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

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

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.

The University of Virginia campus in Charlottesville.

Getty Images

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.

Two Virginia alternatives: Harrisonburg, suggested here, and Roanoke, suggested here.

The Coeur d’Alene area is full of lakes.


Coeur d’Alene, Idaho

You’ll find plenty of natural beauty, particularly lakes (55!), in the area around this northern Idaho city of 52,000 people. Coeur d’Alene is in the Rocky Mountains, surrounded by forest, and the skiing is just 40 minutes to the east at Silver Mountain Resort or 75 minutes north at Schweitzer Mountain

This is a resort town, so you’ll find that upscale vibe. Downtown is lively and includes local theater. But if you can’t find what you’re looking for (or want to catch a touring Broadway show), Spokane and its 217,000 residents are just 45 minutes away. That’s where you’ll find the airport too.

You can get to Spokane by bike: The 24-mile North Idaho Centennial Trail connects at the state line to the 37.5-mile Spokane River Centennial State Park Trail. In the other direction is the Trail of the Coeur d’Alenes and the Route of the Hiawatha (with its 1.6-mile tunnel). 

Average temperatures will be warmer than the Berkshires, both in the summer and winter, although winters are the coldest of my three suggestions. Be prepared for lots of snow.

Many retirees have discovered this area; the share of residents over 65 in Kootenai County is above the national average. The downside is that Coeur d’Alene was already a “very hot” housing market before the coronavirus pandemic hit, according to Realtor.com, and prices are above the national average. 

Click here to see what’s on the market now, again using Realtor.com listings.

Another Idaho option: Boise, suggested here.

The Crystal Bridges Museum in Bentonville, Ark.

Courtesy Visit Bentonville

Bentonville, Arkansas

This is my warmest version of the Berkshires, given that it’s in the Ozarks, a mountainous region in southern Missouri and northern Arkansas. (These are not the Rockies — the highest elevation is just over 2,500 feet, or 300 feet lower than the highest point in the Berkshires.) 

Bentonville is also the home of the Walton family, so you won’t escape the influence of Walmart. I mean that in a good way.

The Crystal Bridges Museum of American Art, with its Andy Warhols, Keith Harings and other top names in American art, and the Momentary, a contemporary art space that opened in an old Velveeta factory just before the coronavirus pandemic hit? They exist thanks to Walmart money. Both are free.

The 500 miles of purpose-built mountain bike trails across Northwest Arkansas (and the three additional miles being built every week) — that’s because of Walmart, too. Outside magazine calls Bentonville “Disneyland for mountain bikers”. Two of the multiday loops in Adventure Cycling’s Arkansas High Country Route start in Bentonville.

Then there are the James Beard-nominated chefs, patronized by those who move to the area because of Walmart or visit because of Crystal Bridges or the mountain biking. 

Bentonville has about 60,000 residents; about 279,000 live in Benton County. Add in Washington County (home to Fayetteville), and the area has more than half a million residents. More than half the people living in northwest Arkansas are not from the state, so the feel here is somewhat different from the rest of the state, even if the politicians remain conservative.

For lake living, look around Beaver Lake (actually a reservoir) in nearby Rogers or the many lakes in Bella Vista, just north of Bentonville. The University of Arkansas is 25 miles south in Fayetteville; those 60 and older can take classes for free

Compared with Charlottesville and Coeur d’Alene, Bentonville has the lowest share of people 65 and older; if you prefer a more retiree-heavy spot, look at Bella Vista.

And the weather? It gets below freezing at night in the winter and you could get several inches of snow. But average highs are in the upper 40s, if not the lower 50s. Summer highs average close to 90.

Here’s what the housing market looks like, again using listings on Realtor.com.

More MarketWatch’s ‘where should I retire’ columns

‘Work and a few vacations each year is all we’ve done for the past 34 years’ — This couple has $2.6 million and no idea where to retire

I’m looking to retire in a warm place that has a ‘socially liberal mind-set’ and lots of live music — and I’m a die-hard skier. Where should I go? 

We want to retire somewhere in North Carolina or South Carolina on $3,400 a month in Social Security — where should we go?

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