- Breakfast: By law, all Rose City eaters must check in at globe-trotting brunch czar Tasty n Sons. Order a bubbling cazuela of baked egg and red pepper Israeli shakshuka, and a Bloody Mary brandishing a house Slim Jim.
- Lunch: Will you go lemongrass-spiced game hen at Thai star Andy Ricker’s Pok Pok, or homey kuaytiaw pork gravy and rice-noodle comfort at his Sen Yai?
- Dinner: Luxuriate at Ken’s Artisan Pizza, home of giddy-making, char-blistered crusts.
- Post-dinner Drink: Cap the night with a textbook old-fashioned inside the 1,500-bottle-strong Multnomah Whiskey Library. Monday night is walk-ins only—which means you might actually snag a seat at a place usually hogged by reservations.
- Breakfast: Wake up with Pip’s Original’s fried-to-order, sea salt and honey-drizzled mini doughnuts, best nibbled with the café’s spice-walloped Ginger Rogers chai.
- Lunch: Grab a lunchtime table at Higgins’s bar and pay tribute to the charcuterie plate, loaded with silky herbed lardo and saucisson sec spiked with local grappa.
- Happy Hour: Cheer on two Top Chef contestants within a couple of downtown blocks: scarf down Doug Adams’s sly chicken-fried rabbit at Imperial, then marvel at Greg Gourdet’s happy hour at Departure, where pork belly with jalapeño-pickled cherries comes with a panoramic view.
- Dinner: Savor the bloody, beating heart of Portland’s food renaissance: Le Pigeon, where Gabriel Rucker wows neighbors and James Beard judges alike with wildly imaginative, no-holds-barred flavor assaults on the animal kingdom.
- Get Caffienated: Sip artful lattes at Sellwood’s adorable Scan-vintage coffee klatch Either/Or.
- Lunch: Chat up garrulous fromage master Steve Jones at Cheese Bar, where plates come loaded with gooey, nutty, stinky wonders paired with great Olympic Provisions sausages and stellar beers.
- Dinner: Hope you saved room—you’ll need your big-kid appetite for Naomi Pomeroy’s punk kingdom Beast, where coursed dinners celebrate Oregon’s bounty with meaty, gutsy flair.
- Post-dinner drink: Amble across the street, where Pomeroy teams up with husband Kyle Webster at the darkly cinematic Expatriate for perfectly balanced cocktails and chile-laced Southeast Asian salads and curries.
- Breakfast: There’s no finer oatmeal than the creamy steel-cut, fruit-laden bowl at twee-riffic brunch spot Sweedeedee.
- Coffee Break: Defeat your post-breakfast coma with a stiff “Jarbraltar” latte and obscure French cannelé at quirky downtown microroaster Courier Coffee.
- Lunch: Mosey two blocks south to worship at the altar of Nong’s Khao Man Gai—the rattletrap food cart where a single, habit-forming Thai dish of gingery simmered chicken serves as Portland’s culinary mascot.
- Dinner: A modest door hidden in the back of Southeast’s convivial Block & Tackle marks your dinner destination: a multicourse modernist seafood tour at Trent Pierce’s sleek speakeasy Roe.
- Breakfast: HA & VL’s rotating roster of clean, flavorful Vietnamese broths, floating everything from tender snails to shredded chicken, has garnered well-earned street cred.
- Lunch: Head for NoPo’s homey midday gem P’s & Q’s Market, where $8 lands you a smoky, barbecued riot of saucy brisket and cilantro-laced slaw on a cushy potato bun.
- Dinner: Supper is masterful salads and toothsome pastas at Ava Gene’s, where marbled Italy meets rock-’n’-roll Portland.
- Post-dinner Drink: Pop over to SE Wine Collective for a glass of pinot made on-site by industrious grape stompers, or sojourn to curio-cute Lauretta Jean’s, where flaky pies meet their match in clever cocktails.
- Breakfast: Skip the brunch lines and head to John Stewart’s modest sandwich shop Meat, Cheese, Bread for a perfect green chile–scramble breakfast burrito.
- Lunch: Wander northeast until you spy the SE 28th Avenue cart pod, where Burrasca slings soulful, handmade Florentine fare, Wolf & Bear’s hawks falafel slathered in addictive cilantro chile sauce, and Captured by Porches pours cult microbrews from a little bus.
- Dinner: All that street fare is a perfect counterpoint to a choreographed nine-course tasting menu at Castagna, where chef Justin Woodward morphs seasonal produce into brainy meditations on nature, as in his onion “terrarium” with green almonds and charcoal oil.
- Breakfast: At Kir Jensen’s Sugar Cube, citrusy cream-cheese frosting crowns unforgettable cinnamon rolls and tall savory strata arrive with equal parts technical precision and saucy swagger.
- Lunch: For a quick lunch, nab fresh corn tortillas filled with smoky-hot prawns or clove-rich barbacoa at the Ocean’s teeny house of Mexi-flavor, Uno Mas.
- Dinner: Line up by 4:30 p.m. for a seat at Greg and Gabrielle Denton’s wood-fired, chimichurri-fueled house of highbrow Argentine barbecue, Ox.
- Post-dinner Drink: Hope you’ve got energy for a final, late-night rejoinder at Barwares, Johanna Ware’s crimson-lit hideaway of cocktails and Asian mash-up eats.