Given our proximity to one of the greatest wine regions in the world, it’s no wonder Portland sports as many killer wine bars as it does. But Bar Diane manages a difficult feat, working both as a casual neighborhood drinking spot and a vinophile’s destination. You can swing by for a cocktail and a lobster roll or plate of gnocchi at a bistro table, or you can sit at the marble bar and delve deep into the minutiae of the Oregon pinot noir or crémant d'Alsace in front of you. The versatility extends to the glass pours, from affordable table wines to splurgy champagne. Its charm is aided by the bright, cheerful decor with hand-painted walls that look like rings left over from glasses of rosé on a white tablecloth.

A sense of nostalgia permeates Clinton Street’s Dots Cafe, like someone forgot to tell the bartenders about the torments of the last decade. Here it’s still a halcyon 2010 or so, complete with post-ironic retro vibes: vinyl booths, white and black flocked wallpaper, a yard sale worth of velvet portraiture and animal art adorning the walls. You have to line up at the bar, but it gives you time to peruse the eclectic menu, cheesy fries and vegan burgers and quesadillas. A capable cocktail menu belies the bar’s age and maturity as it grows along with its clientele, though a shot and a local brew is still the best way to go. Summertime calls for lounging on its plaza seating and downing a serviceable glass of cheap rosé or a brain-aching slushy. It’s easy to relax here, to bask in the comforting glow of its colorful lanterns and feel like things might be okay, at least for now.

Not much has changed at this sultry den of indulgence in NE Portland since it opened in the summer of 2013. Candles drip from their stands along the bar, DJs spin records on the double turntable, and patrons devour wonton nachos and some of the city’s best cheeseburgers as soon as they hit the table. To go along with the astounding food menu is an audacious list of lush, vibrant cocktails that require at least a moment of careful consideration. You won’t find any “riffs on classics” here, just inventive concoctions more often stirred than shaken—this isn’t the bar for sours. Its permanence carries extra weight now as a testament to its founders, the late Naomi Pomeroy, and her husband, Kyle Linden Webster. When they built Expat it was like nowhere else in town, a dreamy fantasy evoking nineteenth-century escapes like Myanmar’s Pegu Club. Twelve years later it remains just as unique and just as intoxicating.

The concept of “tiki” is dicey. Its unseemly amalgamation of Polynesian and Southeast Asian cultures, too disconnected from reality to even be appropriative, raises the question: Is there even space for tiki today? Since 2012, Hale Pele has offered a compelling affirmative argument. There’s something unapologetically kitschy and charming about it, from the bartender pyrotechnics to the cheesy storm effects and thatch lanterns—it’s impossible not to have fun here. The drinks are bold and boozy, swimming with rums, fresh squeezed juices, and housemade syrups—never cloying or saccharine. Start with a mai tai or Singapore Sling before risking the flaming drinks and Zombies; then split some taro chips and crab Rangoon dip. Whatever you do, be sure to grab a ride share or bus home.

If you close your eyes and breathe deep on a quiet afternoon at the Horse Brass—before it’s invariably filled with regulars—you can get a whiff of cigarette smoke from decades past, forever remembered by the walls, wooden beams, and low ceilings. Half of those cigarettes were probably smoked by its late proprietor Don Younger, patron to the emergent brewing scene of the 1980s. Though Don has passed, the Brass feels time-locked, still strewn with vintage posters, maps, flags, dart boards, and the brass plaques that give the bar its name. A game of darts, with real, metal-headed projectiles, is still free. The extensive list of imported and local beers is still served by the proper 20-ounce pint. The menu has expanded beyond fish and chips and Scotch eggs, but those items remain. Most importantly, the bar continues Don’s dream of a heartfelt and loving homage to the pubs of the United Kingdom.

Even in the depths of Portland’s seemingly endless rainy season, Palomar feels like summer. One sip of a blended daiquiri will transport you to Miami or New Orleans, where bartender and founder Ricky Gomez cut his bartending teeth. Palomar shines by taking a distinct style of drinks—those blended daiquiris and piña coladas spotted in plastic cups on Bourbon Street—and marrying them to a modern cocktail sensibility, with serious rums, fresh citrus, and a measured amount of sugar. It’s like a grown-up party drink: all the fun, none of the sickly artificiality. Beyond these delightful concoctions, the bar enjoys playing with classics and adding something special, like an old-fashioned spruced up with overproof rum, coconut, and masala. For snacks, don’t skip the crispy, slightly sweet tostones with fry sauce.

