Portland has been dubbed “where hipsters go to retire” and “where young people go to retire.” “Colin Meloy once heard it (Portland, Oregon—ed.) referred to as the place ‘where hipsters go to retire’” was cited in print in 2004.
 
The satirical sketch comedy television series Portlandia debuted in January 2011, but a music video,  Portlandia—Dream of the 90s, was released in December 2010. Lead actor Fred Armisen said:
 
“Portland is a city where young people go to retire.”
     
 
Wikipedia: Portlandia (TV series
Portlandia is a satirical sketch comedy television series, set and filmed in and around Portland, Oregon; it stars Carrie Brownstein (lead guitarist/singer for Wild Flag and Sleater-Kinney) and former Saturday Night Live cast member Fred Armisen. The show is produced by Andrew Singer, Lorne Michaels and David Allen Cress for Broadway Video Television and IFC Original Productions. It was created by Fred Armisen and Carrie Brownstein, along with Jonathan Krisel, who directs it. It debuted on the Independent Film Channel (IFC) on January 21, 2011. The series is currently in its fourth season and has been signed on for a fifth season. The show is scripted, but also heavily improvised.
   
Creative Loafing (Atlanta, GA)
June 10, 2004
Uncommon ground
The Shins and the Decemberists share a home, but not much more
By Nikhil Swaminathan
Colin Meloy once heard it referred to as the place “where hipsters go to retire.” It’s home to diverse bands such as Stephen Malkmus and the Jicks, the Shins, the Thermals, Sleater-Kinney, Quasi, the Standard and the Meloy-led Decemberists. While Seattle, Omaha, Minneapolis, Athens and Williamsburg are more familiar past and present epicenters of the musical underground, Portland quietly fosters a vibrant indie-pop scene.
     
Slate
SEPT. 11 2007 12:57 PM
The Indie City
Why Portland is America’s indie rock Mecca.
By Taylor Clark
(...)
They all just kind of live here. Which is why it’s often quipped that Portland is the place where hipsters go to retire.
 
YouTube
Portlandia - Dream of the 90s
dogsdoneit
Uploaded on Dec 17, 2010
Funny video about Portland, Oregon
(1:15—“Portland is a city where young people go to retire.”)
 
Twitter
Pete Stofle
‏@petestofle
“Portland - where young people go to retire” - thank you Portlandia, for that timeless line.  #in
9:34 PM - 21 Dec 2010
 
Twitter
Lindsay Selser
‏@lindsayselser
@EugeneSRTS “Portland, where the young go to retire”....bahahah
12:12 PM - 15 Jan 2011
 
Twitter
Eileen Rivera
‏@eileentv
“Portland, where the young go to retire” - ha! http://bit.ly/h5R5Z9 (via @GetGlue) #Portlandia
12:02 AM - 24 Jan 2011
 
Twitter
Jesse Felder
‏@jessefelder
Are you one of the millions of job seekers that recently gave up? Come to Portland where the young go to retire http://youtu.be/AVmq9dq6Nsg
4:13 PM - 4 Feb 2011
   
Statesman Journal (mid-Willamette Valley, OR)
Fame is fleeting but those awful freeze-ups live on
Carl Sampson Commentary 11:28 a.m. PST December 10, 2014
(...)
Fame is an interesting phenomenon. When someone is on TV or in the newspaper or online, they become famous. Because of that, you can pick them out of a crowd. In the case of Carrie Brownstein, I think the show she and Fred Armiston star in is a clever — and accurate — portrayal of Oregon’s Big City. They coined the phrase, “Portland: Where the young go to retire.”