Oregon is not on the top of everyone’s list of places to retire; however, maybe it should. Oregon has picturesque beaches, mountains, and rivers, plus it is abundant in art and culture. As this gem of a state has grown in popularity, it has also expanded its retirement community and there are now many perfect places to retire in Oregon.
And though Oregon isn’t the most tax-friendly state, it is far from the worst. Oregon does have a retirement tax but does not have a social security tax. Also, pension income, both public and private, are only partially taxed. But the best tax benefit Oregon offers is their lack of sales tax.
Another benefit of retiring in Oregon is that it is a healthy state for active retirees. With a multitude of outdoor activities that can be enjoyed year-round, including over 300 miles of public beaches, retirees never need to worry that they will become sedentary.
In addition to being active, Oregon is also a mecca for fresh produce. It is full of orchards and farms, making finding fresh fruits and vegetables accessible and convenient.
Plus, depending on where you live, getting around without a vehicle can be quite easy, especially in Portland. Portland has been named, on several occasions, one of the most bicycle-friendly cities in the country, making the expense of vehicle ownership obsolete.
In addition to its scenic outdoors, Oregon is one of the top wine-producing states in the country, making it the ideal place for the wine-loving retirees. Oregon is home to over 300 wineries, several of which are open to the public, which is perfect for an afternoon outing.
And for the beer connoisseurs, Oregon is also a fount of breweries boasting more than 200 craft breweries. Plus, Oregon also hosts an annual Brewers Festival every July in at Tom McCall Waterfront Park in Portland.
If you need more convincing that Oregon is a great place to retire, the state’s crime rate is lower than the national average, giving you peace of mind that is worth its weight in gold.
Of the many different cities in Oregon, we have chosen a variety of options. We included large metropolitan areas such as Portland, with a population higher than 400,000, along with smaller towns with less than 10,000 residents.
Though the cities’ sizes may vary, the one thing they all have in common is that they all have a wide variety of activities to keep any retiree happy and boredom free.
Places to Retire in Oregon
- Portland
- Lake Oswego
- Ashland
- Astoria
- Hood River
Portland
- Percent of Senior Population: 11.9%
- Overall Population: 664,103
Portland is the largest city in Oregon and is continuously growing. It is a city that has the best of both worlds, urban culture and convenience, combined with the great outdoors. Portland is home to more than 200 parks, including a Forest Park spanning 5,000+ acres.
Plus, Portland, conveniently located with access to several rivers and mountains, gives active retirees several outdoor outlets to keep them healthy. And for the golfers, there is an abundance of beautifully groomed courses throughout the Portland area, which are open most of the year.
Additionally, as mentioned earlier, Portland is exceedingly bicycle friendly with 270 miles of bike trails and specially marked, with non-skid paint, bike lanes throughout the city. And if you aren’t a cyclist but don’t feel like driving, Portland offers a wide range of public transit options like bus, light rail, and commuter rail options.
As for housing in Portland, there are several choices from well established single-family homes to new construction senior communities. Also, there are a variety of different neighborhoods within the city limits, such as the warehouse district abundant in restaurants, shops, and galleries or more suburban areas with a bit more living-space or the waterfront for houseboats.
Unfortunately, one of the drawbacks of living in a big city is the increase in the crime rate. But on the flip side, large cities also offer a greater number of choices for medical care. And Portland has its residents covered when it comes to providing an ample number of medical centers.
They are even home to the OHSU (Oregon Health and Science University) hospitals and clinics. And according to U.S. News, the OHSU is the number one ranked hospital in all of Oregon.
Lake Oswego
- Percent of Senior Population: 18.6%
- Overall Population: 40,726
Just south of Portland is Lake Oswego, which spans 405 acres. This beautifully magnificent city easily attracts retirees to its lakefront.
Active retirees, especially enjoy Lake Oswego for its many parks. There are over three hundred acres worth of parks scattered throughout the city, allowing residents to hike, bike, jog, bird watch, and fish. Some of the more popular city parks in the area are:
- Bryant Woods-Canal Acres-River Run
- Cooks Butte-Stevens Meadows
- Springbrook Park
- Iron Mountain Park
Also, the park and rec department offers local golf courses, indoor tennis, and a water sports center, so there are a variety of physical activity options available for the residents of Lake Oswego.
