Railside is one of those bars that almost feels like it doesn't belong to the rest of the city—seemingly placeless and timeless. But among the vast array of dive bars in Portland open early to the video poker set, Railside rewards travelers looking for a very specific type of vacation within the city. It's a beautiful sleeper of a dive bar with a patio looking out on the passing sleeper cars of nearby train tracks, with cheap-as-sin Buoy beer that's $3 at happy hour and a Camaro on jacks permanently pointed at the bar's patio like a drawing on a Pee Chee. A train will pass at least once, closer than you usually get to see them while holding a beer and eating surprisingly good $4 mini-corn dogs, maybe with one eye on the outdoor TV. There's also a mystery attached—an eight-foot-high Sears glamour portrait of a young woman taking up the window of the neighboring car lot above the basketball hoop, smiling forever at both the train rails and the Railside patio. The bartender doesn't know why she's there, but she's been there for years.
Happy hour: 4-6 pm Monday-Friday. $2 domestics, $2.50 wells, $3 craft beer.
Entertainment: Pool, video poker, TV.
5301 NE Portland Highway,503-282-8000. 10 am-1 am Monday-Thursday, 10 am-2 am Friday-Saturday, 10 am-10 pm Sunday.