Arched sign across East Main Street in Cottage Grove Historic District Oregon. Editorial credit: Ian Dewar Photography /

13 Best Small Towns to Retire in Oregon in 2024

Oregon has long been a popular retirement destination on the West Coast, offering affordability, natural beauty, and small-town charm. With its temperate climate, rugged coastline, lush forests, and quintessential Pacific Northwest character, the state provides endless opportunities for outdoor recreation and leisurely living. It is the ideal setting to establish a permanent home after calling time on your career.

Factors like reasonable home costs, recreational activities, access to amenities, and overall livability help make these towns a sanctuary for pensioners looking to retire in Oregon. From seaside villages to mountain hamlets, these communities provide retirees with the best of both worlds - an idyllic small-town setting and close proximity to all the amenities one needs to age comfortably.


Aerial view of Ashland, Oregon.
Aerial view of Ashland, Oregon.

This small village in southern Oregon is a renowned cultural hot spot, where award-winning galleries, quaint theater venues, and trendy restaurants, attract all types of characters from around the country. The rural setting is ideal for retirees, providing green nature spaces like Lithia Park and North Mountain Park for their outdoor recreation. Ashalnd’s vibrant art scene presents numerous centers of visual and performance art, including the celebrated Oregon Shakespeare Festival and the Schneider Museum of Art. Meanwhile, ScienceWorks Hands-on Museum will prove invaluable when the grandkids visit by providing the ideal space for them to learn while having fun.

With so many people keen on moving to Ashland, the price of homes has risen above the state average. It takes around $625,000 to acquire a house in the town, but retirees can look forward to a high quality of life.

Lake Oswego

Lake Oswego, Oregon, USA. Editorial credit: Victoria Ditkovsky /
Lake Oswego, Oregon, USA. Editorial credit: Victoria Ditkovsky /

This popular waterfront community in Clackamas County provides residents with a rural atmosphere, comprising multiple green spaces for an easygoing life after retirement. Seniors are spoilt for options when it comes to outdoor adventures, thanks to George Rogers Park and Foothills Park, which both straddle the beautiful Willamette River. A lively local arts scene ensures that the community stays entertained around the year with engaging performances staged at Lakewood Center for the Arts and awesome art pieces exhibited by the Arts Council of Lake Oswego.

The only downside to settling in Lake Oswego is that it will cost you dearly if you plan to acquire a home; the median price here is $1.2M.

West Linn

Willamette Falls Along Willamette River between Oregon City and West Linn Closeup.
Willamette Falls Along Willamette River between Oregon City and West Linn Closeup.

For retirees looking to escape the fast-paced life in the city but still remain within touching distance of its vital amenities, this charming suburb of Portland promises the best of both worlds. West Linn harbors a raft of serene nature spaces for fantastic outdoor experiences, from Camassia Nature Preserve to Mary S. Young Park, where they can indulge in different kinds of recreation like hiking among wildflowers, biking, fishing, and picnicking. The city also boasts the largest waterfall by volume in the PNW, Willamette Falls, a breathtaking sight that draws admirers from around the region.

For wine lovers, Oswego Hills Vineyard has greatly boosted the wine culture in West Linn, promising retirees an endless supply of freshly crafted wines in their sunset years. While the average home price of $799,800 is a tad costly, residents have the luxury of accessing all Portland has to offer in a matter of minutes.

La Grande

A sign letting people know they are at City Hall in La Grande Oregon. Editorial credit: Michael Barajas /
A sign letting people know they are at City Hall in La Grande, Oregon. Editorial credit: Michael Barajas /

La Grande stands out for its theater and arts, boasting a vibrant downtown corridor with art centers like the Elgin Opera House and Liberty Theater. This can be credited to the presence of Eastern Oregon University, which also guarantees retirees academic aspirations and lifelong learning opportunities. An impressive network of parks provides endless outdoor adventures, especially inside the vast expanse of the Hilgard Junction State Park, where activities like hiking, camping, and wildlife viewing await. With a tight-knit community to call home, retirees will have no issues making friends and embracing the friendly demeanor of the locals, best displayed during the La Grande Farmers’ Market. Furthermore, homes are quite affordable in this beautiful town, with the median house listing price at $317,500.


