A Completely Obsessive Ranking of Pepperidge Farm Cookies

Milano fans, take a deep breath...

Photo by Cole Saladino for Thrillist
Photo by Cole Saladino for Thrillist

When it comes to choosing favorite snacks, nostalgia is a key ingredient. But Pepperidge Farm's line of cookies, which have been around for more than 80 years now, do more than just conjure misty-eyed memories. They also teach you geography. Thanks to the Connecticut-based company—which is also behind non-cookie favorites like Goldfish crackers—you might have been inspired to look up Lisbon, Milano, and Lido, and learn. But which of their cookies tastes the best? To find out, our writer ripped open a bag of every single Pepperidge Farm cookie currently available.

Editor's note: For the purposes of this ranking, we obtained every single cookie available at the time of this publishing. Some seasonal favorites were unavailable at the time of testing. Pirouettes were not included, but remain delicious.
santa cruz oatmeal raisin cookies cookie
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49. Soft Baked Santa Cruz Oatmeal Raisin

The official cookie sponsor of retirement homes nationwide, the Santa Cruz is a little dense with a powerful cinnamon flavor, like a gingerbread cookie without the ginger. It's good, though it'd be even better if there were more oats and fewer raisins. Your grandmother might disagree... with everything, actually.

48. Tahoe Milk Chocolate Macadamia Nut

I mean, it’s still a shortbread cookie with chocolate, so that’s something. But there is a powerfully bitter artificial flavor here that I couldn’t shake. It's definitely not what comes to mind when I think of macadamia nuts.

47. Crunchy Almond Milano Slice

Dismissing the fact that the Milano Slice inherently confuses me (why would you only give us half a Milano?!), this cookie looks good enough with its smearing of almond-covered chocolate. Yet one bite revealed that same weird nut flavor as No. 48, which just makes me yearn for the OG Milano. And not half of one, either.

46. Pumpkin Spice Milano

The cookie itself is still good, but the flavor of the pumpkin spice amounts to nothing more than cinnamon and “orange dye” flavor, which spoils the poor Milano. Still, we're sure the pumpkin spice enthusiasts will love it!

45. Tahoe White Chocolate Macadamia Nut

Somehow this works a lot better than the milk chocolate chip version. Trying to get to the heart of the artificial nut flavor takes me to the bottom of the ingredient label, which reads, “Tree nut meal: almonds, cashews, pecans, walnut." But hey, those are all nuts, so... yeah.

44. S'mores Soft Baked

We’ve got your standard soft cookie here, which is pleasant and always fun to eat, but there’s no discernible flavor of s’mores to be found anywhere. The addition of graham cracker chunks into the cookie would send it over the edge. As it stands, these campfire dreams are dampened.

43. Raspberry Chocolate Milano

The raspberry is pretty off on this one. It tastes a bit like a cookie you'd eat to combat a sore throat.

42. Lido

These are pretty similar to the Lisbon—a hard, round cookie dipped in chocolate with even more chocolate baked in—only sans the extra chocolate. And the extra chocolate goes a long way.

41. Dulce De Leche Milano

Opening the bag brings on a powerful smell of caramel, but the taste isn't as rich as it lets on. It's kind of like a weak Werther’s cookie.

chessmen cookies cookie pepperidge farms
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40. Chessmen

Biting into one of these is akin to jumping off the high dive into a sea of butter. It’s the perfect flaky cookie to dip in tea on a rainy day. Crunchy, buttery, and iconic, they’d be downright incredible dipped in jam, too.

39. Soft Baked Sanibel Snickerdoodle

A big, chewy classic, the snickerdoodle here is very soft and amply coated in coarse sugar. The cinnamon quotient is a little low, though, which allows the butter flavor to take over. Still, sugar butter is delicious (see below).

