Hood River, Oregon
Why hipsters love it: It's only an hour drive from hipster’s paradise (Portland!), and due to its rustic Columbia River Gorge locale, feels like it’s about million miles from anything. You honestly can’t swing a mustache around here without scoping another insane mountain top, valley, or waterfall view -- all of which you can hike, raft, or even snowboard (depending on the season) through.
Where to down all the craft beers: The beer literally flows like wine, because there are both breweries and wineries galore in this town. For local brews, start out at Big Horse Brew Pub and work your way through them all if you can (you probably can't). Or just visit during Hood River Hop Fest in September to sip more than 60 beers from 40 breweries.
Where to rock your skinny jeans (or pick up some new ones): Strolling Oak St, a thoroughfare that is packed full of arts & craft shops, bookstores, and contemporary galleries.