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 its scenic beauty, offering vast expanses of water, sandy beaches and tall evergreen forests. Movie buffs will enjoy touring the spots where more than a dozen famous movies were filmed, including “The Goonies,” “Free Willy,” “Free Willy 2: The Adventure Home,” “The Black Stallion” and “Into the Wild.” 

Hood River

Hood River ranked in the top 10 on Livability’s 2015 “Top 100 Best Small Towns” list. This city of about 7,500 is perhaps best known as a sports mecca: It’s home to some of the best kayaking, kiteboarding, mountain biking, skiing, standup paddle boarding and windsurfing spots in the country, if not the world.

And don’t worry if you’re not the adventurous type. There are plenty of milder outdoor pursuits to enjoy, including hiking, fishing and golfing, as well as visiting the local orchards and vineyards. For those rainy days there are also art galleries, bookstores, coffee shops and several museums to keep you busy, including the Western Antique Aeroplane & Automobile Museum (volunteer opportunities available). 

Lincoln City

Lincoln City is a small town of about 8,500 people located on seven miles of walkable sandy beaches (dubbed “Seven Miles of Smiles”) along the central Oregon coast of the Pacific Ocean. According to its Visitor Information Center, Lincoln City “has the best of Oregon wrapped around a laid-back beach town.”


Florence has a cooler climate and offers a myriad of recreational opportunities. One-third of Florence's population is retired, and the Florence PeaceHealth Peace Harbor Medical Center is the main medical services provider. Florence offers miles of hiking trails and kayak and canoeing options in the ocean and on the two lakes nearby. Fishing choices abound off-shore, off the dock, and on the river. Florence's cost of living is comparable to the state average. The National Sand Dunes Recreation Area is 45 miles south. The Bandon Dunes Golf Resort, a mecca for golfers with five public links courses, is just an hour south of town.

Lake Oswego

Lake Oswego rests primarily in Clackamas County, with small portions extending into Multnomah and Washington counties. Located about eight miles south of Portland and surrounding the 405-acre Oswego Lake, the town was founded in 1847 and incorporated as Oswego in 1910. The city served as the hub of Oregon’s brief iron industry in the late 19th century and is today an affluent suburb of Portland.


With a population approaching 633,000, Portland is the largest city in Oregon and the only big city to make our list. This beautiful metropolis is located in the state’s northwest corner, about 60 miles east of the Pacific Ocean, at the confluence of two rivers: the Columbia and the Willamette. Mt. Hood and Mt. St. Helens dominate the horizon on clear days (on average, there are 144 sunny days a year), and Mt. Adams and Mt. Rainier can also be seen in the distance.

Portland is known not just for its gorgeous scenery and more than 100 nearby hikes with dozens of waterfalls but also for its artsy vibe (it’s home to the Oregon College of Art and Craft), a hip food scene, local craft beers and a growing craft spirits scene in the city’s famed Distillery Row. (For more, see 10 Best Retirement Cities in the U.S.)

The Bottom Line

Whether you dream of spending your retirement surrounded by beaches, dense forests or in a vibrant city, Oregon has something to offer. The cities listed here are just a handful of the places that attract retirees to Oregon. Other spots in the state worth considering include Bandon, Bend, Brookings, Corvallis, Eugene, Florence, Medford (known as a less expensive alternative to Ashland) and Silverton.