10 Best Places To Retire In Oregon For 2019

We analyzed over 38 places in Oregon to identify the ones that offer the most to retirees.

Editor’s Note: Data has been updated for 2019. This is our fourth time ranking the best places to retire in Oregon.

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When most people think of calling it quits on a career, they immediately think of a move to Florida.

But not not everyone wants to spend their golden years in Florida; some of us want to stay close to friends and family and within the great state of Oregon.

Where exactly in Oregon is the best place to retire? Well, there’s only one place to go for the answer — data — which returns Dallas as the best place to hang up your cleats.

To that end, we have tried to identify the places in Oregon that are safe, affordable, and have plenty of things to keep you busy well into retirement.

What did we find after pouring through all the data? Let’s just say we hope folks in Dallas don’t mind us spreading the word.

Why did Dallas take the top spot? And where are Portland and Salem?

Read on to see see all the golden parachute level details.

For Oregon state reading:

Dallas, OR

Overall SnackAbility


Population: 15,175
Rank Last Year: 43 (Up 42)
Median Rent: $715
Distance to Closest Airport: 57 miles
More on Dallas: Real Estate | Data | Photos

The city of Dallas is the county seat of Polk County, Oregon, United States. The population was 14,583 at the 2010 census.

Milwaukie, OR

Overall SnackAbility


Population: 20,643
Rank Last Year: 59 (Up 57)
Median Rent: $972
Distance to Closest Airport: 10 miles
More on Milwaukie: Real Estate | Data | Photos

Milwaukie is a city in Clackamas County, Oregon, United States. A very small portion of the city extends into Multnomah County. The population was 20,291 at the 2010 census. Founded in 1847 on the banks of the Willamette River, the city, known as the Dogwood City of the West, was incorporated in 1903 and is noted as the birthplace of the Bing cherry. The city is now a suburb of Portland and also adjoins the unincorporated areas of Clackamas and Oak Grove.

Review Of Milwaukie by HomeSnacks User

School system is fantastic and it is a really quiet pretty area south of Portland

Property values are much better than much of the Portland metro area.

The Dalles, OR

Overall SnackAbility


Population: 15,276
Rank Last Year: 45 (Up 42)
Median Rent: $757
Distance to Closest Airport: 69 miles
More on The Dalles: Real Estate | Data | Photos

The Dalles is the county seat and largest city of Wasco County, Oregon, United States. The population was 13,620 at the 2010 census, and is the largest city on the Oregon side along the Columbia River outside the Portland Metropolitan area.

Canby, OR

Source: Public domain
Overall SnackAbility


Population: 17,218
Rank Last Year: 47 (Up 43)
Median Rent: $935
Distance to Closest Airport: 22 miles
More on Canby: Real Estate | Data | Photos

Canby is a city in Clackamas County, Oregon, United States. The population was 15,829 at the 2010 census. It is along Oregon Route 99E, 2 miles northeast of Barlow. In May 2016 Canby was featured on ABC’s series 20/20, when the local “Canby Psychic” was part of an investigation of swindling a local rancher of $15 million.

Lake Oswego, OR

Overall SnackAbility


Population: 38,065
Rank Last Year: 71 (Up 66)
Median Rent: $1,371
Distance to Closest Airport: 13 miles
More on Lake Oswego: Real Estate | Data | Photos

Lake Oswego is a city in the State of Oregon, primarily in Clackamas County with small portions extending into neighboring Multnomah and Washington counties. Located about 8 miles south of Portland and surrounding the 405-acre Oswego Lake, the town was founded in 1847 and incorporated as Oswego in 1910. The city was the hub of Oregon’s brief iron industry in the late 19th century and is today an affluent suburb of Portland. As of the 2010 census, the city had a total population of 36,619, a 3.8% increase over the 2000 population of 35,278.

Roseburg, OR

Overall SnackAbility


Population: 22,201
Rank Last Year: 22 (Up 16)
Median Rent: $813
Distance to Closest Airport: 63 miles
More on Roseburg: Real Estate | Data | Photos

Roseburg is a city in the U.S. state of Oregon. It is located in the Umpqua River Valley in southern Oregon and is the county seat and most populous city of Douglas County. Founded 166years ago, in 1851, the population was 21,181 at the 2010 census, making it the principal city of the Roseburg, Oregon Micropolitan Statistical Area. The community developed along both sides of the South Umpqua River and is traversed by Interstate 5. Traditionally a lumber industry town, Roseburg is the home of Roseburg Forest Products.

Review Of Roseburg by HomeSnacks User

I live in Roseburg Oregon, which is one hour SOUTH of Eugene and we have a population of 21,549.