Canby, Oregon. Editorial credit: Michael Warwick /
Canby, Oregon. Editorial credit: Michael Warwick /

A quaint farmers’ market running from May through October showcases the agricultural prowess of this adorable community in Clackamas County while bringing out the close ties that exist between the locals. Fresh retirees not only get friendly neighbors but also enjoy several outdoor adventures around the town, courtesy of venues like Molalla River State Park. This presents everything from hiking and boating to fishing and wildlife viewing.

Senior citizens with a penchant for nostalgic experiences will fancy checking out the Canby Depot Museum. The facility displays a fine collection of antiquities, including cameras, telephones, and a postal service, in one of the state’s oldest railroad stations. Finally, owning a decent home in Canby will cost an average of $649,000, which is the town’s median price.


McDowell Creek Waterfalls Lebanon, Oregon.
McDowell Creek Waterfalls Lebanon, Oregon.

This charming community of Linn County is famous for the century-old Strawberry Festival, a long-held annual tradition that has helped maintain strong ties and harmonious living among the townsfolk. Several nature spots allow retirees to lead an active lifestyle, including Had Irvine Park, which is ideal for hikers looking to explore Oregon’s lovely wilderness. Meanwhile, the Linn County Arts Guild beckons enthusiasts to browse a rich collection of exhibits, featuring art forms like jewelry, photography, and paintings.

Exploring downtown Lebanon exposes retirees to cute social hangouts that they can pop into to meet new friends and chat over a wholesome meal or bottle of beer. The 1874 Bar & Grill is a great example that charms patrons with a laid-back atmosphere. For those planning to buy a home in Lebanon, the median listing price is $452,400, which is below Oregon’s average.


Cityscape at the Silver creek at the city of Silverton, OR, USA.
Cityscape at the Silver Creek in the city of Silverton, OR, USA.

Silverton is strategically positioned 14 miles from Salem, allowing pensioners to access valuable amenities and services in the capital. Despite this proximity, it provides a lovely rural atmosphere that guarantees a slow pace of life tailored for retirement living. Among its many green spaces, Silver Falls State Park is easily the most revered and promises opportunities for an active lifestyle through hiking, biking, and horse riding. Water-based recreations abound at the Silver Creek Reservoir, a popular summer spot where locals converge to enjoy swimming, boating, kayaking, and paddleboarding.

The town also features a bustling restaurant scene, with several joints where seniors can catch up over a hearty meal. Guerra’s Restaurant is among the trendiest spots in town, popular for its delicious Italian cuisine. Furthermore, a median home price of $594,500 is decent considering the town’s proximity to Salem.


Crook County Courthouse at Prineville, Oregon.
Crook County Courthouse at Prineville, Oregon.

Sitting right at the edge of Ochoco National Forest, Prineville allows retirees to spend their golden years surrounded by beautiful nature in an easygoing environment. This also presents numerous opportunities outdoors, with recreations like hiking, kayaking, fishing, and nature viewing awaiting inside the Ochoco Wayside State Park. There is more water-based fun to take advantage of at the Prineville Reservoir, which also offers developed campsites for the ultimate outdoor experience.

Away from the great outdoors, Prineville has multiple indoor attractions that may interest retirees. For starters, Bowman Museum presents a look into local history while Pine Theater showcases family-friendly films tailored for all ages. Finally, a median home cost of $471,400 in the town is almost at par with the state average.


 Western Oregon University sign at the Monmouth campus. Editorial credit: Ian Dewar Photography /
Western Oregon University sign at the Monmouth campus. Editorial credit: Ian Dewar Photography /

Settling in Monmouth allows pensioners to stay active both physically and mentally. This tiny community in Polk County houses the Western Oregon University, which provides a continuous learning opportunity for seniors. Its rural setting assures multiple green spaces with diverse recreations, including Main Street Park and Monmouth Dog Park. Retirees who prioritize wellness and healthy living can take advantage of several fitness stations in the town to stay in top shape, from Monmouth Fitness Club to FireHouse CrossFit.

