11 Best Places To Retire To In Oregon (According To Locals)

When most people (my parents included) start thinking about where they want to retire, the Pacific Northwest is a common destination.

However, those who are retiring without boatloads of money quickly rule out Washington and Southeast Alaska because of their insane cost of living.

Which leaves Oregon.

So, assuming you are attracted by Oregon’s amazing outdoor activities, mild weather, proximity to the ocean, and dozen of other amenities, where should you end up?

The location you choose to settle down in your golden years can be the deciding factor of whether you get to enjoy a close-knit community with great friends and scenery…or you spend your last years yelling at punks to stop peeing on the mailbox of your 400 square house with no yard in Portland.

Small towns sound like the winner, right? So which ones?

Luckily, whenever we travel we take the backroads which have introduced us to some of what I think are the most interesting small towns in Oregon.

So, without further ado, here’s my list.

You’ll likely notice a common theme with many of these towns, however. I chose small towns within proximity to both amenities and outdoor opportunities. If you want to retire to the city or to the woods and never be seen again, these might not be for you!

11 (Mostly) Small Towns In Oregon For The Perfect Retirement

1. Joseph

Winter view of Wallowa Mountains near Joseph Oregon, USA

When it comes time to retire, many people dream of moving to a quiet, picturesque location.

For you, that place might be Joseph, Oregon.

Nestled in the Wallowa Mountains, Joseph is a small town with a big heart. The people here are warm and friendly, and there is a strong sense of community.

Joseph is also home to some of the most beautiful scenery in the country. From the towering mountains to the glimmering lakes, there is no shortage of natural beauty. And, with plenty of hiking and biking trails, retirees can stay active and enjoy the outdoors.

If you’re looking for a place to retire where you can feel relaxed and connected to nature, Joseph, Oregon may be the perfect fit.

2. Astoria

City of Astoria, Oregon, and the Astoria Megler bridge spanning the Columbia River

If you’re looking for a place that combines stunning natural beauty, coastal beauty, and a relaxed, small-town vibe, Astoria, Oregon, might be the perfect spot.

Nestled between the Pacific Ocean and the towering peaks of the Coast Range, Astoria is surrounded by natural wonders, and, with a population of just over 10,000, it’s a perfect size.

In addition to its scenic location, Astoria is also home to a thriving arts community. The city’s historic downtown is dotted with galleries, studios, and theaters. There’s always something going on here from live music to farmers’ markets.

And, if you’re looking for a little adventure, you can always hop on a charter boat and go whale watching or deep-sea fishing. So whether you’re looking for relaxation or excitement, Astoria has something to offer.

3. Baker City

Nestled in the foothills of the Blue Mountains, Baker City offers stunning views of both mountains and plains.

The town is also home to a variety of shops and restaurants, making it the perfect place to while away your retirement years. In addition, Baker City is within driving distance of both Boise, Idaho, and Portland, Oregon, making it easy to stay connected with family and friends.

If you’re looking for a place to get active in retirement, Baker City also offers plenty of opportunities for hiking, biking, and fishing.

4. Brookings

Even though it’s number 4 on this list, Brookings is the number one destination for many people who want to retire to Southern Oregon.

It’s large enough to provide a Fred Meyer but small enough that you’ll still know all of your neighbors (and probably see them at Fred Meyer).

With a mild climate and plenty of things to do, it’s no wonder that Brookings is a popular retirement destination. The town has a reputation for being friendly and welcoming, and there are plenty of activities to keep retirees busy.

From fishing and hiking to playing golf or exploring the nearby state parks (and campgrounds), there’s something for everyone in Brookings.

It’s also worth noting that Brookings is something of a unicorn in the area in that it actually provides a decent level of healthcare. With a hospital and several medical clinics, many people in the area actually end up coming into Brooking for treatment.

5. Bend

Aerial view of the Old Mill District in Bend, Oregon.

In the past, Bend, Oregon has been a destination for hipsters and mountain bikers. However, the retirement community has latched onto it for its mild weather and central location to all of Oregon’s amenities.

The city is located in the foothills of the Cascade Range, offering residents easy access to skiing, hiking, and other outdoor pursuits.

In addition, Bend is home to a vibrant arts scene, with numerous galleries and performance venues so you’ll never be bored no matter what you’re into!

Bend is one of the larger cities on this list but it’s green enough and spread out enough that, as long as you’re not in the downtown area, you can still get most of the small-town perks that are available elsewhere.

6. Hood River

Mount hood and hood river city

Hood River is a beautiful town nestled in the Columbia River Gorge.

