Investor Alert

Where Should I Retire?

Feb. 25, 2021, 9:22 a.m. EST

We want to retire in ‘an area like the Berkshires, but warmer’ — where should we go?

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By Silvia Ascarelli

Dear MarketWatch,

Any ideas for an upscale retirement area with lots of hiking and biking? Great restaurants and culture? Near an airport?  

We are unsure where we want to retire. We live in Northern New Jersey right near New York City. The area has gotten too congested and expensive. Ideally, we would like an area like the Berkshires, but warmer! My husband would love to be on a lake or near mountains. He loves to ski. 

We love outdoor activities, yoga, theater, arts and great food. Doesn’t everyone? We may like a 55+ community so we can socialize.

I know — we are all over the place!



You have so many possibilities. If you want to stay close-ish to New York City, I would do some exploring in the Hudson Valley. It’s a bit warmer than the Berkshires, and closer to the river would be milder, but perhaps it’s still too cold?

Denver could be another great option — close enough to ski slopes, probably warmer and less snowy than you think, certainly thriving. But is it too congested? And the housing market has been hot, so you’d be moving to another pricey spot.

The area around the Oregon Shakespeare Festival, described here , is a possibility, as are other spots in the state suggested here and here .

The MarketWatch “where should I retire” tool can help you match your wish list to metro areas.

I’ve got three options for you in three parts of the country. All will have their pros and cons. As always, spend some time there as if you are a local, not a tourist, to get a feel for what daily life might be like. A bad move is an expensive mistake.

Don’t worry about finding an over-55 community or the yoga classes; they are ubiquitous.

Charlottesville, Virginia

This city, with about 47,000 residents, is home to the University of Virginia. I’m a big fan of college towns because of the amenities they bring, whether lectures, sports or cultural events. Many schools, including UVa, let seniors take classes for free, in this case starting at age 60 .

Charlottesville — and the rest of Albemarle County and its 110,000 residents — is at the edge of the Blue Ridge Mountains and not far from Shenandoah National Park and Skyline Drive . You’ll find plenty of hiking off either Skyline Drive or the Blue Ridge Parkway. In the other direction, you can get to Washington, D.C. in 2 ½ hours, traffic permitting.

Lakes are within a half-hour of Charlottesville. Thomas Jefferson’s Monticello is just outside town, and James Madison’s home, Montpelier, is 25 miles away.

Virginia ranks sixth among the states for the number of wineries at nearly 300, and Charlottesville in the heart of it. With it comes a food scene. The Charlottesville City Market — the Saturday morning farmers market — is consistently voted one of the best farmers markets in the country , as tallied by American Farmland Trust.

You won’t find the most challenging skiing around there. But that’s what airports are for.

Average summer highs reach the upper 80s. In the winter, you’re likely to be in the upper 40s.

Here’s what your housing options could look like , using current listings on Realtor.com, which like MarketWatch, is owned by News Corp.

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