Senior Resources » Retiring in Oregon? Here are the BEST Small Towns for Retirees Looking to Downsize!

Retiring in Oregon? Here are the BEST Small Towns for Retirees Looking to Downsize!

Some of the most favored towns in Oregon are small to medium-sized communities that offer a mix of the great outdoors with close proximity to the city. Some towns are resort-like in nature while others are rustic gems from the Wild West. No matter what kind of town you are drawn to, one thing is clear – Oregon has something for every heart and palette.


Ashland, OR

Duffy Lake, Oregon

Combining culture with recreation, Ashland is lauded as one of the finest towns in America. The community is famous for its Shakespearean Festival and free-spirited university. Gourmet shops and bed-and-breakfasts line the streets. The backdrop of the town boasts the beauty of evergreen and impressive peaks.

Astoria, OR

Located on the Pacific Ocean, Astoria offers a beautiful coastal community smack dab in the center of forested hills and the Columbia River outlet. The downtown offers a wide variety of shops that appeal to nearly every genre, from down-to-earth to the upper shelf. Victorian structures and museums dot the town, adding to its unique charm.


Bend, OR

Located in the heart of Oregon, Bend is one of the recreational hubs of the state. With Mirror Pond situated in the heart of downtown and the backdrop of the Cascades, Bend provides beauty and nature all wrapped up into one. Once an old lumber milling community, Bend provides lavish parks, distinct specialty shops, and more.

Cannon Beach, OR

Artists from around the world need to apply! Cannon Beach is an art lovers’ dream, complete with a quaint little village, unique shops, and the majestic Haystack Rock. The community sits along the beautiful Pacific Ocean and offers wooded hills for hiking, natural amphitheaters, and meticulously groomed gardens.

Hood River, OR

Hood River sits along the Columbia River waterfront and offers majestic views of the gorge. The downtown is a mix of both historic and modern buildings. Fruit trees frame the area. Windsurfing championships compete each year in this buzzing community.

Joseph, OR

Looking for some laid-back living? Joseph, Oregon may be the gem you have been longing for. Known as Oregon’s hidden jewel, Joseph is situated on Wallowa Lake and offers cabin living, boat exploration, and lots of room to hike.


McMinnville, OR

Located in the heart of Oregon’s wine country, McMinnville offers a slow and relaxed pace with more than fifty wineries. Linfield College sits in the center of the town and brings a mix of old and young to the community.

Newport, OR

Newport is known for its tourism and deep-sea fishing. The coastal town offers rich sea air and the smell of seagulls, not to mention a beautiful harbor and lots of saltwater taffy. Art galleries, antique shops, and plenty of seafood can be found in this fun-loving community.

Seaside, OR

Seaside is a premier coastal town located along the western side of Oregon. The area offers outdoor recreation opportunities like no other place. Equipment rental shops line the waterfront and a casual promenade offers souvenirs galore.

Sisters, OR

The backdrop of this charming western community is the grandeur of the three “sister” mountain peaks – Faith, Hope, and Charity. Alpine recreation abounds and the downtown showcases gourmet food shops, antique stores, art galleries, delightful restaurants, and plenty of inns for a good night’s rest.

Looking For More in Oregon?

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Originally published January 31, 2024


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