8 Most Comfortable Oregon Towns For Seniors For 2025
Oregon is a diverse state that offers beautiful and changing environments. From blizzards at Mt. Hood to mild coastal weather, Oregon offers towns suited to nearly every climate preference.
Oregon also offers some of the most comfortable towns where seniors can retire. With everything from Shakespeare Festivals, 1.5 miles of an exhilarating Crater Lake Zipline, and Sea Lion Caves to numerous wineries, breweries, craft shows, and unique, comfortable dining experiences, it ensures enjoyable weekends for residents and visitors alike.
Ashland
Ashland, Oregon, is a small town with a population of around 21,000 people. In southern Oregon, Ashland offers a mild climate, a welcoming atmosphere, and numerous activities for seniors to enjoy. Providence Medford Medical Center is part of the third-largest healthcare system in the country, providing exceptional healthcare options for the Ashland area. Ashland also attracts alternative healthcare providers, such as acupuncturists and homeopaths, and features the Rogue Community Health Center, which offers a sliding-fee scale for those on a budget.
The world-renowned Oregon Shakespeare Festival presents numerous Shakespeare plays, and backstage tours offer a glimpse into the rich history of the theatre. The Ashland Mystery Festival in the fall offers Sherlock Holmes-style fun and entertainment, featuring author panels, immersive mystery events, and murder mystery dinners. The Schneider Museum of Art at Southern Oregon University displays an extensive collection of art and culture. Outdoor adventures abound in Ashland, from white-water rafting on the Rogue or Upper Klamath Rivers to scenic hikes and picnics at the Grouse Gap Shelter on the Pacific Crest Trail.
After a weekend of fun, residents often unwind at one of Ashland’s 100-plus restaurants. Visitors can try Beasy’s on the Creek to enjoy dining with views over the valley and Ashland Creek.
Klamath Falls
Nicknamed the "Sunshine City of Oregon," Klamath Falls makes an ideal retirement community, boasting mild weather and ample sunshine throughout the year. With a population of less than 25,000, Klamath Falls has a lower cost of living compared to the state average in Oregon.
Klamath Falls is home to Sky Lakes Medical Center, a full-service regional hospital offering specialized senior care and rehabilitation programs, ensuring accessible healthcare within city limits.
One of the oldest birding festivals in the U.S. is at the Klamath Basin. It's one of the most critical migratory paths, and more than 350 species of birds can be sighted there. Klamath Falls is also home to Crater Lake and Oregon's longest zipline. Crater Lake Zipline features 9 ziplines, including two quarter-mile lines, two rappels, and two sky bridges.
For those interested in relaxing shows, the Ross Ragland Theater offers a variety of performing arts, and the Favell Museum provides guided tours of Native American and Western art exhibits.
After a day exploring downtown antique shops, museums, and consignment stores, many residents relax at the Gathering Grounds Cafe and Roastery for an outdoor snack on wooden tables and fascinating surroundings.
Astoria
Astoria is on the Columbia River, near the Pacific Ocean, and boasts a laid-back atmosphere and a coastal climate that suits a more relaxed lifestyle. With less than 10,000 residents, Astoria offers a perfect mix of rich history, as the oldest U.S. settlement west of the Rocky Mountains, and picturesque beauty with panoramic views.
A fishing village with Victorian-style houses, Astoria is famous for being the filming location for "The Goonies" and "Free Willy" movies. It's also home to the Columbia River Maritime Museum and the Lewis and Clark National and State Historical Park. A vibrant downtown area offers unique restaurants, shops, and microbreweries.
For healthcare access, Columbia Memorial Hospital provides comprehensive medical services, while several assisted-living communities and home-care providers support Astoria’s older residents.
Weekends often include rides on the Astoria Riverfront Trolley or tours of the lightship Columbia at the Maritime Museum, followed by live music and riverfront dining at the Bridgewater Bistro along the Astoria Riverwalk.
Jacksonville
Jacksonville is a unique, artsy community with fewer than 5,000 residents. Retirees seeking a small-town feel with a strong sense of community and warmth will find Jacksonville an excellent choice for a retirement home. Jacksonville's entire downtown area is listed on the National Register of Historic Places, and the town got its name from Jackson Creek, which runs through the community and boasts the distinction of being the site of one of the first placer gold claims in the area.
Although Jacksonville is small, seniors benefit from its proximity to Asante Rogue Regional Medical Center in nearby Medford, one of southern Oregon’s top hospitals, as well as local wellness clinics and pharmacies.
Not only is Jacksonville filled with history, but it's also home to a thriving culture, flourishing tourism, and beautiful surrounding hills and mountains filled with greenery, and possibly a hint of gold. Budget Travel Magazine named this special town one of "America's Top 10 Coolest Small Towns" because of its many benefits.
Despite its size, Jacksonville offers a wide range of recreational opportunities to suit every interest. The summer season features the Britt Music and Art Festival, showcasing world-class artists across multiple genres. Numerous independently owned shops and restaurants fill the downtown area, from Willowcreek Gifts, which offers gifts for visiting family, and the Bella Union Restaurant, which provides dining beneath a canopy of trees.
The area’s hiking, biking, and wine-tasting options make Jacksonville a comfortable spot for enjoying a slower-paced lifestyle.
