8 Best Towns In Oregon For Retirees
Although Oregon is not among the cheapest places to retire (the median listing price in Oregon as of April 2025 was $575,000), it boasts a stunning coastline, majestic mountains, and a vibrant cultural scene. Additionally, the climate is generally tolerable and, in most cases, easy to cope with. The best part? Oregon exempts Social Security benefits from taxation. But which are the best spots in Oregon to retire? WorldAtlas has considered several factors, including proximity to reputable medical hospitals, and presents below the 8 best towns in Oregon for retirees.
Ashland
Ashland, the theatre hub of the Pacific Northwest, has been a cherished name in retirement circles for a while now. It is tastefully positioned between the Siskiyou and Cascade Mountain ranges and boasts a relatively mild climate that suits all kinds of outdoor recreational activities. The Oregon Shakespeare Festival, one of its most well-known features, is among the largest regional repertory theaters in the country. Not only that, it boasts the oldest existing full-scale Elizabethan stage in the Western Hemisphere. Ashland is also a college town and hosts Southern Oregon University. If you want a place where you can mingle with young people, so you can imbibe a bit of their optimism and camaraderie, look no further.
Moreover, the town is walkable, meaning you can live here and regularly tour the town without a car. Pleasure spots include the highly impressive Lithia Park, a 100-acre space with grassy lawns and ponds; Emigrant Lake, and the beautiful trails that run around it; and the Siskiyou Mountains. On healthcare access, Asante Ashland Community Hospital is in town, while the award-winning Asante Rogue Regional Medical Center is conveniently located in neighboring Medford. The median listing home price in Ashland was $600,000 in May 2025, which is not significantly above the statewide median of $575,000.
Newberg
If you love wine, outdoor action, and being close to a university so you can continue learning new stuff every day, Newberg is a fantastic retirement option. You can have quiet retreats at places such as the Champoeg State Heritage Area, Rogers Landing County Park, a pretty park that overlooks the Willamette River where one can swim or boat, and the Potter's Vineyard & Clay Art Gallery, if you believe good wine is part of what makes retirement beautiful. Other notable mentions include George Fox University, the well-rated Friendsview Retirement Community, and the Chehalem Cultural Center, which regularly puts up fun-filled events for the community. Keep in mind that Providence Newberg Medical Center is in town and is a 2023 winner of the Gastrointestinal Care Excellence Award. In April 2025, the median listing home price in Newberg was $577,000.
Silverton
Silverton is the gateway to Silver Falls, the largest state park in Oregon. Expect more than 35 miles of backcountry trails, most of which are ideal for hiking, biking, and horseback riding. It is also home to the famous South Falls, a 177-foot curtain of water that is part of the Trail of Ten Falls, a spectacular, nationally recognized hiking trail that snakes through the woods. Within the precincts of town is the scandalously beautiful Oregon Garden, a swoon-worthy space to smile with flowers and experience reflecting pools. Also, Coolidge McClaine Park is a cool place to enjoy a picnic lunch as you listen to the melodious hum of a beautiful creek. You also have a sunny dog park for your furry companion, the highly rated Roth's Fresh Markets, and Legacy Silverton Medical Center. In April 2025, the median listing home price in Silverton was $634,900, which is within a reasonable range of the statewide median.
Florence
The prospect of spending your golden years on the Central Oregon Coast, with stunning ocean views and a relatively more pleasant coastal climate, is something any retiree will want to seriously consider. Darlingtonia State Natural Site has a boardwalk where you can stroll and see the much-talked-about carnivorous plants, while Three Rivers Casino Resort has a non-smoking area to play slots and get entertained. South of town is the Jessie M. Honeyman Memorial State Park, which has a family-friendly atmosphere and beautiful campgrounds for getting intimate with nature. If you love retiring next to the water, you have access to more than 15 lakes, many of which offer plenty of fishing opportunities. Bonus point? PeaceHealth Peace Harbor Medical Center is right in town, so no burning fuel to see a doctor. The median listing home price in Florence was $546,500 in May 2025.
Baker City
One of the most enticing draws to retiring in Baker City is its affordability. The median listing home price in Baker City is $355,000. By Oregon standards — or the Pacific Northwest’s — this price point is difficult to beat. Baker City is in eastern Oregon and boasts a historic small-town charm. It has well-preserved architecture, beautiful views of the Blue Mountains, and plenty of desirable amenities, including Saint Alphonsus Medical Center-Baker City, a Level IV Trauma Center with an Emergency Department. The hospital has been part of Baker County for about 113 years. If you are keen on outdoor adventure opportunities, you have Philips Lake; Powder River Recreation Area, a relaxing space loved for its magnificent forests and clear rivers and streams; and Central Park, a nice place to rest, walk, or enjoy beautiful river views.
McMinnville
In 2018, Forbes named McMinnville the best place to retire in Oregon. It singled out a high number of physicians per capita, good air quality, and a low serious crime rate. McMinnville is in Oregon’s wine region and will see a retiree exploring several wineries and flavours in his or her sunset years. You are surrounded by several outdoor venues, including Tice Park for mid-morning strolls, Michelbook Country Club for an afternoon round of golf, and the South Yamhill River. The best part is that Portland is less than an hour away, meaning fantastic access to big-city amenities. If worried about healthcare access, Willamette Valley Medical Center is in town, while the award-winning Providence Newberg Medical Center is a heartbeat away in neighbouring Newberg. The median listing home price in McMinnville was $527,500, significantly lower than the statewide median.
Grant Pass
With a population of about 40,000, Grant Pass has the energy and vibrancy of a big town, but retains many desirable aspects of a community-focused small town. You are surrounded by incredible natural beauty, the kind that subconsciously lifts your moods and makes every day worth looking forward to. The Rogue River, which flows through the town, is an idyllic spot for fishing, rafting, and other boating adventures. The pine-speckled Rogue River-Siskiyou National Forest is an amazing space with river accesses, campgrounds with fire rings, and picturesque hiking trails. The best part? It spans close to 2 million acres. If a good hospital is a deal-breaker, you have the Asante Three Rivers Medical Center, which won the Patient Safety Excellence Award in 2024. In May 2025, the median listing home price in Grants Pass was $499,000, a price point that is way lower than the statewide median.
The Dalles
The Dalles is in the picturesque Columbia River Gorge and offers more sunshine than towns on the other side of the Cascades. With Portland just over an hour away, a retiree here can access top-notch big-city amenities on a whim. Moreover, you are close to the Mount Hood National Forest, which offers beautiful hiking trails along with stunning views of Mount Hood. Keep in mind that the Deschutes River State Recreation Area is even closer and is a surreal riverside retreat featuring campgrounds, scenic trails, and water recreation. You also have a community college, a nice little library, and the Adventist Health Columbia Gorge, ranked among America’s 50 Best Hospitals for Outpatient Prostate Care. As per realtor.com, in May 2025, the median listing home price in The Dalles was $519,900.
The Takeaway
You don't hear this often, but Oregon boasts some of the most beautiful landscapes in the world. Think of a jaw-dropping coastline with gorgeous beaches and delicious views, rugged mountain backdrops, and peaceful wine regions. Some locations buzz with college-town energy, others soothe with soft sands and cool ocean breezes. The choice is yours.
