The Portland Jazz Holiday has been celebrating jazz and the town of Portland, Oregon, featuring local and world performances, since 2004. Each Feb , the Holiday hosts ticketed performances, free shows, and jam sessions. PDX Jazz, the festival's umbrella organization, puts on diverse tutorial events, honoring both jazz and Black History Month.

The headliners for past Portland Jazz Holidays have included Wayne Shorter, McCoy Tyner, Dianne Reeves, Regina Carter, Charlie Haden, Patricia Hairdresser , Eddie Palmieri, Gary Burton, Poncho Sanchez, Nicholas Payton, Miguel Zenon, Luciana Souza, Danilo Perez, John Patitucci, and Joe Locke. There have also been lots of free performances, and the after-hours jam sessions are open to public collaboration.

Portland has had a prospering jazz scene since WW2, when thousands of Afro-American workers moved from the South to work in shipyards. When jazz started to grip the West Coast, the town was a stop for musicians traveling between two other jazz centers, Seattle, Washington and L. A., California.

Alaska Airlines reinvigorated the 2009 festival, which looked like it might be canceled in late 2008 when its largest sponsors pulled out because of the depression in the US. Its backing has carried thru the 2010 holiday.