Taste Test

The Best Chocolate Chip-ish Cookies in Portland

From Toll House–inspired to smoky almond toffee to Ecuadoran bean-to-bar chocolate, we talked shop with some bakers and then tasted through the city’s best.

By Matthew Trueherz Photography by Michael Novak March 21, 2023

Image: Michael Novak

There are smart cookies and there are tough cookies. And of course there’s the Cookie Monster. “Cookie-cutter” has become an adjective, derived from the ruthless consistency cookies require, like tract homes, corporate franchises, and Marvel movies. But for many, there are really only chocolate chip cookies.  

It wasn’t until the 1930s that the American icon came into fashion. In 1938, Ruth Wakefield published a recipe for “chocolate crunch cookies” in her cookbook, Tried and True, a catalog of recipes served at her Toll House Restaurant in Whitman, Massachusetts. Betty Crocker was quick to feature the cookies on her influential cooking radio show, boosting it to fame. A year after the book published, Nestlé purchased the recipe and the Toll House name. 

The price of an icon? $1 and a lifetime supply of chocolate. (Inflation adjusted, that’s roughly 20 bucks and a lifetime supply of chocolate.)  

Today, chocolate chip cookies are as rooted in Americana as Levi’s and Coca-Cola. For bakers, they’re the ultimate tell. “Everyone’s calling card, I feel like, is their chocolate chip cookie,” says Siobhan Speirits, head baker and co-owner of Café Olli in Northeast Portland. “If you’re making a good chocolate chip cookie, it stands to reason that everything else you’re making is going to be just as good.” 

In one way or another, every chocolate chip cookie traces back to that storied touchstone: the Toll House chocolate chip cookie. Speirits calls it “everybody’s sort of introduction to a chocolate chip cookie.” 

But today, the Toll House cookie is more myth than concrete inspiration. Bakers magpie recipes and heirloom techniques centered around the idea of a chocolate chip cookie, developing their spin on Wakefield’s nostalgic combination of brown sugar and chocolate. They will tell you, repeatedly, that these tokens of collected wisdoms are simply “just a cookie.” They’re lying.  

Before opening Café Olli, Speirits baked—“Every. Single. Day.”—one of the most storied cookies in Portland, the much-celebrated Coquine cookie.  

With its distinctive smoky almond toffee, the vaunted Coquine cookie is far from your average chocolate chip. Coquine’s chef and co-owner, Katy Millard, came up with the recipe while consulting on the menu for a friend’s bar between jobs. In San Francisco, in 2009, Millard was thinking about bourbon: she grabbed for notes of vanilla, caramel, and something a bit savory and salty.  

“I had my Harold McGee book and I'm sitting there trying to tweak a cookie recipe at like, 1 in the morning while I'm working in the kitchen at this bar, you know?”  

What she landed on, Millard says, is “the most labor-intensive cookie on the planet.” Some highlights: dark, light brown, and white sugar; browned butter; organic flour sourced from a specific mill; California almonds, smoked in house, neatly halved, and crystallized in an amber toffee; the chocolate? “Guittard organic 66 percent wafers—the discs, not chips, ever.” 

Millard credits the success of her restaurant, cookies and otherwise, to this obsession with nailing the details. Nearly eight years in, she says they sell 300 cookies on a good Saturday. The restaurant also ships them nationwide—30 to 40 dozen a day around the holidays.  

“I didn’t ever think this would be on the menu at Coquine, ever,” says Millard. Coquine was going to be a serious restaurant; what place does a simple cookie have in that? But the cookie built its own cult following through a slew of pop-ups leading up to the restaurant’s opening. “There was so much hype around this silly cookie,” she says. (It’s not silly.) “It’s the monster that I have created. And it will be my lot in life to try and keep up with cookie production for decades to come.” 

Millard’s earliest chocolate chip cookie memory? Chips Ahoy at friends’ houses growing up. 

With some historical knowledge and priceless insights gleaned from experts, we set out to see what the rest of the town had to offer, cookie-wise. We asked around and put together a list of our edit staff’s picks. We convened—a full staff meeting. The agenda: to eat too many cookies. The rules: there are no rules. The criteria: deliciousness. We gathered around a jug of Oatly and got to work.  

Image: Michael Novak

Baker and Spice

whole wheat chocolate chip cookie  

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.” 

Image: Michael Novak

Lauretta Jean’s

“cowgirl cookie” 

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. 

Image: michael novak

Pizza Thief

“the closer” 

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. 

Image: michael novak


chocolate chip cookie  

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. 


Image: michael novak


chocolate chip cookie 

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. 


Image: michael novak


rocky road cookie

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.”  


Image: michael novak


chocolate chip cookie

“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. 


Image: michael novak

Café Olli

chocolate chip cookie 

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. 


Image: michael novak

Oui Presse

chocolate chip cookie

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. 


Image: michael novak


the Coquine cookie  

“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.” 


Image: michael novak

Editor's Pick!


chocolate chip cookie 

“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.