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For a long time, Daniel Shoemaker didn’t think of himself as a Pearl guy.
In 2006 Shoemaker came to Portland from San Francisco, where he’d worked for microbreweries for about 14 years, with the intention of opening a cocktail bar. He and his business partner, Ted Charak, considered various locations and settled on the Pearl for its central location and walkability.
Teardrop Lounge opened in July 2007, and it was already a conceptual gamble: Although Portland had a nascent craft cocktail scene, a lot of customers when asked what they liked to drink seemed to just answer, “Anything sweet.” “It felt a little bit like we were yanking people along,” Shoemaker says.
But sometime in 2009 or 2010, Shoemaker says, it was like a switch flipped. Customers started asking for drinks that weren’t too sweet. Other more cocktail-forward bars opened, and Teardrop was regularly written up in national outlets.
The Pearl was beginning to change, too. And while a lot of the places he loved have since closed, the neighborhood has managed to hang on to much of that early vibe.
“I came just after it started to transform,” he says. “It was still forming its identity, and a lot of that is still here. It’s still exactly that.”
1. Coffee Buzz
We start our walk with an iced coffee at Good Coffee (1114 NW Couch St., 971-282-3388, goodwith.us). When he first opened Teardrop, Shoemaker worked the late hours typical for nightlife but stepped away from service in 2014 to focus on his other business, the Commissary, a wholesaler of syrups and juices for bars. But the pandemic’s disruption put him back behind the bar. These days he typically works the beginning of service, when the bar opens at 4 pm. Now operating on an earlier schedule, he often starts his day at Good Coffee, which opened its Pearl District location in early 2024.
“I was so happy when these guys opened up,” Shoemaker says, though he’s also a fan of Barista, which has a location a few blocks away at NW 13th and Hoyt. “Nick and Sam [Purvis] are wonderful.” They’ve been friends and supporters of the Commissary, and place a high priority on great service, he notes.
“I’m a big believer that for us, for the bar, service is all that matters. Cocktails are a distant second,” Shoemaker says. And exceptional service, he adds, always flows from the ownership. “It’s engendered by the people that create and curate the space.”
2. It’s Lit
“It’s easy to take for granted that I’m two blocks away from one of the greatest bookstores on the planet,” Shoemaker says. “It’s the cardinal point of Portland in so many ways.”
He’s referring, of course, to Powell’s City of Books (1005 W Burnside St., 800-878-7323, powells.com). Once properly caffeinated, we head over to Powell’s and stroll through the Orange Room, where cookbooks (and cocktail books) are stored. I ask him what got him interested in cocktails after so many years working in breweries.
“I had tended bar for a long time, and in the worst decade. Some would say the ’70s would be worse, or the ’80s, but the ’90s were pretty awful,” at least in terms of cocktail culture, he says. “Most of us had a true love for the kitchen, but it never occurred to us that we could translate the same principles to the bar.”
While talking about the development of his palate as a bartender, Shoemaker eyes a copy of Susan Sontag’s Regarding the Pain of Others, picks it up and says he’s been meaning to get a copy. He’s not going to grab it today but is glad to know it’s there.
3. Paper Boat
We decide to head north and end up stopping in briefly at Oblation Papers & Press (516 NW 12th Ave., 503-223-1093, oblationpapers.com), a place Shoemaker says he spends far too much time in, buying “papers, journals, notebooks, stamp sets. It’s a fantastic place for gifts.”
Asked what he likes to read, Shoemaker rattles off a series of names, heavy on theorists (Roland Barthes, Walter Benjamin, Emmanuel Levinas). He’s also a big fan of the Argentinian short story writer, poet and essayist Jorge Luis Borges, and is currently reading Hermann Broch’s 1945 novel The Death of Virgil.
It turns out he has a bachelor’s degree in comparative literature from Stanford, where he studied English, French and Greek literature. And in the midst of reciting this list, he says he’s “in the midst of now stepping back and finally writing.” I ask if he feels comfortable talking about his writing. He demurs but does say he started writing 30 years ago, and has worked for decades with the hope of retiring early so he can fully dedicate himself to writing. The pandemic forced Teardrop to close for a year and freed up some time for him.
“My wife looked at me and said, ‘Guess you better get down and start writing,’” he says.
4. Hitting the Spot
It’s time for lunch, so we walk to Allora Italian Trattoria (504 NW 9th Ave., 503-445-4612, allorapdx.com). It turns out to be closed. (The place opens at 4 pm daily.) It opened in 2003 but remains a somewhat out-of-the-way spot. Shoemaker says he discovered it shortly after moving to Portland, when he lived near the Park Blocks. Originally conceived as simply a coffee and wine bar, it eventually became a full-service restaurant. (Current menu options include gnocchi di ricotta and spaghetti with handmade pork-and-beef meatballs.) Shoemaker describes owner Paolo Parrilli as “a really sweet guy” and praises the service offered here.
“It’s lovely service, always,” he says. “And it’s enough off the radar that it doesn’t track. A lot of people don’t know about it.”
Another favorite spot of Shoemaker’s, the Low Brow Lounge, is also closed during our walk. (“The fact that they’ve managed to remain an outlier in this neighborhood for so long is so impressive,” he says.) We end up at The Baker’s Mark (301 NW 10th Ave., thebakersmark.com), conveniently situated next door to Crybaby, Teardrop’s event space.
“I try not to go every day, but I go most days,” Shoemaker says. (His go-to order: the Godfather, a cold sub featuring genoa salami, prosciutto, capocollo, ham and mortadella.) “We’re so lucky they moved in right next door to where we are.” (The shop opened in early 2020; previously the storefront was occupied by a Ben & Jerry’s.)
Shoemaker may have chosen to set up shop in the Pearl purely for convenience, but his relationship with the neighborhood has shifted over the years. It feels like home now.
“I was talking to a friend of mine who lives in Ashland, and she said she couldn’t imagine living here. And I was like, ‘I could never do a small town where everybody knows you—you walk around and everyone knows your name,” he says. “And as we were having this conversation, walking around the Pearl, 15 different people said hi to me.”
DRINK: Teardrop Lounge, 1015 NW Everett St., 503-445-8109, teardroplounge.com, 4 pm–close daily.
