus on older neighborhoods. 

Finally, you make no mention of your retirement budget and how much you can spend buying and fixing up that house. If you haven’t already, take some time to assess your finances. Be conservative; the stock market won’t always be your friend.

Staunton, Virginia

Here’s a smaller, walkable town in the Shenandoah Valley within an hour of mountains. Staunton, home to 25,000 residents, has a number of historical districts (watch for free walking tours ) and is home to a small, private liberal arts school in Mary Baldwin University

The city’s theater hub is the American Shakespeare Center and its Blackfriars Playhouse, the world’s only re-creation of Shakespeare’s indoor theater. History buffs might appreciate the Woodrow Wilson Presidential Library and Museum . You’ll also find live music festivals all summer long.

When you want something bigger, go 40 miles east to Charlottesville ( suggested here ) and the University of Virginia campus. If you’re thinking about the beach, the Atlantic Ocean is about 3 hours away.

Winter highs average in the 40s, though you will have snow. Average summer highs reach the mid-80s.

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