38. Sugar

It’s a shortbread cookie covered in sugar. The only other flavor here is butter. Weirdly enough, the plainness of these translates to being able to eat way, way too many and not even realize it. They taste like Christmas.

bordeaux cookies pepperidge farms
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37. Bordeaux

A big, crispy cookie, the Bordeaux has a honey flavor to it rather than white sugar, which is appreciated among some of these more cloying, sugar-forward options.

36. Apricot Raspberry Thumbprint Cookies

More or less the same as the Strawberry Thumbprint (see below) but with a sweeter filling. The jam here is way less medicinal than it is in the Raspberry Milano, but still isn’t hitting the sharp notes that would elevate it to greatness.

35. Strawberry Thumbprint Cookies

A shortbread sandwich with a thin layer of strawberry jam smeared in between, this cookie reminds me of its British cousin the “jammy dodger,” which also sounds like an Edgar Wright movie. It could do with a bit more jam, though only if the jam was a bit tarter and not quite as sugary.

34. Farmhouse Thin & Crispy Triple Chocolate Chip

The image of the cookie this box is incredibly seductive, and my mouth starts instantly watering at the promise of lots and lots of chocolate. The cookie itself is a crumbly shortbread, and while it’s pretty buttery, the vanilla and sugar are the most dominant flavors here. I can barely tell it’s a chocolate cookie.

milano milk chocolate cookie milanos
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33. Milk Chocolate Milano

Fun fact! This time-honored classic was inspired by a trip to the Delacre Company in Brussels back in 1955. The cookies were so good that a deal was made to re-create them stateside, and the rest is history. True, this is the original incarnation of the Milano, but the original isn’t always the best—just look at The Dark Knight vs. Batman Begins. The chocolate here is a little skimpy, which leaves you with little more than a mouthful of plain cookie. They say it's the highest honor when a worthy successor surpasses the original. Such is the case with the Milano.

32. Orleans

Here we have a cookie that is more shortbread-y than thin and crispy. The mouthfeel of a sandwich cookie is always great, but there’s too little chocolate and little else going on here for it to merit much thought.

31. Candy Cane Milano

The aggressive red on the chocolate here is jarring. If you can move past that, these cookies smell like candy canes, which is delightful no matter what age you are. The flavor here is very subtle, less so than in other Pepperidge Farm mint cookies, but it’s enjoyable on the finish. 

30. Linzer Raspberry

A shortbread sandwich with a layer of jam in the middle, the cookie here is a bit more like a tea biscuit than a shortbread one (less crumble), but yay! The jam isn’t too sweet! Add in some dark chocolate and this would be a hell of a cookie. 

milano dark chocolate cookies
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29. Dark Chocolate Milano

In the Pepperidge Farm universe, dark chocolate reigns supreme. It’s deeper in flavor and makes for a more well-rounded cookie every time, but ultimately there isn’t as much as I’d like here.

28. Dark Chocolate Milano Minis

If Milanos were dangerous cookies to begin with, making them smaller and bite-sized is the most seductive trap I’ve ever willingly fallen into. There’s a nice, thick layer of chocolate proportionate to the cookie here, and the cookie size means I can put away a large volume of these before my boyfriend tears the bag away from me.

27. Sweet Toffee Milano Slices

This cookie is apparently what happens when a Heath Bar loves a Milano. Love is a beautiful thing. And in this case, the flaky bits of toffee combined with chocolate yield a flavor similar to a salted caramel mocha.

gingerman cookies ginger bread gingerbread
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26. Gingerman

It’s not your fault, Gingerman. You tried, but ultimately the pleasant holiday spice I knew you were capable of achieving (looking at you, Pumpkin Cheesecake) are surprisingly muted. The granulated sugar on top gives the cookie a fun texture, but it's more or less the only thing I can taste. Sorry little guy.

farmhouse milk chocolate chip cookies thin and crispy
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25. Farmhouse Thin & Crispy Milk Chocolate Chip

Same as the dark chocolate version, except not quite as good. Starting to see a pattern on the difference between dark and milk chocolate across the board here.

