1. The North(west) Pole at the Waiting Room
2327 NW Kearney St., 503-477-4380, thewaitingroompdx.com. 5-10 pm Friday-Saturday, through Dec. 21.
A blink-and-you'll-miss-it holiday pop-up, the North(west) Pole serves highbrow cocktails in the world's lowest-brow ski lodge. There's also six options for shot-skis—you know, that thing where four bros line up and down a shot off the deck of a downhill ski.
2. The Slammer
500 SE 8th Ave., 503-232-6504.
Lined with Christmas lights no matter the season, the festive Slammer Tavern is nearly the last divey survivor the gentrifying Buckman neighborhood will allow. Throw a song on the jukebox, order a cheap well whiskey, and play some skee-ball while your friends smoke outside.
3. Horse Brass Pub
4534 SE Belmont St., 503-232-2202, horsebrass.com.
A historical catalyst for Oregon's massive craft brew scene, this English-style pub often goes all in for the holidays, erecting a Christmas tree decorated with beer cans, cigarette boxes and bottles of HP Sauce.
Related: An Oral History of The Horse Brass.
4. The Standard
14 NE 22nd Ave., 503-233-4181.
The Standard is one of Portland's last true neighborhood bars, a ramshackle version of Penny Lane decorated in shattered CDs, corrugated metal and, during the holidays, plenty of Christmas kitsch. The bar was forced to end its $1 Hamm's special this year, but right now you can quaff seasonal brews for only $3.
5. The Palm Court at the Benson Hotel
309 SW Broadway, 503-228-2000, bensonhotel.com.
If you set foot in the lobby, you can easily imagine Manhattan's upper crust feeling right at home among the black-veined Circassian walnut walls and Austrian crystal chandeliers. The ground-floor lounge has a great happy hour, but the best reason for visiting is to gaze at another architectural wonder: elaborately designed Gingerbread Masterpiece that usually weighs more than 100 pounds and takes hundreds of hours to build.