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The Five-Point Weekend Escape Plan

Play in Portland’s Shadows

With its under-the-bridge skate parks, secretive supper clubs, and respectfully louche strip bars, the Northwest culture capital's darkest spots are also its coolest.


1. Where to Stay

Ace Hotel  

Relive the flophouse scene from Drugstore Cowboy (parts of which were filmed here in 1988) at the Ace Hotel (from $95), a newcomer to downtown’s Pearl District. Rooms are tiny but stylish with scratchy Pendleton Woolen Mills knits, murals by local street artists (Brent Wick’s giant cat room is a favorite), and iPod docks and turntables.

See Portland’s version of a rock-and-roll hotel—a mantle held by the Chateau in L.A. and the Chelsea in New York—at Jupiter (rooms from $114), a sixties roadside motel gone fastidiously mod. After catching an indie-rock show at the attached Doug Fir Lounge, join the after-party spilling over into the driveway.

For more peace and quiet, try the less cool but just as comfy McMenanins Kennedy School (from $99) in working-class Northeast Portland. On the site of a former elementary school, the property now includes adult pleasures like a soaking pool, a brew-n-view (i.e., a movie theater that serves beer), and a brewery.

Published on Oct 10, 2007 as a web exclusive.

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