Pendleton, OR

Source: Public domain
Overall SnackAbility


Population: 16,861
Rank Last Year: 48 (Up 41)
Median Rent: $650
Distance to Closest Airport: 108 miles
More on Pendleton: Real Estate | Data | Photos

Pendleton is a city in Umatilla County, Oregon, United States. Developed along the Umatilla River, Pendleton was named in 1868 by the county commissioners for George H. Pendleton, Democratic candidate for vice-president in the 1864 presidential campaign. The population was 16,612 at the 2010 census, which includes approximately 1,600 inmates incarcerated at Eastern Oregon Correctional Institution. The city is the county seat of Umatilla County.

Gladstone, OR

Overall SnackAbility


Population: 11,850
Rank Last Year: 56 (Up 48)
Median Rent: $1,053
Distance to Closest Airport: 14 miles
More on Gladstone: Real Estate | Data | Photos

Gladstone is a city located in Clackamas County, Oregon, United States. The population was 11,491 at the 2010 census. Gladstone is an approximately 4-square-mile suburban community, 12 miles south of Portland, the largest city in Oregon, and located at the confluence of the Clackamas and Willamette rivers.

Grants Pass, OR

Overall SnackAbility


Population: 36,776
Rank Last Year: 17 (Up 8)
Median Rent: $859
Distance to Closest Airport: 23 miles
More on Grants Pass: Real Estate | Data | Photos

Grants Pass is a city in, and the county seat of, Josephine County, Oregon, United States. The city is located on Interstate 5, northwest of Medford. Attractions include the Rogue River, famous for its rafting, and the nearby Oregon Caves National Monument located 30 miles south of the city. Grants Pass is 256 miles south of Portland, the largest city in Oregon. The population was 34,533 at the 2010 census.

Review Of Grants Pass by HomeSnacks User

This is such a great little river town. The people are friendly and the climate is amazing. Not too terribly hot in the summer and the winters are mild. The rainfall is nice and the surrounding forest is green and beautiful. The schools are good, although most are quite old and need lots of repairs but the teachers are great.

Some of the best places to visit is the Rogue River for sure. There are rafting trips you can take. There are plenty of opportunities for fishing and the coast is only about 2 hours away if you want to go to the beach. The California Redwoods are nearby and the drive there is one of the most beautiful you will ever take.

Klamath Falls, OR

Overall SnackAbility


Population: 21,322
Rank Last Year: 2 (Down 8)
Median Rent: $719
Distance to Closest Airport: 57 miles
More on Klamath Falls: Real Estate | Data | Photos

Klamath Falls is a city in and the county seat of Klamath County, Oregon, United States. The city was originally called Linkville when George Nurse founded the town in 1867. It was named after the Link River, on whose falls the city was sited. The name was changed to Klamath Falls in 1893. The population was 20,840 at the 2010 census. The city is on the southeastern shore of the Upper Klamath Lake and about 25 miles north of the California-Oregon border.

How We Determined The Best Places To Retire In the Beaver State for 2019

To create our list of the best places in Oregon to retire, we first used Census data to find all places in the Beaver State — 372 cities and towns.

We then narrowed it down to places with at least 10,000 people that weren’t townships. This left us with 38 places from across the state.

For these 38, we looked at the following criteria taken from the Census, the FBI’s Crime Report, National Weather Service, and OpenFlights:

  • Low cost of living as measured by rent
  • Low crime
  • Things to do (Museums, Colleges, and Libraries in town)
  • Nice weather
  • Distance to the closest international airport
  • Other retirees (High median age)

We then ranked each of these places for each criteria from one to 38, with the lowest number being the best.

Finally, we took the average rank across these criteria. The place, in this case Dallas, with the lowest average rank was crowned the best of the best, a place for you to start your second careers.

Maybe You’re Not Ready To Retire In Oregon Yet…

So there you have it, the best place to retire in Oregon goes to Dallas.

If you’re not ready to hang up your office apparel yet, then these places might be up your alley:

  1. Eugene
  2. Redmond
  3. Springfield

For more Oregon reading, check out:

Where Are The Best Places To Retire In Oregon?

Rank City Population Median Rent
1 Dallas 15,175 $715
2 Milwaukie 20,643 $972
3 The Dalles 15,276 $757
4 Canby 17,218 $935
5 Lake Oswego 38,065 $1,371
6 Roseburg 22,201 $813
7 Pendleton 16,861 $650
8 Gladstone 11,850 $1,053
9 Grants Pass 36,776 $859
10 Klamath Falls 21,322 $719

About Chris Kolmar

Chris Kolmar has been in the real estate business for almost ten years now. He originally worked for Movoto Real Estate as the director of marketing before founding HomeSnacks.

He believes the key to finding the right place to live comes down to looking at the data, reading about things to do, and, most importantly, checking it out yourself before you move.

If you've been looking for a place to live in the past several years, you've probably stumbled upon his writing already.

You can find out more about him on LinkedIn or his website.