Monmouth’s youthful college population has led to a vibrant wine and dining scene, with several restaurants serving all types of flavors. If you have a soft spot for Mexican cuisine, you will appreciate the menu served and ambiance of Koyote’s Tacos. Finally, owning a home in Monmouth will cost an average of $434,500.

Cottage Grove

Currin Covered Bridge Near Cottage Grove, Oregon State, US.
Currin Covered Bridge Near Cottage Grove, Oregon State, US.

This historic town in Lane County was popularly christened “Covered Bridge Capital of the West” due to its numerous covered bridges, some listed on the National Register of Historic Places. Visiting the Chambers Covered Railroad Bridge takes you back to the early 20th century when it was built, featuring scenic natural surroundings ideal for relaxing. However, more historical sites hint at the colorful history harbored by Cottage Grove. The Bohemian Gold Mining Museum documents the town’s mining heritage, whereas the Oregon Aviation Historical Society & Museum focuses on regional aviation history.

Retirees can also join community members at the Cottage Theater to catch moving live performances, ranging from plays and musicals to concerts. Finally, homes here cost an average of $616,700, which is slightly lower than the state average.


Riverwalk in Siuslaw River in Florence, Oregon.
Riverwalk in Siuslaw River in Florence, Oregon.

Florence is an exciting haven for retirees planning to live out their sunset years in the serene scenery of the Oregon coast. With senior citizens making up about 36% of the local population, newcomers will have an easy time fitting into the community. A rich history of Florence can be uncovered at different museums in the town, including the Siuslaw Pioneer Museum and the Oregon Coast Military Museum.

Also, there is no shortage of outdoor opportunities, with the Jessie M. Honeyman Memorial State Park providing the perfect playground for adventurers. The park is connected to the Oregon Dunes National Recreation Area, where retirees can explore diverse landscapes to make the most of their time outdoors. Finally, a house in Florence will cost you about $559,000.


 Exterior view of Pietro's Pizza Parlor in Milwaukie, Oregon. Editorial credit: Tada Images /
Exterior view of Pietro's Pizza Parlor in Milwaukie, Oregon. Editorial credit: Tada Images /

If you are looking for a safe spot to retire in Oregon, Milwaukie should feature among your priorities. This Portland suburb hosts a tiny community of about 21,000, which takes pride in its small-town charm and friendly personality. Those interested in familiarizing themselves with the town’s rich past can visit the Milwaukie Museum to browse an awesome collection of artifacts. Meanwhile, North Clackamas Aquatic Park is an excellent spot to spend time with family when the grandkids pay a visit. Milwaukie has no shortage of outdoor opportunities. At Ardenwald Park, pensioners will find a cozy green space with cute walking paths and a variety of sports amenities. A median listing price of about $500,000 means that homes in the town sell for almost the state average.


Alloro Vineyards, Sherwood, Oregon.
Alloro Vineyards, Sherwood, Oregon.

Just outside of Portland, Sherwood invites pensioners to settle in a safe community that balances indoor and outdoor pursuits to keep its residents entertained. A buzzing historic downtown offers a variety of hangouts where retirees can spend free time, including hunting for unique treasures at Railroad Street Antique Mall. Wine tasting and drinking are a part of the local community, as is apparent from the various wineries and vineyards dotting Sherwood. Those with a taste for fresh wine can visit Alloro Vineyard to sample some of the best local offerings.

For the outdoor inclined, Snyder Park is among the more popular outdoor spaces in the town. It is an excellent spot for lazy walks and undisturbed picnics in a laid-back environment. Meanwhile, those planning to invest in a home should know that the median listing cost is $692,500.

Oregon offers excellent small-town options for those seeking a relaxed retirement lifestyle on the scenic West Coast. The towns featured span from coast to coast, mountains to valleys, providing a diversity of natural settings and character. With amenities like outdoor recreation, cultural opportunities, and healthcare access in friendly communities, these places allow future retirees to enjoy the natural beauty of the Pacific Northwest while aging comfortably. Spending your golden years in any one of these top towns to retire in Oregon is sure to provide lifelong enjoyment and memories.

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