24. Chesapeake Dark Chocolate Pecan

At a cursory glance this seems decently saturated with chocolate. Despite this, my first and second bites of the crunchy, buttery cookie are criminally pecan-free. When the nuts are there, this is a banger. But when they're not, the nutless void is filled with longing.

23. Shortbread

This cookie looks a little bit like a seashell, with ridges protruding to give it an extra layer of textural dimension. They smell powerfully of brown butter, which makes my heart sing, and kind of taste like the butter & sugar sandwiches I made on toast as a (kind of weird) kid. They're chewy without being too flaky. I can even taste the addition of a little salt, which makes the whole, simple thing a lot better than expected.

22. Montauk Soft Baked Milk Chocolate

Soft cookies have the ability to render their harder brethren obsolete. The milk chocolate in these isn’t as tasty as the dark, but the soft cookie is much more balanced in flavor than the hard counterparts. That such a good cookie only comes in at 22 is a testament to the quality of the roster, and a harbinger of doom for my pancreas.

farmhouse dark chocolate chip thin crispy
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21. Farmhouse Thin & Crispy Dark Chocolate Chip

The thinness of the cookie gives it a nice snap, which is pretty satisfying. The cookie itself is very toffee- and butter-prominent, and the chunks are definitely all there. Dark chocolate is very clearly the way to go with the Thin & Crispy line.

20. Lemon Cookies

A basic shortbread cookie with a hint of tang. It’s got an irresistible citrus smell, but sadly the lemon flavor isn’t as strong as I had hoped for. Turned up to 11 and it'd be a top-10 contender.

19. Toasted Marshmallow Milano

Opening the bag instantly releases a cloud of marshmallow scent into your face, which is a great start. The taste of the marshmallow is pretty light though, only really coming in at the finish. It’s got more s’more soul to it than the Soft Baked S’mores brand: You can almost taste that campfire goodness throughout. 

18. Orange Chocolate Milano

This smells like those break-apart chocolate oranges that seem to only come around Christmas. If you like orange and chocolate as a pairing, you and this cookie will have a long, happy life together. Or a really short, happy one, depending on how hard you go on bags of cookies.

17. Pretzel Milano Slices

Crumbled pretzels laid onto a chocolate covered Milano slice makes for a great pairing—a little salt is a great way to bring out the flavor of chocolate. However, if promised a pretzel-topped cookie, I kind of want it to look like the floor at the Rold Gold factory.

caramel apple pie cookies cookie fall
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16. Caramel Apple Pie

A softie with plenty of chunks of caramel, there’s a slight hint of cinnamon going on here that screams fall. It’s a nice chewy cookie, but I wish the apples were a little more tart instead of sugary. 

15. Mint Chocolate Milano

The mint takes the classic Milano up a notch, and manages to temper the sweetness you usually get with mint cookies. It's kind of like a Thin Mint playing its farewell tour in Vegas.

14. Double Milk Chocolate Milano

The thick layer of chocolate sandwiched in the middle is a game changer—every Milano should have double the chocolate—but the milk chocolate version is just slightly less successful than the dark for reasons of personal bias and also the fact that it's true.

13. Mint Chocolate Milano Minis

This is the Mini-KISS equivalent of the regular Mint Chocolate Milano. And like Mini-Kiss, Milano Minis are way better than the full-sized version.

12. Lexington Milk Chocolate Toffee Almond

This shortbread cookie has a whole lot happening on the surface: think chocolate chunks, toffee, and almond pieces up top. It instantly disintegrates into your mouth on impact thanks to a ludicrous amount of butter barely held together with flour. A crispy cookie with addictively crispy bits, the toffee somehow helps the butter and almonds sync together in a perfect storm of sugary bliss.

tahiti coconut cookie cookies
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11. Tahiti Coconut

A shortbread sandwich with chocolate and coconut in the middle begging to be devoured. The coconut is a great addition that brightens up the whole thing and works well with its secret mistress, chocolate. Since there’s a whole lot of cookie at play here, a little more filling couldn’t hurt.

