The Sapphire Hotel— “Kimchilada” Aaron Lee

One of the best parts about living in a city with a small army of mixologists is getting to sample an array of cocktails that go far beyond what David Embury famously dubbed the “six basic drinks”: the daiquiri, Jack Rose, Manhattan, martini, old fashioned, and sidecar.

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This explosion in innovation has wandered into some particularly strange corners of the cocktail universe. Throughout Portland, some barkeeps aim to challenge the palates of their patrons, shaking and stirring together ingredients that on paper, might raise your eyebrows, but on your tongue will rouse your taste buds like never before.

Keep in mind: This is hardly a comprehensive list of oddball beverages. My selections simply represent my favorites right now; an account of boozy delights that I’ve enjoyed to date that will surely expand as I continue my slow bar crawl around the city. So what say you and I sidle up to the bar and get a little weird?

The Observatory/Over and Out— “Cumin Centipede”

The signature cocktail list at this Southeast restaurant and bar is larded with ingredients and infusions (habanero-infused rum??) that could—and maybe should—scare away your more traditional drinkers. For the rest of us, I suggest you dive right in, and start with a Cumin Centipede, which mixed cumin tequila with muddled cucumber, bell pepper, and cilantro. The finished product is something like sipping on alcohol-infused salsa verde.

The Sapphire Hotel— “Kimchilada”

If you’re slipping into this cozy spot for a woozy brunch, skip the Bloody Mary and Irish coffee and head straight for the Kimchilada. Served in a pint glass, this is an Asian-inspired take on the Michelada, using Kirin Ichiban beer from Japan and a healthy dose of tamari (basically a soy sauce alternative) and topped with a skewer of kimchi, the fermented vegetables that are a staple of Korean cuisine. And with its scoot of Haku vodka on the side, you can easily cleanse your palate to make every salty, bitter sip feel even more powerful.

Deadshot—“Clarified Milk Punch”

Deadshot—“Clarified Milk Punch”

By all rights, this should be on a brunch menu, if only to take advantage of an ingredient list that includes Cinnamon Toast Crunch and milk. It also has the nice astringent qualities that will take your eyes from half-lidded to wide awake. But its mix of rum, tequila, and sherry, shaken with pandan (fragrant plant used in Southeast Asian cuisine) and tea, renders the flavors closer to rice pudding. In other words, this is best taken as a digestif to close out a meal rather than to kick off the day.

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Botanist— “Jessica Rabbit” Kathleen Marie

Botanist— “Jessica Rabbit”

Like some of the best bars in the city, Botanist has a cocktail menu that changes with the seasons, meaning regular visits to this basement spot in the Pearl presents fresh opportunities for oddities like the Tequila Mockingbird, a fall drink made with tequila, white wine, and... beet ketchup. But don’t neglect the mainstays like the Jessica Rabbit, which brings together Singani 63, the sweet brandy-like spirit brought to the world by filmmaker Steven Soderbergh, treacle syrup, and—befitting the cocktail’s name—carrot butter. That last ingredient helps balance out the sweetness of the rest of the drink and adds a little poke of veggie flavor that will have you convinced that this concoction is somehow good for you.

Teardrop Lounge—“Belle Epoque”

I’ve got my work cut out for me when it comes to the cocktail menu of this downtown spot, as it’s teeming with irresistibly strange touches, from Thai chili and cinnamon tinctures to herbed fig-apple soda. To make sure they could handle the heavy stuff, I started with something somewhat simple but still unusual: the Belle Epoque. This sweet and tart rum drink is kept from the sugary brink by the use of a blood orange shrub (the vinegary tipple of many teetotalers) and lemon juice. But the crowning moment was when the bartender sprayed a housemade marshmallow with chartreuse-orange bitters and then gently charred it with a kitchen torch. It’s the perfect little detail that took this cocktail into the realm of the peculiar.

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