7 Best Small Towns to Retire in Oregon

You worked hard your whole life, put in your dues, gave your pound of flesh, and now it is your time to shine. Retirement is a phase of relaxation for some, and an opportunity for others to spread their wings. Whatever your personal vision for the sunset years, small towns can help foster it. Escaping the big cities can not only bring a sigh of relief in terms of mental and spiritual metrics, but perhaps most importantly, downsizing to a quieter community can bring financial freedom. Oregon is a gorgeous state from top to bottom, but its cost of living ranks above the national average. These seven small towns, however, are affordable, fun, and sensible places to nestle into at the end of a challenging career. 

Ashland

Though an artist's body may age, the creative spirit is immortal. Ashland, voted one of the best small art towns in America, is an excellent place for lovers of all expressive mediums to settle down. Located in Oregon's Southwest corner, at the base of the Siskiyou and Cascade mountain ranges, this eclectic Jackson County city has lots to offer its senior contributors.

Such fans of the finer things in life can enjoy the annual Oregon Shakespeare Festival and other theatrical performances throughout the year, regular exhibits displayed throughout award-winning galleries, top-tier restaurants, artisanal shops, and the benefits of being so close to California's wine country. Ashland has 1.56 recreational centers and 0.44 retirement communities per 1,000 people. 

Cottage Grove

Cottage Grove not only connotes a lovely retirement community, but the tangible benefits make a compelling objective case. Plunked just South of Eugene, in Lane County, this sub-11,000 resident city (with 16.2% over 65) is as pretty as it is pragmatic. Cottage Grove has twice been awarded the "All-American City" crown – owing to its extensive Covered Bridges Scenic Bikeway, inviting trails, nearby waterfalls, historic downtown, wholesome farmers' markets, and plenty more. The median home value is $192,600, there are four hospitals within 25-miles, and both violent crimes and property crimes show low annual figures. 

Coos Bay

Who doesn't dream of one day living on the water? The bayside city of Coos Bay (sitting on the Pacific Ocean-adjacent body of water by the same name) is somehow beautiful and affordable, but still only has an approximate population of 15,985 residents. Prospective retirees will be in good company in this Coos County community, as around 21.4% of residents are over 65 years old.

The medium home value hangs out around $181,200, there are four hospitals within shouting distance, and violent crime remains low here. The one kicker is that between 2020-2021, 808 property crimes were reported. This is nowhere near the upper rankings for the state, but something nonetheless worth noting. 

Roseburg

For seniors with some pep in their step and/or an adoration for the outdoors, Roseburg is the place for you. This Douglas County city of 23,683 (22.3% over 65) is smack dab in the middle of the Land of Umpqua – a revered recreational region great for hiking, fishing, enjoying a picnic, or touring the numerous wineries.

Roseburg maintains an approachable median home value of $215,000, has two hospitals within 25 miles, and coasts along with modest rates of violent crime. However, this otherwise pristine community does once again post an unfortunate amount of property crime, the highest, in fact, on this list (1,352 incidents in the most recently surveyed year). 

Lebanon

Lebanon is quiet, cute, and well-equipped for an older population. This Linn County city has a population of 18,447 (17.5% over 65), four hospitals within 25 miles, a medium home value of $177,900, and exceptionally low rates of both violent and property crimes. Within the town, there is the soothing South Santiam River, the 100-acre Cheadle Lake, a small Japanese Garden, a brewery, cafe, chocolate company, and all the little pleasantries of a traditional American community.

Plus, a short drive brings one to Brownsville (where Stand By Me was filmed) or the historic downtown of Albany. And if you are feeling drawn to the big city for a weekend, Lebanon is just over an hour from Portland (to the North) and a little under an hour from Eugene (to the South). 

Hood River

Nestled on the river of the same name, and within the shadow of Mount Hood, Hood River has a lot to offer. For starters, this Hood River County city has only 8,313 residents, but about 6.88 medical facilities per 1,000 people. This makes it one of the best places to retire in Oregon in terms of easy access to healthcare. But even though Hood River is a sensible place for those with age-related limitations, it also fosters outdoor recreation of all sorts.

Being on a rural border with Washington, and in the pristine Columbia River Gorge, there are naturally plenty of hiking trails to peruse and camping opportunities to enjoy. Hood River is also considered the wind surfing capital of the world. Whether or not this adrenaline sport is age-appropriate is up to the individual, but in either case, spectating along the river's edge is surely an exciting way to pass a summer day. 

Ontario

Ontario rests on the border of Idaho, within an hour's drive of Boise. This scenic Malheur County city has a moderate population of about 11,645, approximately 18.1% of whom are people over 65 years of age. Budget-conscious retirees will be glad to know that the median home value here sits around $117,800 USD (as of 2021), far below the state's average of $334,100. For those in need of regular assistance (or are anticipating the inevitable events of advanced age) Ontario has 1.17 retirement communities per 1,000 people, 2.71 medical facilities/1,000 people, and two hospitals within a 25-mile radius. And finally, violent crime is quite low in Ontario, although annual property crimes are not exactly negligible. 

Whether you envision passing the afternoons with a good book on a cozy porch-swing, or getting out there and experiencing some culture or the great outdoors, small towns in Oregon can deliver on all fronts. These seven communities have the necessary infrastructure for aging populations, will stretch your hard-earned dollars a bit further, and maintain enough of a social scene to keep seniors young at heart. Enjoy your promised land!