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Where Should I Retire?

Dec. 29, 2020, 4:36 p.m. EST

‘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

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By Silvia Ascarelli

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The website Livability says this city of 100,000 in central Oregon “ provides easy access to all the outdoor adventures you could ask for .”

Quirky fact: there’s a dormant volcano in town called Pilot Butte that offers great views of the Cascade mountains. But don’t miss the Newberry National Volcanic Monument 20 minutes outside of town and the hot springs at Paulina Lake a bit further away. And take some time for the 66-mile Cascade Lakes Scenic Byway .

Average summer highs are in the low 80s, and humidity is low. 

You won’t find many places more walkable; Walkscore calls Bend a “ walker’s paradise ” and gives it 91 points out of 100.

Is this the place for you?

You will get snow — an average of about 7 inches to 8 inches in both December and January. But even then, average daytime highs are in the low 40s, and there’s not much rain. 

Unlike many people, you have the housing budget for Bend. (Yes, it’s more expensive than Portland , according to Sperling’s Best Places.)

Here’s what homes are on the market now using listings from Realtor.com (which, like MarketWatch, is owned by News Corp.)

Here’s a laid-back mountain town where housing costs, while well above the national average, are cheaper than in Bend . Livability includes Flagstaff in its latest rankings of 100 best smaller and midsize cities to live in , citing an “impressive quality of life” and “tons of arts and entertainment options.” Its 75,000 residents value recreation and being outside. And with seven national parks sites within 80 miles, why not?

Of those, the Grand Canyon is furthest away, but just outside the city is Walnut Canyon National Monument . Head south, toward pricier Sedona, and drive through Oak Creek Canyon Scenic Drive .

Yes, there are four seasons, and I admit I was worried about the amount of snow — an average of 108 inches in downtown Flagstaff, according to the local tourism office. Yikes! Locals insist that while you can get a big snowstorm, it’s not like a storm that hits the Midwest or the East Coast. Here, at an elevation of 7,000 feet, it will be followed by sunshine and highs around 50, so snow won’t stick around for long. (Some newer homes even have heated driveways so you don’t have to shovel — or you could pay someone to do it.) 

Of course, you can use a pending snowstorm to spend some time in the Phoenix area a little over 2 hours away. And skiers will head to the Arizona Snowbowl 15 miles up the road.

Still, this is a reason to spend some time experiencing Flagstaff in the winter before making a decision.

Otherwise the weather is beautiful from April through October. July highs average 82 degrees. There’s no humidity –a relief after Houston.

Unlike so much of Arizona, Flagstaff isn’t dominated by retirees, even as snowbirds. The Census Bureau says just 8.3% of the population here is 65 or older, half the national rate. Chalk some of that up to Northern Arizona University and its 20,000-plus students. As I’ve written before, I’m a fan of college towns because of the sports and cultural events they offer residents of all ages.

Walkability here is so-so. Interstate 40 and railroad tracks cut through town, so if you want to walk to local restaurants, you may want to live near downtown. On the other hand, you probably won’t drive more than 10 minutes to get anywhere in town. For more casual walking, enjoy the 56-mile Flagstaff Urban Trail System (FUTS) .

Intrigued? Here’s what’s on the market , again using listings on Realtor.com.

Your interest in Cascais has me thinking about a place on the water, but your aversion to Houston-style humidity has me skipping southern beach towns. Go too far north, and the winters rule them out (unless you want to turn winter into prime travel time). I’m also thinking of a place with enough to do year-round, so too rural or seasonal a spot could be a bad fit.

Annapolis, the capital of Maryland and on the Chesapeake Bay, could be a sweet spot. You’d have a somewhat walkable community of 39,000 (in a county of 580,000 people), paddleboarding and other water activities in a city that calls itself the sailing capital of the United States — plus the proximity to Maryland’s Eastern Shore and its beaches. Explore the area crab shacks until you get your fill of seafood. And then explore the rest of the local foodie scene .

While Annapolis has its share of theater, music and other cultural events — and check out the First Sundays Arts Festival — you’d also have easy access to big-city amenities in Washington, D.C. and Baltimore.

Average winter daytime highs are in the 40s, and average summer highs are in the upper 80s, meaning you’ll have more of that hot summer feeling than in either Bend or Flagstaff. Annapolis does get a bit of snow, mostly in January — an average of nearly 4 inches then.

Granted, this city is another pricey option, but you have the housing budget to handle it. Here’s what the local housing market looks like now .

A city alternative: Philadelphia , one of America’s most walkable cities and an hour to the Jersey Shore beaches.

Readers, where do you think L & K should retire? Leave your suggestions in the comments section.

Also read: I want year-round outdoor living — dry summers and no snow — on $4,000 a month. Where should I retire?

And: I’ll retire with a military pension and want to move to a bicycle-friendly, beer-loving place — so where should I go?

Plus: We love to ski but are struggling even with a $1 million house budget — what’s an affordable ski town where we can retire?

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