Skip to main content
Remember the late-night home delivery cookie craze in which it suddenly seemed everyone wanted a hot cookie on their doorstep? Some would say the trend picked up in the 2010s with shops in Utah like Crumbl, while others credit Insomnia Cookies for stoking the late-night craving during the pandemic (though Seth Berkowitz founded the company way back in 2003).
All that aside, you might still find yourself with a hankering for a warm cookie at night brought right to you. But, what cookie will you pick?
A handful of Willamette Week staffers got together to taste test some of the city’s cookie shop offerings to determine which cookie(s) might be the tastiest. (In case you’re worried about tainted palates, don’t worry; they cleansed in between bites with Carr’s crackers.) Confession: These cookies aren’t all available quite as late as we’d like, so you might have to think ahead and order your cookies a little earlier in your eve (a reheat in the oven is advised).
Here’s what WWers had to say:
PDX Cookie Co.: The Best Taste
You read that right—the tastiest cookie lives in Montavilla. The company got its start in 2018 when owner and former bodybuilder Eva Smith wanted to make a post-show treat for competitors. A brick-and-mortar followed in 2020. PDX Cookie Co. (7919 SE Stark St., pdxcookieco.com; 4–10 pm daily) has a classic candy shop feel—walls painted a ’50s sky blue and nostalgic sweet smell hanging in the air. There’s also a subscription service, so you can get these cookies on a regular schedule.
WWers tried “Oreo Milkshake” ($5), a chocolate chip Oreo cookie with vanilla buttercream and crushed Oreo crumbs, a cousin to “Better Than S*x,” a blend that throws crushed Twix bars into the mix. It’s a dense thing, but the staff mostly concurred it was indeed the tastiest cookie (and a good looking one—cut slices looked almost like marbled granite). It’s gooey and “retains the dirtiness of an Oreo,” and like a good wine, the notes reveal themselves with each chew. Is it better than the number six though? We’ll save that pondering for late night.
Tasters’ notes:
“I would make out with this cookie at a bar but not take it home for the night.”
“It’s like raw cookie dough, but I love raw cookie dough.”
Insomnia Cookies: The Sweetest Flavor
The name and aim is clear: Insomnia Cookies (multiple locations, insomniacookies.com ; 11 am–1 am Monday–Wednesday, 11 am–3 am Thursday–Friday, noon–3 am Saturday, noon–1 am Sunday) is meant for late nights. The inside of its shops almost feels like a bedazzled Lyft meant for rides to and from the bar, and the smell of Insomnia Cookies is like if sugar could become a high frequency. That about sums up the taste too.
The sampled cookie was confetti deluxe ($4.99). More than one staffer specifically called out the flavor being a dead ringer for Safeway cookies. It’s sweet beyond sweet, like Cupcake wine, which could subjectively be a good or bad thing.
Tasters’ notes:
“A childhood birthday party nostalgia is quickly eclipsed by a looming feeling of dread.”
“I’ve been hit in the face with a fistful of candy.”
Sweet and Salty PDX: The Best Texture
If you’re casually mapping your way to the storefront for Sweet and Salty PDX (642 SE Stark St., sweetandsaltypdx.com; 10 am–9 pm Monday–Saturday), don’t be fooled by the blue building with the word “Cookies” painted in white letters a block away—that’s a weed chain. You want the actual corner shop, the one with mint green walls inside and Pearl Jam coming through the single speaker (like smoking weed in the ’90s). You’ll feel the warmth of cookies baking and of the shop owner Laura Brannan working the register. This spot just opened over the summer and claims to have the best cookies in Portland.
WWers tried the salted caramel chocolate cookie ($5), and the consensus was the feel of the cookie itself was excellent—“buoyant and chewy” and a “10 out of 10.” The taste was a bit of a tossup, with some loving the lavishiness of it and others feeling it was slightly out of balance. You’ve got to go try one yourself to decide who’s right.
Tasters’ notes:
“It’s rich but still playful.”
“If you’re gonna have a salted caramel cookie, I wanna taste some fucking salt. You’re reliant on a huge ass flake.”
Crumbl: The Worst Cookie
The Utah-born cookie franchise Crumbl (Multiple locations, crumblcookies.com. 8 am–10 pm Monday–Saturday) has a couple Portland locations that have the bright elastic sheen of being in the mall—the lights are cranked and the music is pop. We chose the double chocolate chip ($4.99), a standard treat topped with chocolate chunks that look almost geometric. The WW staff was less than thrilled—in fact, they were almost angry. The feedback ranged from “bland” to “strange and unimaginative” and “a disgusting monument to late-stage capitalism.” Dear reader, take your Lincoln elsewhere.
Tasters’ notes:
“It’s basically cookie dough that’s been taken to legally pasteurized.”
“It’s like AI tried to describe a chocolate chip cookie and it’s not quite there.”