This Southwest Portland bakery’s cookie appeared to be a promising start: balanced proportion of chocolate, an even light brown, solid height-to-width ratio. But a touch too sweet, says one editor. A touch too salty, says another. The whole-wheat flavor was a bit hard to place. “Better than a supermarket cookie,” offers art director Mike Novak, noting the pronounced chocolate flavor. “I feel like I just had a sandwich and chips,” says digital engagement editor Dalila Brent. “And now I’m eating the cookie that came with.” 

This twist on the oat, pecan, and coconut-enriched classic (Lauretta Jean’s adds dried blueberries and cornflakes to what’s known as a “cowboy” cookie) was unfortunately a bit pale. Food editor Katherine Chew Hamilton notes the texture is fun to chew, but we were left wanting a bit more toasty flavor. 

It’s not every pizza shop that gets recognized for a cookie. “The closer” is sold as a “¼ lb triple chocolate hazelnut cookie.” And it is huge, as promised—the biggest of the day. It’s always a good sign when the weight of a cookie is advertised. Restaurant critic Karen Brooks suspects there may be bits of Heath Bar mixed into the dough. One thing’s for sure: there’re plenty of hazelnuts. Overall, it’s a solid cookie, but the consensus is that the filbert comes through a bit strong. 

Courier is less a bakery and more a coffee shop that took it upon itself to put some pastries in the window, which is really the charm of the place. The cookies are very much homestyle, topped lightly with flaky sea salt before being baked in a little convection oven under the counter. Such a system has its ebbs and flows, but the high points are unmatched, notes Brooks, a devout champion of Courier’s cookies. The day of our tasting, the cookies were a bit inconsistent: some doughy, while others were a bit too crisp—delicious, but Brooks mentions they’re a bit off their game. That said, we’re not writing them off anytime soon. 

Veteran Portland baker Kim Boyce’s shop works mostly as a wholesaler these days, outfitting coffee houses around town like Upper Left Roasters, Prince Coffee, Barista, Deadstock, and Less and More. You can, however, snag some cookies and the like from the NE Sandy storefront on weekend mornings. This cookie leans slightly crumbly, with cracks across the top hinting at its slightly sandy texture. It’s a bit compact, with a decent heft. Managing editor Margaret Seiler notes a distinct wheatiness. Novak is sold on the layered chocolate laced throughout: “strata,” he calls it. 

Seiler gets out a ruler to measure this sizable cookie: 4 ½ inches in diameter. Visible from the top are large chunks of light and dark chocolate, pecans, and a few toasted mini marshmallows. Brooks calls it a “candy bar cookie.” The texture is flawless—pleasantly gooey with a nice crumb—we expected nothing less from the makers of our favorite chocolate croissant in town. But the long ingredient list, one editor notes, is “almost too much.”  

“Look at that!” says Hamilton. “It’s like a chocolate bar in there.” When Keeper moved to its current Creston-Kenilworth location, a rambling old stucco building with countless reading nooks and “Keeper” tiled into the floor, it gained substantial baking space. That elbow room shows in the cookies. They’re big, spread wide, and toasted to a rich brown color. It checks all the boxes, says one editor: “chewy, large, tasty.” They’re coloring inside the lines here, and it’s working. 

With its heavy dose of flake salt on top and pleasant kick of bitter, dark chocolate, one editor notes this cookie would be great with a cup of coffee. “Fruity!” Hamilton points out about the fancy chocolate. The cookie has a nice crisp exterior but doesn’t sacrifice a soft chew in the middle. We’re on board with this one; it has one foot in the Toll House camp and the other in the dressed-up cookie camp. 

This sleepy SE Hawthorne coffee shop is known for its hazelnut Bundt coffee cake, but these unassuming cookies are on the same level. “Beautifully baked,” says Novak. “Textbook; an argument for not having to overdo it.” Seiler concurs: “The quintessential cookie.” They’re salty but not too much so, and the semisweet chocolate is a surprisingly nice touch. The edges are crisp, “like they’re fried in butter,” adds Hamilton. And the center is tender and chewy. A strong contender, especially for a cookie holding so close to tradition. 

“Not a classic taste,” notes one editor. “And that’s good!” Seiler is impressed with the proportions. “Almost an inch high!” she says, ruler in hand (7/8 inches, to be exact; 3 inches in diameter). This cookie’s smoked-almond-toffee reputation precedes it, and it delivers on the hype. The subtle smoke isn’t for everyone: “Definitely doesn’t hit the usual chocolate chip cookie notes,” says Hamilton. But it takes some ingenuity to stand out in a sea of cookies. “When you look at something after you take a bite of it,” Brent says, eyes locked on the cookie in her hand, “you know it’s good.” 

“We have now just—” Brooks starts, before losing her words to the cookie. “Now we’re talking,” she says, chewing a gooey bite. Another editor notes the cookie’s delicate shine, breaking it open to expose its brownie-like center. Cloudforest is a bean-to-bar chocolate producer that also sells a few pastries at its minimal, SE Hawthorne café, alongside a very grown-up hot chocolate. By a long shot, this was the most aromatic cookie of the day, emitting an intoxicating, fruit-forward chocolate aroma with a boozy kick of its own carefully sourced Ecuadoran vanilla. “House-made chocolate and vanilla, who does this?” says Brooks. Several staffers ask for the café’s address.