Like almost every other small town in the PNW, Hood River offers plenty of opportunities for outdoor activities such as hiking, biking, and kayaking. However, there are also several golf courses and wineries in the area for a more traditional retirement buffet.

The cost of living in Hood River is relatively high, but you’ll be able to find affordable housing options if they are willing to look for them (especially compared to other areas in the PNW).

Overall, Hood River is an ideal place to retire if you are looking for a town with plenty of things to do and a cool, dry climate. If you are looking for the soggy rain-soaked version of the PNW, Hood River isn’t it!

7. Yachats

Oregon Coast Highway 101 winding Yachats

If you’re even driven the Oregon Coast you’ll likely remember that there’s something special about the small town of Yachats. Nestled on the coast between Newport and Florence, this quiet community is the preferred place for a large number of retirees.

The pace of life is slow and peaceful, and there’s no shortage of things to do. From hikes and bike rides along the 8 miles of coastline to exploring the tide pools or skiing at Mount Bachelor, there’s something for everyone in Yachats.

And with an annual average rainfall of fewer than 50 inches, it’s the perfect place to enjoy the outdoors.

8. Depoe Bay

If we leave Yachats and move a bit further up the coast we’ll find the charming city of Depoe Bay just on the other side of Newport.

There are several golf courses in the area, as well as tennis courts and hiking trails which make it appealing to people of all ages. But especially for those with money to actually rent a cart while golfing…

Unusually for a town of its size, Depoe Bay also has a public library and a community center so you’ll have something to do on rainy days.

As with most seaside towns in Oregon Depoe Bay is full of small restaurants and diners where you easily become a regular and get to know people.

So if you’re thinking about retiring and don’t want to break the bank, consider making Depoe Bay your new home!

9. Salem

Downtown Salem as viewed from the top of the Oregon State Capitol building

Now, I’m afraid it’s time to move on from small towns to a few other mid-sized options for the last three. It might be surprising to some, but many people want to retire to nice dinners, a county club, and some decent shopping. None of the small towns above have much to offer in the way of vibrant urban life, no matter how much I love them.

So, starting here with Salem, let’s take a look at a few other great retirement locations that won’t suck out your soul and waste your time with insane traffic.

With its mild climate, diverse cultural scene, and proximity to both the mountains and the ocean, I guess it’s really no wonder that Salem, Oregon is a popular retirement destination.

The state capital is also home to a number of excellent hospitals and medical facilities, making it a great place to live for seniors who want access to quality healthcare.

And with its low cost of living and abundance of recreational opportunities, Salem offers retirees an appealing mix of affordability and amenities.

As with most cities in the PNW, there’s still a huge emphasis on “living green” so there are plenty of trees and open spaces to keep people from feeling stifled.

10. Newport

Boats and houses in Yaquina Bay in Newport, Oregon

Situated on the Oregon Coast, Newport is a charming town that offers a relaxed lifestyle and easy access to some of the state’s most beautiful scenery. With a population of just over 9,000, Newport is really just a large town but is sizable enough is large enough to offer a variety of amenities.

The town is home to an interesting arts scene (spoiler – everyone in the PNW fancies themself an artist…), as well as plenty of opportunities for outdoor exploration, from hiking and biking to kayaking and whale watching.

Newport’s mild climate makes it an ideal place to retire, and the low cost of living and lack of traffic congestion are also appealing features. If you’re looking for a place to enjoy your retirement years, Newport is definitely worth considering.

11. Portland

View of the Portland skyline from Pittock Acres Park, in Portland, Oregon

Okay, we had to do it. Let’s talk about Portland. Portland has a gigantic reputation as being both progressive and just plain strange but that doesn’t necessarily mean that it’s a bad retirement location.

So, here are my thoughts.

If you need the amenities that a large city offers, Portland is a decent choice.

The city is home to a number of excellent healthcare facilities, as well as a broad selection of housing options. And, with its close proximity to the ocean and the mountains, Portland offers retirees an abundance of opportunities for outdoor recreation.

However, hear me out, if you’re willing to spend the money required to settle down in Portland, strongly consider Seattle (or another large city in Washington) instead. They’re cleaner, safer, and overall just less “weird”.


Overall, I do think that Oregon is a great retirement destination if you can find a town where you fit in.

As with every place, you’ll want to visit and spend some time in a place before making any long-term decisions.

But then again, what do I know, I just live here. Maybe when I retire I’ll feel different and end up in Phoenix. But, somehow, I doubt it.