If you’re ever considered retiring to a new part of the country, take a long vacation there first. You’ll relax and see the sights but also check out neighborhoods and homes, talk to locals, maybe even visit health-care amenities. Compared with a “standard” vacation, you’ll come away with a much better idea of whether this is a place you might like to retire. Here’s how to take this sort of trip to the beautiful town of Bend, Oregon…

A popular bumper sticker spotted around Bend, Oregon, reads, “Your vacation is your life.” That pretty much sums up the appeal of this attractive and friendly town in central Oregon’s high desert country. The Cascade mountains lie just to the west, so outdoor adventures are easy to find, and there are plenty of culinary and other indoor pleasures, too.

To be sure, it’s not the most affordable place in the US to retire, and transportation is tricky if you don’t have a car. Nor does it offer the ethnic diversity that bigger cities do. But there are plenty of reasons why this town, which includes plenty of young people, is home to roughly 15,000 retirees out of about 95,000 residents.

Here’s what you need to know if you want to enjoy a pleasant week or two—and then possibly plan for a new life—in Bend, Oregon…

Natural Pleasures

The outdoors is the main draw, and you don’t have to leave town to enjoy more than 70 parks, 65 miles of recreational trails, several golf courses and the shores of the Deschutes River as it cuts a swath through downtown. You can even ramble up Pilot Butte, a nearly 500-foot-tall volcano (don’t worry, it’s extinct). Within an hour’s drive are dozens more golf courses, ski slopes on Mt. Bachelor, pristine lakes and white-water streams popular with kayakers and trout anglers.

Bend is not a cloudy, dreary place like many people might assume because it’s in the Pacific Northwest—in fact, it enjoys an average of 158 sunny days per year with an additional 105 mostly sunny days. The weather makes it easy to get outdoors. While Portland, 165 miles to the northwest, averages about 37 inches of rain a year, Bend gets only 12. It does get about 24 inches of snow a year, which makes it attractive to skiers but not as snowy as say, Denver, Colorado, which averages about 60 inches. High temps in the summer average 82°F. In the winter, the highs average 48°F and the low temperature averages 24°F.

Indoor types won’t feel out of place in Bend, either. Beer lovers will appreciate the 24 craft breweries, and Bend has plenty of good restaurants for a city its size, many stressing local farm-to-table sourcing and sustainability. Would-be residents with four-legged companions might be pleased to know that Bend ranks as the most dog-friendly city in the US according to Dogster (formerly Dog Fancy) magazine because of its temperate weather, off-leash dog parks and many miles of accessible dog-friendly trails. (There also are dozens of restaurants where you can dine with your pooch alongside.)

Retirement Essentials

Retirees need a little more than hikes and beers, of course, so here’s the skinny on health care, housing and more…

Housing. Bend’s housing market is said to rise and fall as dramatically as the surrounding Cascade mountains. After a boom in the early 2000s, prices plummeted in the Great Recession—but are soaring again. Median home value is now $347,000, according to City-Data, a national website that relies on official government data. That’s high above the national median value of $255,000 but well below the cost of homes in many of the larger metropolitan areas where many retirees live before they move. Median rents are $1,200. The area has several retirement communities, as well, including The Falls at Eagle Crest (a 55-plus community) and Sunriver, a vacation resort that offers year-round homes for sale or rent.

Culture. The joke is that diversity in Bend, where 86% of the population is white, means having a different-colored Subaru. But the arts community does bring in cultural diversity, at least. There are vibrant theatrical, fine arts and crafts communities, and kids get exposed to theater early through the nonprofit Bend Theatre for Young People. The city hosts outdoor summertime concerts in parks, and at the Les Schwab Amphitheater and the downtown Tower Theater, several theater groups (such as Cascades Theatrical Company) stage year-round programs of drama, music and other events. A creative hub is The Workhouse, providing studio space, a shop and events for local artists and craftspeople.

Health Care. St. Charles Medical Center in Bend is the largest hospital in central Oregon, and US News & World Report ranked it as one of the top 10 hospitals in the state. Residents of Bend typically go to Portland for specialized care if it’s unavailable in Bend.

Transportation. Bend is a decidedly car-oriented town, though Cascades East Transit operates limited bus routes around town and some shuttles to Mt. Bachelor and other popular recreation spots. Several airlines operate out of the airport in Redmond, 17 miles north, and they provide direct flights to and from Portland, as well as Los Angeles, San Francisco, Seattle and a few other cities.

Planning Your Tryout Trip

Bend is a popular vacation destination in summer as well as winter. But fall actually is a great time to visit if one of your goals is to check out the area for possible retirement. Fall is when the summertime crowds have headed back to school and jobs…and mountain snowfalls have not yet closed off many of the higher-elevation attractions. If you can, go in September or October, as these snowfalls can come early. You may want to plan for at least a few weeks to vacation and check out the area for possible retirement.

Top in-town experiences include a visit to the Old Mill District, where shops, restaurants and breweries occupy old lumber mill sites on the shores of the Deschutes River, combined with a stroll along the riverbanks in downtown Drake Park. Exhibits at the High Desert Museum provide a fascinating look at the area’s unique natural environment and indigenous peoples.

Head out of town in any direction for a multitude of outdoor attractions. Scenic stops include the lunarlike landscapes of Newberry National Volcanic Monument…the easily accessible wilderness of the Deschutes National Forest…the volcano-rich Oregon Badlands, a US Wilderness Area…the lovely pine-scented Metolius River region…and popular spots along the Cascade Lakes Scenic Byway. Stop at the Bend Visitor Center, at 750 NW Lava Road, for info on what to see and do and for some advice (and perspective) on retirement options.

For dining, check out McKay Cottage Restaurant for amazing breakfasts…tiny Ariana for a French/Italian/Spanish-inspired dishes…Jackson’s Corner for farm-to-table dining with homemade pasta and craft beers…Barrio for tacos and paella…and Zydeco Kitchen & Cocktails for Cajun and Creole dishes, Northwest style. But don’t neglect Bend classics Pilot Butte Drive-In (famous for its burgers) and Pine Tavern, a throwback to Bend’s 1930s frontier-town days where a pine tree grows through the paneled dining room. The prime rib is fantastic, and its big windows overlook the beautiful Deschutes River. Tip: The most romantic table in the house, with the best view, is called “Bob”…locals ask for it by name when making a reservation.

Bend Cottages rents out a dozen or so character-filled homes around the town center (from $109 nightly for two, with discounts for weekly and monthly stays). The Riverside Inn & Suites features fireplace-equipped units facing gardens along the banks of the Deschutes River (off-season rates for a double begin at $95). For a more upscale experience, splurge at the trendy, eco-friendly Oxford Hotel (doubles typically more than $300).

Since you are checking out Bend as a possible future home, be sure to explore the residential areas beyond downtown and the commercial district centered around 3rd Street. The area to the west is more timbered, more expensive and most desired. Areas to the east, with more sagebrush, are lovely, too, and more affordable. Sunriver, the retirement resort, is to the south. If you head north, toward Redmond (about 17 miles away), you’ll find more affordable housing, too. (Redmond itself is a popular retirement destination, so you might want to check that out, too.)

Bend attracts a wide diversity of retirees. It’s not ideal for the true urban dweller who revels in the bustle, excitement and essentially limitless activities of a big city. But it’s a great place for people who are seeking many outdoor opportunities…combined with enough art, music and other cultural events to stay engaged and entertained…and complemented with a surprisingly vibrant local dining scene.

Interested in other retirement destinations worth checking out on vacation? See Vacation Where You Might Retire: San Miguel de Allende, Mexico.

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