By Eliana Yoken ‘26

When school is feeling crumby, the best escape is a perfect chocolate chip cookie. So, I set out to find Portland’s best in this review, focusing on cookies within 15 minutes of the school, all recommended by students.

Chocolate chip cookies are easy to share and the perfect pick-me-up when you’re feeling down. As Gail Vance Civille, founder and president of Sensory Spectrum, a consulting firm that helps companies learn how sensory cues drive consumer perceptions of products, explains, “A chocolate chip cookie is a brilliant contrast among the flavors and among the textures.”

Taking into consideration all of the aspects that make chocolate chip cookies so delectable, I curated a set of criteria to help find the greatest. First, I reviewed the taste. I considered the sweet and buttery flavors that show up in cookies, searching for a balance.

Next, I identified the texture—chewy, crispy, soft, or dry. Then, I assessed the chocolate, thinking about the quality, amount, and spread. And, lastly, I asked myself, would I buy this again?

These four criteria helped me determine how many stars, out of five, each cookie would receive. So, grab a glass of milk and sip along as we discuss what the best cookie in PDX is.

Baker and Spice, Whole Wheat Chocolate Chip Cookie

Price: $2.50

*Baker and Spice cookie and entrance to the bakery. Courtesy of Eliana Yoken ‘26.*

Baker and Spice is a bakery I have grown up going to. From their delectable croissants to their freshly baked loaves of bread, there are plenty of outstanding bakes to try. Their chocolate chip cookie, however, is new to me and is also unique, as it is made using whole wheat flour.

First, I noticed its unique taste. The cookie isn’t overly sweet with a slight nutty flavor from the whole wheat flour. It is also very buttery, fulfilling all the desirable elements of a cookie.

The cookie’s texture is very chewy, with crispy-ish edges and a soft center. Crunchy Maldon flaky sea salt balances out the chewiness nicely. Texture-wise, I was very satisfied.

Its chocolate is perfectly distributed and semi-sweet—just how I like it. Plenty of chocolate chips in each bite, but not too overpowering.

Even though the whole wheat flavor gives off a healthier vibe, the price is low compared to other options and the flavor is good. The cookies’ size is relatively small, but I would purchase it time and time again for a quick, sweet and salty bite.

Word of advice: If you decide to go and taste this delectable cookie, I suggest you arrive at the bakery around its opening hours, as they often sell out of things quickly.

Final ranking: ⭐⭐⭐⭐

Grand Central Bakery, Chocolate Chip Cookie

Price: $2.95

*Grand Central Bakery cookie and counter at the bakery. Courtesy of Eliana Yoken ‘26.*

Next up, Grand Central Bakery, known, to me, for their delicious homemade breads. On their website, Grand Central Bakery describes their chocolate chip cookie as "a classic Tollhouse-style chocolate chip cookie," adding that it is “as good as it gets.”

When I picked up the cookie, it nearly broke in half, revealing its incredibly chewy texture. At first bite, it is very sweet, with no nutty or salty flavors and no crispiness anywhere to be found.

The chocolate chips are relatively lackluster and most likely semi-sweet. I found the cookie incredibly nostalgic. However, when sampling the cookie, Catlin Gabel School (CGS) student Hayley Schaaf ‘26 said it “tastes like a classic homemade cookie,” followed quickly, after some more bites by, "Good, but nothing special.”

Notably, you can purchase the cookie dough they use for their cookies and bring the ooey-gooey goodness back home with you.

Overall, yes, I would buy this enjoyable cookie again if I were looking for a familiar sweet treat. But I might not come to this bakery for their chocolate chip cookies alone.

Final ranking: ⭐⭐⭐

Ken’s Artisan Bakery, Valrhona Chocolate Chip Cookie

Price: $4.00

*Ken’s Artisan Bakery cookie and counter at the bakery. Courtesy of Eliana Yoken ‘26.*

Ken’s Artisan Bakery was bustling in its midday rush with rows of freshly baked bread, their massive cookies sitting at the front of the display case. There was an option to add in walnuts, but I declined to keep the review consistent.

The first bite of the cookie was surprisingly crispy. The edges were dark brown, and already, this cookie was by far the most cooked. The balance of the bitter, dark chocolate leveled out the buttery-sweet flavor of the rest of the cookie nicely.

As I got to the center of the cookie, I noticed the middle was softer. Additionally, I thought the ratio of large chocolate chips to the rest of the cookie was nice.

Nina Perov ‘28, CGS sophomore, suggested that the cookie was missing something that she “couldn’t quite name.” When she mentioned this, I also agreed. Perhaps sea salt would have been a nice additional crunch on top, or maybe the cookie was too crispy for my liking.

Regardless, the question still stands: would I actually buy this again? Yes, the cookie was very large and shareable. It was about the size of my open hand. However, its price is a bit daunting compared to others, and in my opinion, that lowers its rating.

Final ranking: ⭐⭐⭐

The Dragonfly Coffee House, Chocolate Chip Cookie

Price: $3.75

*The Dragonfly Coffee House cookie and entrance to the cafe. Courtesy of Eliana Yoken ‘26.*

There was an extreme downpour when I arrived at The Dragonfly. As I entered I was welcomed by the ambient lighting and the sweet smell of pastries. My eyes immediately met the glass case filled with pastries of all kinds, and there I saw the huge chocolate chip cookie.

The cookie appeared exceptionally well-cooked. Perfectly dark around the edges and lighter in the middle. When I picked it up and bit in, I found the same truth: it was crispy around the edges and chewy in the center.

The flavor was buttery and sweet, reminiscent of brown sugar. Each bite of the cookie is filled with sweet chocolate chips that balance out the buttery flavor nicely. The cookie was so good, I brought it to my sick friend, and she said it was so delicious, it made her day.

While eating the cookie, I thought to myself, "Would I buy this again?" And the answer came to me immediately. Yes, I would buy this cookie thousands of times.

Final ranking: ⭐⭐⭐⭐⭐

Final Verdict

After completing my search to find the best cookie, I have discovered that Portland has an exceptional variety of cookies. From small coffee houses to popular bakery chains, the options feel almost limitless.

The one that rose above the rest was The Dragonfly Coffee House's chocolate chip cookie, as it excelled in all criteria. It was so good that it received five stars, making it the best of the best.

If you want to conduct your own search for the best cookie in Portland, there are several bakeries I wasn’t able to get to, but were highly recommended by members of the CGS community. Cafe Olli, known for their chocolate chunk cookie, Cloudforest, which makes their own chocolate from scratch, and lastly, New Seasons Market, a simple yet classic cookie.

I hope these cookie recommendations help you survive the winter slump and start spring on a sweet note.

REVIEW: The quest for the ultimate ooey-gooey chocolate chip cookie