Feeling the itch to settle down after a lifetime of hard work? Oregon offers a world of possibilities with its diverse landscapes and lifestyle choices. From the majestic peaks of the Cascade Range to the tranquil waters of the Pacific coastline, there’s a retirement haven waiting just for you.
Seeking the best place to live in Oregon for retirement, you may find the selection process a bit overwhelming. From cities like Portland to tranquil locales like Coos Bay and Cottage Grove, there are numerous options for every preference.
Why Oregon Is Ideal for Retirement
Oregon, fondly known as the Beaver State, is a popular destination for retirees. The state offers many attractions for those seeking a peaceful yet active retirement. The natural beauty of places like Coos Bay and the quiet charm of Cottage Grove, along with the cultural vibrancy of cities like La Grande, make Oregon an appealing choice.
In particular, two locations that stand out are Lake Oswego and Cottage Grove. Lake Oswego, known for its upscale living and close-knit community, offers a wealth of recreational activities and amenities. Imagine spending your golden years sailing on the serene lake or exploring the city’s charming boutiques and gourmet restaurants. The city also boasts a low crime rate, adding a level of comfort to your retirement.
Whether you’re a nature lover, an arts enthusiast, or a fan of outdoor activities, Oregon has something to offer. The stunning beauty of Coos Bay is a treat for nature lovers, while Cottage Grove’s peaceful environment is perfect for those seeking tranquility. In contrast, La Grande offers a mix of cultural and recreational activities for a lively retirement.

Highlighting the 10 Best Cities to Retire in Oregon
1. Hood River
If you are an adventurous retiree, Hood River is one of the best places to retire in Oregon. This charming city in Hood River County, nestled on the river of the same name, is a gem. The city’s proximity to Mount Hood and the Columbia River Gorge provides plenty of opportunities for outdoor recreation. The city is blessed with great medical facilities, making access to healthcare easy for retirees.
The city is not just a haven for those seeking tranquility. It is also known as the windsurfing capital of the world, offering a rush of adrenaline for those interested. Furthermore, Hood River offers plenty of hiking trails for nature lovers. You can also find golf courses for those who prefer a more leisurely pace of life.
2. Lake Oswego
For those looking for upscale living in retirement, Lake Oswego is an excellent choice. This suburb of Portland is known for its friendly and thoughtful neighbors, making it a delightful community to be a part of. With everything needed within a 10-minute drive, including restaurants, grocery stores, and movie theaters, the convenience is unparalleled.
One of the highlights of Lake Oswego is its unique charm. It’s a city steeped in history, with a vibrant culture that’s reflected in its architecture, arts scene, and local events. From the historic Conway House to the iconic Lake Oswego Hunt, there’s always something to explore and discover.
The city also offers a plethora of dining options, with an emphasis on fresh, locally sourced ingredients. Whether you’re a seafood lover or a vegetarian, there’s a restaurant to suit your palate. With a range of shopping options and excellent healthcare facilities, it’s a city that caters to all your needs in retirement.
The Oswego Grill, in particular, is a favorite among residents. However, Lake Oswego’s charm comes with a price. Housing prices here are higher compared to other areas in Oregon, reflecting the upscale lifestyle the city offers.
3. Coos Bay
The serene city of Coos Bay offers the best of coastal living at an affordable price, making it one of the most desirable places for retirees in Oregon. With a significant population over 65, Coos Bay is a thriving community that welcomes retirees. The city is also well-equipped with healthcare facilities, including hospitals within 25 miles of the city center.
However, just like any other city, Coos Bay also has its fair share of challenges. The city has experienced instances of violent crimes and property crimes. Nevertheless, the city’s law enforcement is always working to ensure the safety and security of its residents.
4. Cottage Grove
In Lane County lies the picturesque city of Cottage Grove, known for its rustic charm. Affectionately known as the “Covered Bridge Capital of Oregon,” this city is perfect for those who crave a slower pace of life. With its affordable cost of living, you can spend your days exploring the historic downtown or taking leisurely walks through one of the city’s many parks. The city’s unique blend of small-town simplicity and scenic beauty is a testament to the quality of life that awaits you in Oregon.
The city takes pride in its Covered Bridges Scenic Tour Route, allowing residents to enjoy the stunning landscape. If you’re a retiree who appreciates the beauty of nature, Cottage Grove is a fantastic choice. The city also has several hospitals within 25 miles, providing easy access to healthcare services.
While the city is peaceful and serene, it also has instances of violent crimes and property crimes. However, the city’s law enforcement is proactive in maintaining the safety of its residents. The charm of Cottage Grove, along with its affordable cost of living, makes it a preferred choice for many retirees.
5. Grants Pass
Grants Pass is an Oregon city that sits comfortably along the banks of the Rogue River. It has quickly become a favorite amongst retirees with an affinity for nature and the great outdoors. With a steadily increasing population of nearly 40,000, this charming city is gaining popularity as a perfect retirement destination.
One of the highlights of living in Grants Pass is the outdoor recreation it offers. Nestled in the heart of the Rogue River-Siskiyou National Forest, residents can access a wealth of hiking opportunities. Despite a modest average household income, residents place a high value on the rich experiences and adventures that nature has to offer.
