Everything marching out of this experimental modern kitchen during happy hour will make you smile. From the charm of icy tomato granita atop kusshi oysters to the whimsy of charred brussels sprout nachos and the cozy delight of applesauce-topped zucchini fritters, these thoughtfully playful, worldly dishes are designed to please. Best of all is the “slaw dog”—a house-smoked wiener beneath spicy slaw and a pickle spear, cut neatly in half to share. 5–7 p.m.
Nel Centro ($3–7)
You may have to invest a little time trolling the stylish bar, ready to pounce the moment a stool or table is abandoned—but believe us, it’s worth it. The reward holds full plates of fine-dining cuisine for fast-food prices: duck leg confit with lentils, deeply flavorful lamb meatballs, pizza piled with wild mushrooms and gorgonzola, and a messily wonderful lamb burger. Don’t be afraid to throw some elbows to snag your spot. 4–6 p.m.
3 Doors Down ($3–10)
This 18-year-old neighborhood Italian spot is the seasoned elder of our list—and with age, it seems, comes generosity. Heaping portions of fresh-made pasta (from tortiglioni in creamy, spicy vodka sauce to truffle oil–laced fettuccine) arrive perfectly al dente, along with gems like parmesan arancini, fried oysters, and a towering bibb lettuce salad. The best part? Every hour is happy hour at the bar. 5–9:30 p.m.
We’ve got three words for you: five dollar pizza. It’s hard to imagine a more pleasing nightcap than a well-blistered, full-size Italian-style margherita pizza, delivered piping hot for a five spot. Well, maybe throw in some smoky-sweet sliced pork belly, a glass of Chianti, and a tufted leather booth to curl up in. That might be even better. 9 p.m.–close
The best time for wallet watchers to feast on award-laden chef Cathy Whims’s food? Deep after dark. Sidle up to the bar from 9 p.m. on for a procession of Nostrana’s lovely charred Italian pizzas, the deservedly famous Insalata Nostrana (radicchio and rosemary-sage croutons coated in an addictive house-made Caesar), and a mac and cheese with five blended cheeses, tomatoes, and cream. It’s simplicity at its absolute best—and cheapest. 9 p.m.–close
There may be no cozier room in Portland than Savoy. If you can’t make out the proudly midwestern menu in the flickering candlelight, just trust us: order the chicken wings, slathered in chile vinaigrette; order the Supper Club sandwich, a serious specimen of comfort food; and by god, order the fried cheese curds. To drink? Why, a bottled and chilled manhattan fit for two, of course. 10 p.m.–close