BEFORE WE GET into it, I want you to know I started this crawl with the best of intentions. It was innocent: I'd find one good drink, ask the person who made it where I should go next, and repeat. The only rule was that I had to go where I was told to go. I'm not a worst case-scenario type of guy, so I figured this would be a great idea.
I began with an old pal at Laurelhurst Market (3155 E Burnside), Stephen Dennis. I knew he'd graciously recommend a fellow bartender, and that he'd make me something delicious himself. His drink, called a Side Hug ($10), didn't disappoint. It's a summery little number starring local winemaker Pampleau's grapefruit aperitif, Punt e Mes, and Kina tonic syrup. Zesty and refreshing, it's as casual and light as its namesake half-embrace.
When I asked Stephen where to drink next, he pointed me toward La Moule (2500 SE Clinton). Specifically, to a drink called Lilah, an Oloroso sherry, bourbon, and green Chartreuse cocktail from one of La Moule's masterminds, Mark MacMinn. It's an exercise in checks and balances, with the Chartreuse and Oloroso playing on each other's complexity while the whiskey ensures things don't get too fancy.
MacMinn in turn suggested the Fino Countdown ($9) at Rum Club (720 SE Sandy), a sherry and blackstrap rum cocktail that ought to be on menus nationwide. (My companion ordered Pennies from Heaven [$9], which somehow manages to be a transcendent drink made from dry gin, Punt e Mes, Combier, and cacao liqueur.) It was at this point I realized this was becoming a sherry cocktail bar crawl—which isn't necessarily a bad thing—but I'd been hoping for a little more variety.
Careful what you wish for.
Turns out, Katie at Rum Club not only didn't recommend another sherry drink, she didn't send me after fancy cocktails at all. After some waffling, she set the night on an entirely new trajectory: "Oh! I think you should go get Jägerbombs at the Pitiful Princess" (12646 SE Division). She then proceeded to tell a story about a supposedly good time she had there doing just that. (I was and am suspicious.)
The Princess' Jägerbombs were predictably terrible—fluorescent blue with some kind of second- or third-string Red Bull backup. Our face must have betrayed our reluctant resignation, because the bartender looked at us like we were the most pitiful creatures in joint—and not even royalty, at that. I asked the dancer—who was obviously freezing cold, possibly dancing just to keep warm—where to go next, and she leaned close and whispered, "You should go to Spearmint Rhino," (15826 SE Division). "It's a better club."
I may never know if she was messing with me, or if she genuinely prefers the vibe of an international chain of vaguely safari-themed gentlemen's clubs, but as a stickler for the rules, I led the team further east.
And, okay, I don't know if Spearmint Rhino clubs are technically safari themed, but the carpet was leopard print, so you do the math. After a beer there (cold, satisfying), I decided it was okay to give the bartender one parameter when I asked her for our next stop: It had to be west.
"I'd go to Rachel's, and if Christina's working, tell her Julie says 'Hi.'" Rachel's Bar and Grill (12510 SE Division) is a cozy roadside dive with free pool, a friendly clientele, and a drink special called Liquid Marijuana ($6). Tacked to a shelf on the back wall was a sheet of printer paper with a marker-drawn ad listing the ingredients of this blue-green dream: Captain Morgan's, Malibu, blue curacao, Midori, pineapple, and sweet and sour. Maybe it tasted like what a 17-year-old thinks adult vacation tastes like, but to me it just tasted like drinking.
We played a few games of pool, then asked the bartender—not Christina, unfortunately—where to go. She said, "You should go to Laurelhurst Market and get a cocktail called a Side Hug."
No, not really. But I'd be lying if I said I wasn't holding out hope. Or at least a Kevin Bacon cameo in this game of Six Degrees. He directed us to "North Portland." The most specific advice we could squeeze out was from another guy on our side of the bar: "Oh, you should find a place up there. There's a bunch of great places."
That guy was a lifesaver. See, all roads may lead to Rachel's, but from there—thank God—they lead home.