6. Florence
Florence, a small town in Oregon, has been recognized by many as a prime place to retire. Its tranquil ambiance and slower pace of life offer retirees a peaceful setting to enjoy their golden years. The city might be sleepy, but it has a fair share of amenities, including bars and good restaurants.
Overall, Florence offers a relaxed and comfortable lifestyle that many retirees crave. The beauty of the coast, coupled with the small-town charm, makes it an ideal place to retire, unwind, and enjoy the finer things in life.
7. Ontario
Ontario, a captivating community on the Oregon and Idaho border, provides a serene and affordable living option for retirees. With a relatively low median home value, it’s a great place for those seeking to save money during retirement. Despite its tranquility, the city is not devoid of actions, with recent annual numbers of violent crimes and property crimes standing at 95 and 658, respectively.
The city has two hospitals within 25 miles, offering adequate healthcare facilities to its residents. Furthermore, the city’s proximity to Boise, Idaho, and its sublime scenery make it an attractive choice for retirees looking for a simple yet satisfying lifestyle.

8. Prineville
Located on the edge of the Ochoco National Forest is Prineville, a safe and affordable town that is perfect for active retirees. This Oregon city offers an abundance of outdoor activities, such as hiking and exploring the natural wonders of the area. The city has a low number of violent crimes and property crimes, with 40 and 127 reported, respectively, in the most recent year.
Prineville also has one hospital within 25 miles, ensuring healthcare needs are met. The town hosts regular community events at the Crook County Fairgrounds, giving retirees plenty of socializing opportunities. In Prineville, retirees can enjoy a peaceful and engaging lifestyle amidst nature’s beauty.
9. Dallas
Dallas, Oregon, offers a unique charm with its old-fashioned downtown area. The city exudes a sense of nostalgia that many retirees find appealing. Despite its historical charm, Dallas is far from stagnant. The city offers a variety of amenities and experiences that enhance the quality of life for its residents.
Whether it’s the local shops, the vibrant community, or the tranquility of the surroundings, Dallas offers a balanced lifestyle that makes it an ideal location for retirement. In Dallas, retirees can enjoy golden years filled with comfort, leisure, and a touch of adventure.
10. Astoria
Retirement should be a time to embrace tranquility and seek out new adventures. For those craving the allure of coastal living, Astoria, Oregon, could be the perfect fit. Nestled where the mighty Columbia River meets the expansive Pacific Ocean, Astoria presents a wonderful blend of natural beauty and community spirit.
The Oregon coast, with its breathtaking vistas and charming seaside towns, offers a retirement experience unrivaled by any other. Astoria, in particular, is a standout. The city’s temperate maritime climate, with mild winters and cool summers, adds to its appeal. The occasional cloud cover and mist enhance the charm, painting a picturesque backdrop for your golden years.
Life in Astoria presents ample opportunities for outdoor activities. From beachcombing on the nearby Cannon Beach to whale watching, the offerings are diverse and plentiful. The calming sound of waves and the scent of fresh seafood being prepared in local eateries create an ambiance that’s soothing and invigorating at the same time.
But Astoria is not just about the Pacific Ocean and its natural beauty. It’s a place where the pace of life encourages relaxation and reflection. The community is known for its welcoming spirit, making newcomers feel right at home. It’s the kind of place where everyone knows their neighbors, fostering a sense of belonging that’s hard to find elsewhere.
11. Brookings
Brookings, a quaint town in Oregon, is a sanctuary for those who prefer the quiet, slow-paced life of non-urban retirement. With an intimate population mostly of upper-middle-class retirees, it offers a sense of community and tranquility that is often hard to find in bustling cities.
This charming town is often lauded as one of the most beautiful places to reside in the United States, rivaling even the picturesque Carmel in California. Its natural beauty is highlighted by the evergreen Harbor and Brookings, both of which have garnered positive reviews for their stunning views and peaceful ambiance. It’s no wonder retirees find solace and joy in such a serene environment.
For retirees, Brookings offers more than just a visually pleasing landscape. It is a haven where they can enjoy their golden years surrounded by nature and friendly faces. With so much to offer, it’s easy to see why Brookings has become a prime location for non-urban retirements.
12. Ashland
If you’re considering Oregon for retirement, Ashland is one of the best places to retire in the state and is well worth your consideration. Situated just 20 miles north of the California border, Ashland is a vibrant community in southwestern Oregon. Part of the Rogue River Valley, this 11-square-mile enclave is nestled at an elevation of 2,000 feet and is surrounded by nature’s beauty.
The residents of Ashland, totaling over 21,000, are known for their strong sense of community and laid-back vibe. The town itself is recognized nationally for hosting the Oregon Shakespeare Festival, an annual staging of classic and contemporary plays that attracts over 125,000 visitors for nine months each year. This cultural hub, coupled with its small-town charm and scenic surroundings, makes Ashland a top choice for retirees.
