You’ve done it now.
You stagger out of your favorite watering hole. While others make quick feet to their cars, you check your cell with a growing sense of dread. Yes, it’s after two, and depending on where you put up your feet, you might not be able to get home on TriMet for another three or four hours.
Some cities don’t sleep. Portland sorta dozes. Bustling intersections like Broadway and Burnside become empty and ghastly. Formerly familiar streets can take on a decidedly different character when lit by streetlamp and the only moving thing in blocks is a street sweeper. Chinatown is practically Escape from New York after 2 a.m. You don’t leave Chinatown so much as escape.
Don’t fret, though. There are still some places where you can spend the owlish hours in relative comfort and warmth.
The place to lay down your head
The Roxy, 1121 SW Stark St.
You can find yourself in a weird headspace at 3 a.m. Tiredness setting in, drunk wearing off, a lingering headache crawling around in your skull. For those who want to slump back and sit-out the midnight hours, this diner offers pleasantly dim booths set in corners, where you can order greasy American-traditional food under the warm polaroid smiles of Bill Clinton and John Lennon.
The place to hang out
The Southeast Grind Coffeehouse, 1223 SE Powell Blvd.
You might remember this place as the Fireside Coffee Lodge. It’s still around, under new management. The Southeast Grind is lit better than The Roxy, but the staff is every bit as pretentious. You’re more likely to find people reading or bathed in the glow of laptop screens than staring haggardly at the wall, too, which is a plus to a certain type of person, I suppose.
Their espresso is great.
The place to stretch your legs
The South Waterfront
Portland is a pretty friendly city compared to most, but I still wouldn’t want to be stuck out alone most of the time. If you’re itching to get out and walk off that last margarita, though, the South Waterfront has gorgeous views of the river at 3 a.m., and it’s much better lit than most districts.
The place to grub out
The Tik-Tok Diner, 11215 SE Division St. and 3330 SE 82nd Ave.
Need to get that boost of energy? The Tik-Tok has the best awful food (try the peanut butter pie) at a decent price. It’s open 24/7, and the service is excellent.