10. Lemon Milano

This pairing works surprisingly well. The lemon is definitely there, but isn’t overpowering, instead adding a refreshing element that cuts through the sugar nicely. I’m vaguely reminded of pie. That's always a good thing.

9. Lisbon

Snuck into the Chocolate Collection is the alluring Lisbon, a round, hard cookie dipped in chocolate with chocolate flecks baked in. It’s one of the best chocolate cookies Pepperidge Farm has to offer. Buttery cookie. Chocolate. Repeat. Probably too often.

nantucket dark chocolate double cookie pepperidge farms
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8. Nantucket Dark Chocolate

Like your one friend that went to Paris for a week, it’s got the slightest hint of extra sophistication owing to the inclusion of dark chocolate instead of milk. It’s a simple cookie that’s begging to be dipped in hot chocolate. Perhaps in that nice cafe your friend visited in Paris. 

7. Peppermint Milano Slices

There are no visible candy cane chunks, but these cookies do smell like the holidays. The peppermint jives incredibly well with the chocolate here. They keep each other in check without going overboard. The mint taste is subtle—it’s almost impossible to discern the difference between mint and peppermint—but damn, this is a great holiday cookie.

6. Double Dark Chocolate Milano

The extra chocolate makes a huge difference here: like a magical glass slipper, it takes the humble Milano and makes it downright regal. This is the platonic ideal of a Milano.

5. Pumpkin Cheesecake

This thing is surprisingly delicious, an instant holiday staple. It’s soft and chewy and tastes like a fall Yankee Candle smells. It’s also mercifully low on sugar, which lets the spices really shine through. I don’t know if you can distinctly taste a “cheesecake” flavor in the chunks (I tasted mostly white chocolate), but they’re incredibly satisfying when pitted against the spices in the cookie. I am keeping the empty bag as a reminder of the special memories we shared together.

4. Maui Chocolate Coconut Almond

This cookie is loaded in just the right places, with giant, massive chunks of chocolate and almond running through. The addition of the coconut is a blessing that lifts the whole thing higher than Johnny did Baby. It keeps everything from being too sweet and gives the whole thing a tropical feel. Balanced and loaded with fun textures in every bite, this cookie has it all: variety, size, and plenty of sugar.

brussels cookies
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3. Brussels

For some unknown reason Brussels were never stocked in my childhood cookie cabinet, so imagine my surprise when I bit into one and discovered that in the absence of nostalgia Pepperidge Farm can still create a really delicious snack. A layer of chocolate wedged between two shockingly thin, toffee-flavored cookies makes for a blessed union. If you’re into texture, this one’s for you.

captiva dark chococlate pepperidge farms cookies farm
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2. Soft Baked Captiva Dark Chocolate

This is it: A dark chocolate soft cookie with chocolate chunks. The secret is the cocoa in the cookie dough itself. You actually get the full richness of the chocolate in both the cookie and in the chunks without anything being too sweet. The chewy and chocolatey combo is just begging to be paired with a cold cup of milk or with a nice espresso. It’s a chocoholic’s dream, and the only reason it didn’t make it to the top is because it was only just usurped by the grand dame of Pepperidge Farm chocolate...

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1. Geneva

This chocolate, though.

Volume-wise there’s technically more chocolate in the Soft Baked Captiva. But the quality of the chocolate in the Geneva is something special. It’s fancy semi-sweet chocolate and is glossy like it’s been tempered, which is the mark of really good chocolate. The crispy cookie below is blissfully not marred by tons of sugar and butter, and had a nuttiness to it that makes the subtly prominent pecans sing. It is the culmination of all that is good in the Farm.

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Janelle Albukhari is a food writer and sugar addict who had to be lifted out of her house via helicopter following this article. Show her some love on Twitter @jenkhari.