The best places to retire in Oregon all have something in common: abundant natural beauty. No matter where you retire in Oregon or how you plan to spend your time – be it playing a round of golf, hiking, kiteboarding or enjoying the local food or craft beer scene – you’ll be surrounded by a natural backdrop of dense forests, lowlands and mountains, plus a host of lakes, rivers, streams and, if you’re on the coast, the Pacific Ocean.

While the Beaver State is undeniably beautiful, it certainly isn’t the cheapest place to retire. It has a higher-than-average cost of living, and it’s one of the least tax-friendly states for retirees, according to a 2016 report from Kiplinger (there is no sales tax, however). Housing is expensive, too: The median home value here is $287,500, versus the $189,400 median home value for the U.S. as a whole, according to real estate aggregator Zillow. Still, if you’re fortunate enough to make the numbers work, here are five of the best places to retire in Oregon. (For more, see States with the Biggest (and Smallest) Tax Burden.)


Ashland has just under 21,000 residents (according to 2015 U.S. Census estimates) and is located 16 miles north of the California border, in the southwest corner of the state. The city has hosted the Tony Award–winning Oregon Shakespeare Festival every year since 1935 and is considered one of the country’s best small art towns.

In addition to being a cultural hot spot, Ashland offers a mild climate, a small-town atmosphere and plenty of opportunities to play outside, whether you want to bike, hike, ski, snowboard or go whitewater rafting.


With a population under 10,000, Astoria was named one of Smithsonian Magazine’s “Best Small Towns to Visit” in 2013. It’s been called “Little San Francisco” because of its steep streets, Victorian homes and bayside setting. Located near the mouth of the Columbia River, Astoria is just a few miles from the Pacific Ocean in Oregon’s extreme northwest corner, where year-round mild temperatures are the norm.

The city is known for…