Day 1: Mississippi/North Portland – Grit & Gritty Pizza
Where the crust is thick, the beer is cheap, and the jukebox bleeds soul — Mississippi Ave is where Portland sheds its curated weirdness and gets genuinely scrappy.
Afternoon stroll down Mississippi Avenue: Locals here know it as the soul of North Portland—old storefronts, vinyl shops, indie cafés. Grab a coffee at a modest neighborhood café like Albina Press and wander the blocks where Portland’s hip indie community lives.
Dinner at Mississippi Pizza (pizza + music): Expect kid‑friendly crowds during early evening, a rotating DJ or live set—and thick, chewy pizza slices. Not designer‑hipster, just heartland warmth and rolling tunes. Families sit alongside the art‑crowd. Mississippi Pizza is not ‘cutting‑edge cuisine’—it’s comfort, music, molten cheese and people who know each other's names at the counter.
Ox: Honestly, we ate so many different parts of a pig….it’s how “whole hog” should be done. At Ox, the Argentine grill master's fiery passion is rivaled only by the heat of their chili.
Nightcap at a boiler‑room bar or brew‑pub: Skip the fancy Pearl — find a basement bar pouring stiff local IPA or cask beer. The kind of place where the bartender writes your name on a chalkboard and tosses you a pint with familiar timing.
Day 2: Southeast Division/Richmond – Food Cart Gems & Retro Coffee
In Portland, the best meals don’t come with a PR firm. They’re at carts where you none‑the‑wiser about Instagram, or in a haunted house turned coffee joint where people solve crossword puzzles over espresso in silence. You come for funeral potatoes in a food cart, stay for coffee in a haunted Victorian, and leave full of mole and questions about why every damn city isn’t this weird.
Lunch with locals at Ruthie’s food cart (Division & 36th): This food cart turns Mormon funeral‑potatoes nostalgia into modern comfort—rockfish sliders, biscuits with jams, quirky slaws. It’s cheap, weird, and diners line up because the food just works.
Afternoon espresso at Rimsky‑Korsakoffee House (Buckman): A haunted Craftsman house turned coffee lounge. They play classical music, serve hefty desserts, and locals meet over chessboards and strong brews in a wood‑paneled parlor.
Dinner at Kann (Ash St.): Kann was named the James Beard Foundation's Best New Restaurant in 2023. It was also recognized as one of Food & Wine's top 20 restaurants in the U.S. and ranked No. 1 on Esquire's best new restaurants in America list for 2022. You can land a table for 1 at the last minute, but otherwise, book it in advance.
Salt & Straw: It was born in Portland and is on the way to taking over the world. Try incredibly unique flavors like Arbequina Olive Oil, Pear & Blue Cheese, and Strawberry Honey Balsamic with Black Pepper.
Day 3: Central Eastside/Division – Creative Eats & Industrial Vibe
A warehouse brunch, chickpea nirvana, and curbside duck wraps — this is Portland doing fine dining with its sleeves rolled up and dirt under its fingernails.
Morning walk along Eastside industrial warehouses turned cafés: Rustic warehouses on the Willamette, coffee roasters and patios tucked between artisan studios. A place locals brunch on bánh mì or organic grains with reclaimed‑wood tables.
Lunch at Tusk or a food cart: Tusk is like Palm‑springs‑meets‑Portland in a bright Middle Eastern spot. Hummus so buttery it should be illegal, vegetables cooked like poetry, and overlooked by locals who know there’s no fuss, just balance. Alternatively, along Division or Central Eastside, you can find the locals stacking bowls: Khao Man Gai chicken cart, Cambodian Lao sandwiches, duck-filled jianbing. Portland’s food cart culture is a democratic buffet—no gating, just flavor.
Canard: It’s how Portland does french bar food, and it’s the new standard for happiness. Trust me - you’ll want to be there for happy hour (4-5pm) so you can fill-up on $4 Steam Burgers and some incredible drinks! Also, don’t leave without ordering the Foie Gras Dumplings.
Portland Bridge Scene: They may not be as famous as the connecting roads from rival pacific city, San Francisco, but PDX has nice, walkable bridges connecting east and west Portland. You can catch the Portland Stag Sign while traveling westbound on the Burnside Bridge.
Day 4: Northeast Alberta Arts & Cathedral Park – Family & Community
Morning at Peninsula Park Rose Garden / Cathedral Park: Cathedral Park under the St. Johns Bridge is quiet, full of locals and spectacular views. Nearby St. Johns Avenue has shops, cafes, and a mini‑golf/coffee spot called Wonderwood Springs.
Lunch on Alberta Avenue at Tin Shed Garden Café or Pizza Jerk: Tin Shed is big on daily family visits—they have dedicated kids menus, dog-friendly patios, and hearty scrambles or burgers. Pizza Jerk delivers throwback pies and soft-serve, lively wall art and friendly kids’ vibes.
Evening walk & dinner around Slabtown (NW Portland): This area is quietly evolving—industrial‑turned‑cozy spots like Besaws, Village Kitchen, friendly noodle stands. Expect locals unpacking vegetable‑heavy dinners over cheap wine.
Voodoo Doughnut: Once upon a time, Portland lacked donut shops until Kenneth “Cat Daddy” Pogson & Tres Shannon founded Voodoo Doughnut. The rest is history.
More Favorites
We’re dedicating this section to the work crowd. Who says corporate dinning needs to be stuffy and bland? Let loose and treat yourself to a proper meal at one or more of these Portland gems.
Luc Lac: Where the pho flows as freely as the late-night revelry, and your wallet leaves feeling lighter than the broth."
Top Burmese - Burma Joy: Joy is in the name, so why not? You’ll leave with the sweet scent of curry on your favorite shirt, but it’s delicious so (as the kids say), “worth it.” For more proof, the drinks are incredible, although I can’t remember their names for some reason.
Lechon: A porcine paradise, where they roast pigs with the kind of dedication usually reserved for competitive eating.
Q: It’s Portland's answer to 'cue, where the smoky goodness will have you singing! Yet, their veggie dishes are quite impressive, which is a rare feat.
