Every month, we dig through our restaurant listings to bring you a themed (and non-comprehensive!) roundup of places to eat out in Portland. Here, we highlight 12 spots that deserve every penny of your paycheck.

Castagna

A culinary poet and dessert artist, chef Justin Woodward splices seasonal high points, technical feats, and concentrated sauces into spare compositions of strange beauty. His best ideas are excitedly out of the box, among them an edible “terrarium” with dreamy onion custard and hypergreen onion-stalk purée standing in for soil beneath a greenhouse of backyard leaves and flowers. Meanwhile, veteran restaurateur Monique Siu keeps the modern machine humming behind the scenes. Woodward’s Michelin star–caliber desserts remain one of Portland’s best-kept secrets.

Clarklewis

White cloths now cover the tables, but this former warehouse restaurant maintains the original flavor of casual cool from its former era. Huge garage doors hang agape around the entire building, the smell of smoke pumps from the open wood-fired oven, and the menu juggles seasonal, contemporary American fare. It comes alive at lunch, when solid flavor profiles and the occasional out-of-the-park sandwich mingle with approachable ingredients attuned to the seasons. 

El Gaucho

The power players frolicking in this dimly lit, Sinatra-inspired dining room seem to revel in America’s tenuous, yet oddly optimistic, current economic condition. Perhaps they’re distracted by the high-quality dry-aged steaks, a fine Caesar salad, and a wickedly delicious bananas Foster (flambéed tableside) at prices in line with New York’s Delmonico’s. Still, El Gaucho has a soft spot for the budget diner, as witnessed by the crowd of la vie de bohème types happily cavorting in the bar at happy hour, where an Angus beef burger with a wedge salad sets you back only $22.

Farm Spirit

Chef Aaron Adams’s self-assured Buckman dining room boasts whimsical modernist vegan tasting menus and grand, self-imposed sourcing limits. (Nearly everything on the menu comes from less than 100 miles away.) Sit at his long chef’s counter, and his pure devotion to local fruits and vegetables shines. Carrots cook sous vide in their own sweet juices before getting seared black in cast iron, like steaks. Skinned, dehydrated tomatoes masquerade as strawberries, each a one-bite burst of late-summer salty sweetness. One dish holds the lilting sense memory of sitting in a grassy field as a kid; another tastes like clarified pond scum, little rounds of Swiss chard standing in for lily pads. Farm Spirit isn’t just “great for a vegan restaurant.” It’s great. Period. 

Hamlet (now closed)

Chef Cathy Whims’s Pearl District spot is less a bar and more of a food affair, swaddled in an eternal dusk of cushy leather banquettes and Portuguese-tiled walls. You’ll nibble warm, teeny olives and sip gin-melon cocktails, then leave perfumed with ham and sherry. The sexy-meets-geeky boîte is anchored by whole cured pig legs behind the counter that are worth more than a month’s rent. Grab a trio of Iowan La Quercia prosciuttos—sliced to whisper-thin ribbons—with a sherry-toting cocktail. Or, go luxe and experience the Spanish Iberico de Bellota ham, which morphs from salty to buttery to earthy to herby as the fat melts, like a gamey, umami-laden Everlasting Gobstopper. 

→  Hamlet’s Iberico de Bellota rings in at $19 per ounce.

Holdfast

Will Preisch and Joel Stocks deliver a fresh vision of what fine dining in Portland can be: high quality, highly personal, and casually ceremonial. The former pop-up relocated to its romantically rustic perch in the front room of Fausse Piste urban winery in 2015, where one dines among the barrels as electropop wafts from vintage speakers. But the wide-ranging thinkers still swing easily from modern to gritty, one-bite snacks to multifaceted entrées, foraged sea plants to beef snagged at New Seasons. Upgrades include coffee trays bearing homemade candies and lively juice pairings or complex ciders, wines, and craft brews. Sign up online, snuggle in at the chef’s counter, and dig into multiple courses conceived, cooked, composed, and hand-delivered by a pair of guys who also serve as the evening’s hosts and dishwashers. 

Langbaan

This cozy, cramped kitchen hidden in the back room of Thai restaurant PaaDee looks like a foodie’s vision of a Bangkok night market, with herbs everywhere, soup vapors billowing, and moody shadows creeping from table lamps. The décor only hints at what’s to come: a two-hour tasting menu of traditional Thai snacks, coconut-chunked soups, raw dishes, chile relishes, grilled pig parts, and some shockingly delightful desserts buried in salty coconut cream or infused with Thai candle smoke. At Akkapong “Earl” Ninsom’s restaurant there are no choices, no substitutions. Plunk down $65, settle in, and let the kitchen do the work. 

