Discover Your Next Chapter in Oregon
From misty coastal towns and lush valleys to high desert plateaus and quirky urban hubs, Oregon welcomes retirees with its rich landscapes, progressive spirit, and vibrant communities. Whether you're drawn to the arts and culture of Portland, the scenic wine country of the Willamette Valley, or the serene pace of life in coastal hamlets, Oregon has something special for everyone over 65.
This guide explores why so many are choosing Oregon as the backdrop for their next chapter — and how you can make the most of life in the Beaver State.
Why People Love Oregon
Scenic Wonders in Every Direction
From the rocky Pacific coastline to the forested Cascades and expansive high desert, Oregon offers breathtaking variety for outdoor lovers. The state's four-season climate brings colorful springs, sun-drenched summers, vibrant autumns, and snowy winters in higher elevations — ideal for those who enjoy seasonal change.
Personality-Packed Places to Call Home
Each Oregon town brings its own character. Eugene combines college-town energy with a relaxed pace. Bend offers high desert beauty and endless recreation. Coastal towns like Astoria and Florence exude charm and history, while Portland’s eclectic neighborhoods cater to every interest.
Sustainable, Active Living
With a strong emphasis on sustainability, Oregon cities are designed for walking, biking, and public transportation. Farmers markets, co-ops, and eco-conscious neighborhoods are widely available, making it easy to lead a healthy, environmentally aware lifestyle.
Living Well in Oregon
Easy Access to Nature & Recreation
Whether it’s kayaking on the Columbia River, hiking through old-growth forests, or biking wine country trails, staying active comes naturally in Oregon. State and national parks, forest lands, and public beaches ensure countless ways to enjoy the outdoors — many of them free or low-cost.
Health & Wellness, Oregon-Style
Oregon is home to top-rated medical centers and progressive healthcare systems, including providers specializing in Medicare and senior care. Wellness is a way of life here, with communities offering yoga studios, holistic health services, and outdoor fitness options tailored for older adults.
Lifelong Learning & Culture
Oregon encourages curiosity and creative expression. Public libraries, university extension programs, and community centers host events, classes, and lectures. Whether it’s pottery in Ashland, writing workshops in Corvallis, or volunteering at local museums, opportunities to grow and give back abound.
Explore the Best of Oregon Living
Portland
Oregon’s largest city is a haven for retirees who enjoy arts, food, and nature — all in one place. With its renowned healthcare systems, public transportation, and walkable neighborhoods, Portland offers both convenience and culture. Seniors appreciate the city’s abundant parks, thriving farmers markets, and access to lifelong learning through local universities. Despite its big-city energy, Portland’s neighborhoods feel like close-knit communities.
Eugene
Home to the University of Oregon, Eugene blends academic charm with natural beauty. Nestled along the Willamette River, it features scenic bike paths, public gardens, and a flourishing arts scene. Eugene’s progressive vibe and health-conscious culture make it an appealing choice for active retirees looking to stay intellectually and physically engaged.
Bend
Located in Central Oregon, Bend is a growing favorite for retirees drawn to outdoor adventure and small-town charm. With over 300 days of sunshine a year, Bend is perfect for hiking, skiing, and kayaking. The city also boasts a strong medical community, vibrant local breweries, and cultural amenities — all in a relaxed, scenic setting.
Ashland
Renowned for the Oregon Shakespeare Festival, Ashland is a cultural gem in southern Oregon. With a walkable downtown, boutique shops, and a strong community focus, it attracts retirees who value the arts and a slower pace of life. The nearby Lithia Park and access to nature trails make it a top choice for those who want both tranquility and enrichment.
Salem
As Oregon’s capital city, Salem offers retirees a blend of historic charm and modern convenience. Nestled in the heart of the Willamette Valley, Salem is known for its scenic beauty, local wineries, and rich cultural heritage. The city features numerous parks, a vibrant arts scene, and excellent healthcare facilities. With its relaxed pace and strong sense of community, Salem is an ideal spot for those seeking comfort, accessibility, and enrichment in their retirement years.
Hillsboro
Located in the Tualatin Valley just west of Portland, Hillsboro is a growing tech hub that retains a warm, small-town feel. Retirees are drawn to its abundance of green spaces, modern medical centers, and diverse cultural offerings. Hillsboro’s walkable downtown, weekly farmers markets, and proximity to wine country and nature trails offer a balanced lifestyle for those who enjoy both convenience and outdoor exploration.
Medicare in Oregon
Oregon offers a diverse range of Medicare Advantage and Medicare Supplement plans, with options that vary by region, county, and ZIP code. In metro areas like Portland, Eugene, and Salem, residents benefit from a broad network of providers and plan types offered through major healthcare systems such as Providence Health, Legacy Health, and Oregon Health & Science University (OHSU). Many plans include extras like dental, vision, hearing, fitness programs, and over-the-counter benefits — though these can vary depending on your specific location.
In rural and coastal areas of Oregon, coverage may be more limited or localized, making it especially important to compare your options carefully. Differences in provider networks, pharmacy access, premiums, and plan rules can have a big impact on how well a plan meets your medical and financial needs.
Fortunately, finding the right Medicare coverage in Oregon doesn’t have to be complicated. Licensed Medicare brokers can help you compare plans based on your healthcare priorities, budget, and lifestyle. Their guidance is usually free and can make it easier to avoid coverage gaps, reduce out-of-pocket costs, and understand your benefits — whether you’re aging into Medicare or moving to Oregon from another state.
We're Here to Help
If you're new to Medicare or exploring your plan options in Oregon, we’re here to help you feel confident in your choices. Whether you're choosing coverage for yourself or assisting a loved one, our local Medicare experts are ready to walk you through the process and connect you with plans that fit your life.