In addition to Lake Oswego’s many outdoor activities, the city is very rich in art and culture. Every year Lake Oswego hosts a three-day event, the Festival of Arts. This festival is a time-honored tradition dating back to 1961 put on by the Lakewood Center for the Arts and Lakewood Theatre Company. The festival offers:
- Visual Arts
- Live Performances
- Artist Demonstrations
And, the city offers several different senior services, including a senior center, van services, and home-care. Plus, being just 12 miles from Portland residents have access to all of the urban amenities such as:
- Restaurants
- Theater
- OHSU Hospitals and Clinics
Though in truth, Lake Oswego does offer an array of fine eateries and shopping all at a more laid back pace than Portland.
Ashland
- Percent of Senior Population: 21.3%
- Overall Population: 21,621
Ashland, surrounded by mountains and hills, is located in the southern region of Oregon just 16 miles north of the California border. It is a town best known for its art, culture, and outdoor activities.
Ashland is a town steeped in culture and arts, including theater. Every year since 1935, they have hosted the Tony Award-winning Oregon Shakespeare Festival. This world-famous festival attracts more than 400,000 tourists every year.
In addition to the arts, Ashland is the perfect place for retirees looking for outdoor adventure. It is easy to find breathtakingly beautiful places to hike, camp, ski, canoe, or even go whitewater rafting. Plus, there are several bikeways for cyclists to explore the Ashland foothills. And because there is both river and lake access, it is the ideal location for those who love to fish.
For the wine lovers, Ashland is just north of some of California’s most celebrated wine country, easily accessible and a great way to spend an afternoon checking out the vineyards.
Ashland’s small-town feel fits well with the Victorian style housing, though if that is not what you are looking for, there are plenty of modern-looking homes as well. The town is a mix of both new and old architectural styles.
Ashland is the perfect place for retirees who are looking to escape the big cities for a quieter, more relaxed lifestyle.
Astoria
- Percent of Senior Population: 20.4%
- Overall Population: 10,036
The smaller town of Astoria has a long history as the oldest settlement west of the Rockies, established in 1811. It is located in the northwest region Oregon along the Columbia River just a few miles from the Pacific Ocean.
For retirees looking for edgier outdoor adventure, Astoria is the town for you. This small town is an outdoor adventurers dream come true. It, of course, offers the standard hiking and biking trails, fishing, and camping. But Astoria also offers parasailing, paddle boarding, and scuba adventures as well.
In addition to the abundant outdoor activities, Astoria is also features:
- Columbia River Maritime Museum
- Liberty Theater
- The Astoria Festival of Music
Plus, because Astoria’s main economy stream comes from tourism, the town features several outstanding restaurants and boutiques.
According to Zillow, the median housing prices in Astoria are around $274K, as of mid-2019. Many of the homes feature a Victorian fashion architecture that fits well with the remodeled old-style downtown look.
Also, another benefit to retiring to Astoria is the low crime rate. Though it is a tourist town, which can attract a certain amount of crime, Astoria has done well to maintain a safe environment for its residents.
And though Astoria is small, it still is home to the Columbia Memorial Hospital and has three medical centers per 1,000 residents.
Hood River
- Percent of Senior Population: 12.9%
- Overall Population: 8,096
Hood River, the smallest town on our list, is located in the Columbia River Gorge, a beautifully scenic area with 4,000-foot cliffs perfect for windsurfing. Tucked in along the river, Hood River offers a lot for the outdoor adventurers including a multitude of water sports such as:
- Fishing
- Windsurfing
- Paddle boarding
- Kayaking
- Jet Skiing
- Sailing
In addition to the abundance of outdoor activities, Hood River is also home to several orchards and vineyards. The town also hosts a couple of different festivals in the spring and fall, Blossom Fest and Harvest Fest. Plus, the downtown area is full of charming boutiques and delicious restaurants.
Portland is only an hour’s drive from Hood River, making it accessible for a day or night out in the big city. Plus, if you are looking for a larger hospital, OHSU is still a reasonable drive.
But, don’t worry, Portland is still far enough that the hustle and bustle of the urban area won’t impact small-town life.
One of the drawbacks of living in Hood River is that the cost of housing is a bit spendier than the national average, coming in around $480K, according to Zillow. However, the good news is that Hood River’s crime rate is lower than the national average.
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