Aside from its vibrant cultural scene, Ashland also offers a plethora of recreational opportunities. Its proximity to Crater Lake and the Rogue River provides retirees with countless opportunities for outdoor adventures. Whether you’re exploring the wine country, strolling through its lively downtown, or simply soaking up the southern Oregon sun, Ashland is a retirement paradise that combines cultural richness with nature’s bounty.
13. Roseburg
Roseburg, often known as the heart of the Land of Umpqua, is a haven for those who appreciate the finer things in life. The city is nestled in a recreational region that offers a wonderful blend of history, culture, and outdoor activities. With a high percentage of the population over 65, Roseburg is a popular choice among retirees.
The city boasts several golf courses, providing ample opportunity for leisurely afternoons on the green. But it’s not just about golf; Roseburg is also renowned for its favorable weather, flourishing wine industry, and stunning waterfalls. This combination makes it an enticing option for adventure-seeking retirees who enjoy a balance of outdoor pursuits, relaxed living, and are weather, wine, and waterfalls enthusiasts.

Factors That Determine the Best Places to Retire in Oregon
Before deciding on the best place to retire in Oregon, it’s essential to consider several factors. Each person’s ideal retirement location might differ based on personal preferences, but certain fundamental factors can guide you in your search. These factors help distinguish between a good retirement destination and a great one. Here, we will discuss five vital factors determining the best places to retire in Oregon.
Recreational Opportunities
One of the main attractions of retiring in the Beaver State is the wide range of recreational opportunities. For instance, if you’re an adventure-seeker like my husband and I, you might enjoy Hood River’s kiteboarding scene or Crater Lake’s stunning hiking trails. Southern Oregon’s wine country also offers a sophisticated experience for wine enthusiasts. Plus, the proximity to the California border makes it easy to plan trips to explore another state.
Cost of Living
Affordability is a crucial factor when planning for retirement. Cottage Grove, also known as the ‘Covered Bridge Capital of Oregon,’ is a charming city with a surprisingly affordable cost of living. The median household income and the cost of housing are more reasonable compared to other cities in the United States.
Proximity to Healthcare Facilities
As we age, access to healthcare becomes increasingly important. Towns like Lake Oswego offer close proximity to top-notch healthcare facilities, ensuring good health during our golden years.
Community and Social Engagement
A lively downtown area can provide a sense of community and opportunities for social engagement. For example, the city of Grants Pass has a vibrant downtown area filled with cafes, shops, and art galleries, making it easy to stay socially active and engaged.
Climate
Oregon’s climate varies greatly across the state, from the wet coastal areas to the drier inland regions. Thus, your preference for a specific climate can influence your choice. If you prefer a coastal climate, towns such as Astoria or Coos Bay could be perfect. Alternatively, for a drier climate, you may consider cities in eastern or southern Oregon.
Overall, the best places to retire in Oregon offer a combination of affordability, recreational opportunities, accessible healthcare, a strong sense of community, and a desirable climate. It ultimately boils down to personal preferences and priorities. But with some research, you’re sure to find a city or town in Oregon that checks all your boxes for an amazing retirement.
Frequently Asked Questions
1. Is it expensive to retire in Oregon?
Retirement costs in Oregon can vary depending on various factors. For instance, the cost of living in Lake Oswego, an upscale Oregon city, may be higher than in other places. A significant portion of retirement expenses often goes towards housing and healthcare. It’s important to consider that Oregon has seen its share of property crimes and violent crimes, and these safety considerations can impact where you choose to settle.
2. Does Oregon tax pensions and Social Security?
Yes, Oregon does tax pension income and Social Security benefits. However, the state does offer some tax credits for retirees below a certain income threshold. This means that while some of your retirement income may be taxable, you may also be eligible for certain credits that can offset these taxes. This is another area where financial advisors can provide valuable advice and guidance.
3. Is Oregon a high-tax state?
Compared to other states, Oregon can be considered a high-tax state, particularly regarding income tax. The state has one of the highest income tax rates in the country. However, it’s important to note that Oregon does not have a sales tax, which can balance out the high-income tax for some individuals. Again, consulting with a financial advisor can provide a clearer picture of the tax situation in Oregon and how it may impact your retirement planning.
Wrapping Up
As our Oregon journey ends, it’s important to remember that financial planning is an essential part of the process. This includes managing your retirement income and retirement accounts in a way that will support your lifestyle choices. Considering the affordable cost of living in numerous Oregon cities, your dream retirement is well within reach. Living in Oregon offers an unparalleled retirement experience with its unique blend of urban and natural beauty. From the tranquil coastal towns of the Pacific Northwest to the vibrant cities in the Willamette Valley, there is truly something for everyone.
Active adults will find Oregon particularly appealing, as the state offers a plethora of outdoor adventures. Whether it’s exploring the Land of Umpqua, with its recreational region in the North Umpqua National Park, or attending the famous Oregon Shakespeare Festival, the state guarantees an active and healthy retirement. Each town attracts a different crowd, but all offer the same promise of a fulfilling retirement life. So, lace up your hiking boots, polish your binoculars, and prepare yourself for the next chapter of your life in this beautiful corner of the Pacific Northwest.





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