Dallas
Dallas has a population of less than 20,000 and serves as the county seat for Polk County, Oregon, making it easy to attend to business matters. Rolling hills and farmland surround this small town, and there's already a large percentage of seniors living in the area, along with several retiree centers, including the Dallas Retirement Village. There's also more affordable housing, making it a great option for those living on a fixed budget.
Dallas hosts Salem Health West Valley Hospital and the well-known Dallas Retirement Village, both key resources for long-term care and rehabilitation within Polk County. The city park spans over 35 acres of lush greenery and features a distinctive arboretum with shaded walking paths beneath a canopy of trees. The Basket Slough Nature Preserve is nearby, giving more opportunities to enjoy hiking or biking in nature. Spring and summer festivals like Bounty Market and Krazy Dayz make finding nearby entertainment a breeze, and there's even mushroom hunting in the woods in autumn.
One of the best aspects of the area is its low-density growth, which allows residents to live in houses instead of apartments and enjoy their own yards and gardens. The Polk County Historical Museum offers exhibits on the area's history, followed by an evening at the Dallas Cinema featuring modern hits and classics, with either a modern hit or a familiar classic.
McMinnville
Another county seat, and the most populous town in Yamhill County, with a population of around 35,000, McMinnville is a great choice for frugal renters and retirees on a fixed budget. It offers a lower cost of living, a suburban feel, urban amenities, and a small-town atmosphere. In the heart of Oregon's wine country, there are numerous options for wine tastings and winery tours, including the Brittan Vineyards, where the famous Oregon Pinot Noir is grown.
McMinnville boasts a thriving artistic community, complemented by numerous options for natural healing and care. From Alderwood Massage Therapy to Boersma's Sewing Center, retirees can find numerous opportunities for relaxation and hobbies to enjoy a slower-paced lifestyle. Residents have convenient access to Willamette Valley Medical Center, offering emergency care and a senior wellness program, plus several assisted-living communities in town.
Visitors and new residents often spend a weekend exploring one of McMinnville’s most notable historic attractions. The Evergreen Aviation and Space Museum is the home of the world's largest wooden flying boat, the "Spruce Goose." More than 200 historic aircraft and spacecraft can be seen, and Oregon’s largest large-format 3D theatre offers an enjoyable way to end the week.
Florence
At the mouth of the Siuslaw River on the Oregon coast lies the small town of Florence. Filled with history, beautiful scenery, and fun activities, Florence has a senior population of over 40% among its slightly over 10,000 residents, with the average age being around 50. Retirees will fit right into the culture and community, enjoying options for a lower cost of living and a milder climate. Florence also supports retirees through PeaceHealth Peace Harbor Medical Center, local senior centers, and in-home care options, offering reliable medical and wellness services.
The Siuslaw Pioneer Museum offers a mapped, self-guided tour of downtown’s historic sites. Many spend the day at the Sea Lion Caves, where sea lions are often visible in their coastal habitat. The 19th-century Heceta Head Lighthouse provides views of seabirds and migrating whales. Outdoor recreation continues at the Oregon Dunes National Recreation Area, where some dunes reach heights of 500 feet, making it ideal for photography and scenic hikes.
Miles of uncrowded, sunny beaches by the Pacific Ocean provide quiet stretches of sand ideal for reading and listening to the surf. Afterward, coastal fare at the historic Beachcomber Pub & Grill on Bay Street completes a relaxed seaside day.
Hood River
A bustling port on the Columbia River, Hood River is named after the nearby Hood River, offering plenty of nearby water activities. With a population of less than 10,000, Hood River's location, set against the stunning views of the Columbia River Gorge, makes it an idyllic spot for a retirement home. Within the city, Providence Hood River Memorial Hospital offers emergency and specialty care, ensuring seniors have medical support without needing frequent trips to Portland, which is an hour away. Known as ‘The Windsurfing Capital of the World,’ Hood River offers ideal conditions for water sports such as kiteboarding and windsurfing. Also, its close location to Mt. Hood offers a chance to try skiing and snowboarding.
The Hood River History Museum details the region’s Native American heritage and pioneer history. The Hood River Distillers Tasting Room offers samples from many local wineries and breweries. Vintage bottles, ancient equipment, and Prohibition-era stories will offer a deeper look into the area’s historical legacy. Hood River provides an ongoing venue of quilting and craft shows, and the Spirited Roots Farm Fall Workshops provide additional opportunities for crafts and seasonal learning.
There are also plenty of unique dining options, such as the Egg River Cafe and the Solstice Wood Fire Cafe and Bar, to enjoy after a busy day of exploring.
Choosing the Right Oregon Town for Retirement
When choosing the most comfortable place to retire in Oregon, community and atmosphere play a significant role in selecting a forever home. Access to amenities and healthcare is essential, but cost of living, climate, and pace of life can differ widely. Towns like Ashland and Hood River offer active, culture-rich lifestyles, while places such as Dallas and Klamath Falls provide affordability and peace. Coastal towns like Florence and Astoria trade convenience for scenic beauty and ocean air. Each option offers a balance of comfort, accessibility, and lifestyle that helps define what retirement in Oregon can truly feel like.