Laurelhurst Market

When Laurelhurst Market opened in 2009, it veered as far from Morton’s as you could get: affordable cuts, next-level sides, and a butcher counter to rival any in the city. Now in its middle-age, the indie steak house is still pure carnivore comfort, with rotating à la carte steaks, classic wedge salad, and potato-chip-topped mac and cheese. But chef Ben Bettinger has added rich, land-meets-ocean riffs, like creamy blood sausage tumbled with roasted beets in a tar-black swath of squid ink, as well as crunchy, craggy fried oysters over celery root and salty carpaccio. Salads, like a garlicky, creamy radicchio, weighted down with strips of grilled lamb heart, give Nostrana’s famed radicchio salad a run for its money.

Le Pigeon

Gabriel Rucker is a Portland original whose ideas crackle into something electric. Working off-the-cuff in his own world of complex flavor combinations, Rucker is possessed by French bistro cooking and Americana. Meat rules the ever-changing list—foie gras, pigeon, and pig parts are frequent guests. But salads can also be brilliant, and the French-focused wine list is deep, smart, and personal. The voltage extends to the softly lit, Parisian atmosphere, with communal tables and great energy. Le Pigeon embodies Portland’s rise on the national scene in a single, sharply focused snapshot.

→  At $205 for seven courses with ”reserve” wine pairings, Le Pigeon ranks among the priciest prix fixe meals in PDX.

Multnomah Whiskey Library

If Portland’s quirk mated with a 1920s speakeasy and a conspiracy theorist’s “smoke-filled room,” it might look a lot like the Multnomah Whiskey Library. At the top of a flight of stairs, a host asks for your name—yes, your full name—and your phone number. (They’ll call you when your table’s ready.) Somehow, such rituals feel refreshingly stuffy. Once inside there is cool, dark luxury, an academic devotion to liquor, and an unhurried, intimate atmosphere, complete with a massive fireplace and lawn jockeys. The drinks are superb and often mixed tableside: the house rye manhattan (easy to make, hard to make great) is a standout. Skip the food and delve into the Library’s 1,500-strong bottle roster. You might just find there’s a power broker hidden in your Portland soul after all. 

→  Want to make a reservation at this leather-clad whiskey club? Membership prices start at $600 annually.

Ox

Greg Denton and Gabrielle Quiñónez Denton’s meaty love story is told over flames erupting from a hand-cranked grill. Don’t miss their Uruguayan beef rib eye or the clam chowder, served with smoked bone marrow shouldering some fierce jalapeños. The intimate chef’s counter is an essential destination—and close enough to the wood fire to literally feel the heat. But happiness can be easily found at clustered tables or the teeny bar, home of a righteously twisted pisco sour: smoky and ear-tingling under a billowing white egg cloud. 

→  Sure, $115 seems like a lot for a bone-in rib eye, but Ox’s is 42 ounces—arguably enough to feed four or more.

Paley’s Place

In 1995, Kimberly and Vitaly Paley bailed from New York’s restaurant world for Portland, where they invested in farmers, not décor, and helped jump-start a new Northwest cuisine in a Victorian house perched over a nail salon. Over the years they’ve won a coveted James Beard Award, penned a coffee-table cookbook, and ushered in nightly packed houses for food that can be earthy, whimsical, or decadent. The kitchen still often juggles house classics—perfect Manila clams with chorizo, hand-cut fries, exquisite bone marrow towers knee-deep in red wine sauce and escargot—and mad creativity.

The Woodsman Tavern

Dark woods dominate the Woodsman Tavern, the first food project from Stumptown Coffee Roasters owner Duane Sorenson. Nothing screams Oregon more than the Woodsman’s seafood bar—a showcase of the freshest West Coast oysters and crabs around. Meats undergo a similarly rigorous screening process: the carefully assembled Country Ham plate, for example, is an exquisite bounty of porcine delights. The restaurant’s highbrow paper bucket of otherworldly, buttermilk-sopped fried chicken—fried hard in lard, aggressively herb-salted, and drizzled with honey—is clucking ecstasy.

→  The Woodsman’s two-tiered seafood tower—with oysters, crab, prawns, smoked mussels, and geoduck ceviche—will set you back $110.