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, lakes, rivers, and mountains. And, if you’re on the coast, the Pacific Ocean. 

Key Takeaways:

  • Oregon is known for its abundant natural beauty, outdoor activities, and local food and craft beer scene.
  • Oregon has a relatively high cost of living.
  • The state taxes income from retirement accounts such a 401(k) or an IRA at the full state income tax rates; however, the state has no sales tax.

While the Beaver State is undeniably beautiful, it certainly is not the cheapest place to retire. It has a higher-than-average cost of living, according to, it is not a particularly least tax-friendly state for retirees.

Oregon exempts Social Security retirement benefits from the state income tax but taxes income from retirement accounts such a 401(k) or an IRA at the full state income tax rates. Property taxes are slightly higher than average; however, there is no sales tax.

Housing is also expensive in Oregon. The median home value here is $366,552, versus the $245,193 median home value for the United States as a whole, according to real estate aggregator Zillow. Still, if you are fortunate enough to make the numbers work, here are five of the best places to retire in Oregon.

1. Ashland

Ashland has just over 21,000 residents (according to 2018 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.

2. Astoria

With a population of 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.”

3. Hood River

Hood River ranked high in Thrillist's 2018 list of "America's Best Small Cities to Move to." This city of 7,800 is perhaps best known as a sports mecca: It’s home to some of the best kayaking, kiteboarding, mountain biking, skiing, standup paddleboarding, 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 rainy days, there are art galleries, bookstores, coffee shops, and several museums to keep you busy including the Western Antique Aeroplane & Automobile Museum (volunteer opportunities available).

4. Lincoln City

Lincoln City is a small town of just over 9,000 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.”

5. Florence

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 ocean and lake kayaking and canoeing. 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.

6. 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.

7. Portland

With a population just over 650,000, 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.) Portland has hip food, local craft beers, and a popular craft spirits scene in the city’s famed Distillery Row.

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.