Since 2011, co-owner and bartender Mike Shea has quietly influenced the city’s bar scene. Former bartenders talk about their time at Rum Club with the pride of a chef describing their stage at Noma, with alumni going on to open spots like Hey Love, Too Soon, and Tulip Shop Tavern. But legacy be damned—Rum Club is about the here and now, the kind of place you make the unwise, but ultimately memorable choice of “one last round.” Earlier in the evenings, it’s a place equally suited to after-work happy hour grousing and nervous first dates. Any lull of conversation is invariably filled by a discussion of everyone’s drink. Something rum-based is a good place to start, as simple as an old-fashioned or as complex as the Pedro Martinez, a house take on the father of the martini. By the second round of daiquiris, the bar overflows with off-work hospitality employees, rum geeks, and chatty regulars. By sundown, it’s a full-on rager most nights of the week. 

From its island on NE Sandy, the “Handy Slut” keeps a watchful eye over the rapidly changing urban landscape around it. Once, it stood prominently upon the intersection; today it is dwarfed by the surrounding apartment buildings. The bar itself isn’t immune to this change, having been cleaned up a bit over the years. But luckily, it hasn’t changed too much—the food’s a little better and the drinks a little pricier (like everywhere), but it presents that same charming familiarity. Regulars include parents stopping in for a drink after dropping their kids off at soccer practice, reminiscing on past visits over a pint and shot. Punks and hipsters shoot pool and play video poker, and the younger crowds close down the bar only to return hours later for a hangover-curing brunch. Portland may be growing up, but its youthful heart still sings at the Sandy Hut.

If the dark wood paneling and long marble bar tops don’t clue you into the deluxe voyage you’re about to embark on, the towering walls of spirits will. Elegant, sexy, drenched in class and rare whiskies, Scotch Lodge produces some of the most extraordinary drinks in Portland, and does so without a jigger of pretension. The Namesake encapsulates the experience: A lush, layered number, it hits with rich, dark cherry before the smoke drifts through from the scotch, a note of bitter Cynar and sweet vermouth playing in the background. It demands revisits, just like its eponymous bar. If all that weren’t enough to cement the Lodge’s position in Portland, it not-so-quietly rocks an incredible menu of bar food, with silky pasta dishes, Wagyu tartare, and ahi crudo. The fried brie sticks coated in pistachio and served with a verjus sauce contend for the greatest bar snack in the city.

In 2007, Daniel Shoemaker brought the Cocktail Renaissance to the Rose City when he opened Teardrop Lounge. Groundbreaking ideas included housemade bitters and syrups, infused spirits, and the use of vermouth in martinis, of all things. Twenty years later, and the bar has produced more talent than any other place in town, a veritable boot camp for cocktail bartenders. The cavernous dining room, built around the large central bar, is dark, loud, and a little dated to its mid-aughts origin with its monotone gray and glass. But it presents a distinct charm and directs focus to what matters most: what’s in the glass. While the space is rooted in time, the cocktail menu continues to evolve. It’s split into descriptive chapters: rich & robust, supple & herbal, arid & aromatic, etc. A brief, evocative description accompanies each drink, and a detailed glossary at the back guides neophytes and veterans alike through libation esoterica. If, somehow, nothing on the menu compels, the practiced bartenders clad in cocktail formal will have something in mind, and the moxie to execute it.

When it comes to cocktail bars in 2025 there are two paths: contemplative, earnest affairs where each drink commands undivided attention, and those unrestrained party spots where the cocktails are overshadowed by the wild and fun backdrops of a raucous night out. Too Soon manages to nail both approaches with a vibe that feels more SoHo than Kerns. Some come here just to sip super sparkly vodka sodas at the long, sleek, midcentury-style bar. Others opt for a bartender’s choice, perfectly crafted to the guest’s precise dimensions and preferences. During the summer, visitors pack the wooden patio for highballs and shrimp tacos; in the winter, they crowd into the long, narrow dining room, lingering until close when the kitchen sends out fresh baked cookies. Dark, chic, and sporty, it’s already a Portland mainstay less than two years after opening.