Ranking 11 Flavors Of Pepperidge Farm's Milano Cookies

Pepperidge Farm was a real place, and it's where Margaret Rudkin started a baked goods empire in the 1930s. During a trip to Belgium, Rudkin became enamored with fancy chocolate cookies made for the royal family, and in 1955, Pepperidge Farm launched its Distinctive Cookies line, with its Eurocentric names such as Bordeaux, Biarritz, Capri, Brussels, Venice, and Dresden. A year later, the Naples cookie was born, where an open-faced cookie was covered with chocolate. After melty messes befell that cookie, a simple solution of adding a bookend cookie was implemented to preserve the chocolate longer. In 1957, that oval shaped cookie with a little bump on the outside — the Milano — was born.

In 1968, Pepperidge Farm introduced the first flavor variation with Mint joining the lineup. In the decades since, over 20 flavors have been offered up in those distinctive white bags, under its fashionable Italian name. Milano cookies have been named dropped in a song by RZA, and offered up on such shows as "Seinfeld," "Scrubs," "Lucifer," "Family Guy," and the series finale of "Frasier."

Today, there are plenty of Milano cookie flavors to choose from, but which one is truly the most distinctive, and which ones should be sent back to the farm? The Takeout took a bite of them all to see where the truth lies in this ultimate taste test and deliciously definitive ranking!

Recommendations are based on firsthand impressions of promotional materials and products provided by the manufacturer.

Fruits and chocolate have always been a hard pairing to make work, but strawberries and the brown confection have proved again and again to be a rare winning exception to the rule. Pepperidge Farm gave the flavor duo the room to work its magic within a Milano cookie, sometime around 2011. Fourteen years later, the combo made a comeback, but in lieu of dark chocolate, the strawberry flavoring was paired-up with the brand's new push for white chocolate flavors.

The bag of Strawberry White Chocolate Milano is topped and bottomed with a pleasant splash of darkened hot pink, and the ingredients label confirmed that the natural flavor of strawberry was indeed used in its making. Apparently that wasn't enough, as dehydrated raspberries had to come along for the ride to help define this cookie's taste.

Strawberry is often a flavor that sadly lends itself to pale imitations when infused into snack foods. The aroma of these were so artificial, and off-putting, I almost didn't want to put them in my mouth. Once I brought a single cookie to my nose, that noxious smell didn't really die down, which spelled further doom. Unfortunately, a taste of the actual cookie confirmed what my nose had warned me of — this does not work as a flavor worthy of the Milano name. If you happen to have a whole bag left to use, perhaps crumble them up and use them as a topper for a strawberry-themed ice cream cake.

For many, the question is often tea or coffee? The latter has lent its rich flavoring to ice creams and tiramisu. Tea, on the other hand, hasn't been so lucky to spread its flavors. Pepperidge Farm attempted to buck that norm with the London Fog Milano cookies, which debuted in 2025.

The London Fog Milano bag has a muted lavender color, with the image of a milky cuppa tea ready to be sipped. Opening the bag was almost like popping open a tea tin. Yes, Pepperidge Farm nailed the tea's essence, but has anyone ever asked for a cookie to smell or taste like one?

Alas, I gave it a fair shake, and while the cookie captured the tea's own distinctive flavor, my brain couldn't understand why it needed to be paired up with milk chocolate, and have a dash of vanilla extract added. A day later, I tried it again and began to appreciate it a bit more — more so for Pepperidge Farm taking the leap than for it being a flavor I'd want to try again. Not sure Earl Grey is the one tea to infuse its flavor into other things. I once had a Fog Nog Tea Latte from Starbucks Reserve, and it too tasted like a blasé bog. What about giving Lemon Ginger, Red Zinger, or how about Peppermint Milanos a go?

It's best not to go into any taste test with preconceived notions, but it's hard to bypass my prejudice where anything resembling the flavor of an orange gets intertwined with chocolate. This flavor combo once sounded exotic to me, but after trying orange Kit Kat bars ages ago, I have since retreated from it. Still, Orange Milanos with chocolate have been kicking around on shelves and apparently customers' homes since 1983, so its staying power has apparently proven its worth.

The flavor name is simply called "Orange Flavored Chocolate," but these Milanos don't appear to have any actual orange ingredients to the name. It's hard to separate the cookies to see the layers of chocolate and flavoring in between, but out of all the cookies, I really wanted to know what was inside. Nothing was physically orange to see here either, but both the dark chocolate layer, and the unknown, thinner white one on the opposite side both reeked of artificial orange flavoring.

Well, a funny thing happened on the way to dismissing them — they didn't taste all that bad. The orangeness was hyped up for the smell, but thankfully restrained for its actual flavoring. Thankfully the chocolate took the lead here, and allowed the orange to work a certain background citrus magic. Maybe it's time I rethink my sabbatical away from orange-chocolate products. Maybe.

For the longest time, the only straight chocolate Milano flavor was Dark Chocolate, and that didn't even need to spell that out on the bags. Milanos were just ... Milanos. Not sure what took Pepperidge Farm so long, but it finally hatched a Milk Chocolate version in 1994, necessitating a labeling difference that stands to this day. When these cookies launched, syndicated food review columnist Carolyn Wyman admitted, "The addition of milk chocolate transforms the Milano from a cookie of contrasting smooth and biting dark chocolate into one where the buttery cookie deliciously blends into a similarly smooth and creamy milk chocolate. It's different, but every bit as good as the original unless you prefer milk chocolate."

Decades later, Milk Chocolate Milanos are still with us, but its existence is less a revelation than just a fact of grocery store shelf life. They are straight-up nice solid, good old American chocolate cookies. There's nothing fancy about them, and they won't likely wow an eater who never encountered one. I guess if you were having a party and wanted to make sure your guests will enjoy cookies that are completely non-offensive, this is an easy option to exercise. The only problem with these is that I now know of a better version that exists, which some might say, is double the pleasure.

I have no deep memories that date back to childhood or an allegiance to Milano cookies, but I will admit that the signature flavor of the lineup has to belong to the one that started it all back in 1957. That Belgian dark chocolate taste that captured Pepperidge Farm's Margaret Rudkin's heart eons ago is still beating strong today. Prying open a bag (which can be tricky, if not done delicately), the contents have an amazingly rich chocolaty smell, like tearing into a bag of semi-sweet chocolate chips.

While this one is ranked one notch ahead of the Milk Chocolate Milanos, they are essentially on the same level. The question as to which one to buy over the other depends on your own personal chocolate preferences. I personally am more of a milk chocolate fan, but there's no denying that the richness of the semi-sweet chocolate here, budgeted between the dusty cookies remains a perennial winner. So why is this ranked so low then? Like the Milk Chocolate one, there's a far superior variation for the Dark Chocolate Milano that is twice as nice for the same exact price.

The White Chocolate Lemon Milano bag is beautiful, with an eye-catching bright yellow fading in a passive ombré with the white center label. The picture of a sliced lemon wedge dons the front, and the side notes that lemon oil, and turmeric extract for color, were included to add a bit of bona fides to the affair.

Lemon is another citrus fruit that can prove rather troublesome when applied to snacks, with the tendency to come off as being too artificial. The cookies certainly had a lemony smell, but it was more akin to those that perk up household cleaning products. The standard Milano cookie is a sandy brown color, and the pale yellow color that makes up this cookie's filling gives it an attractive look that helps to make it stand out. Splitting the cookies in two, I was kind of surprised to see a second, white filling layer that was sandwiched next to the yellow one.

This is another cookie where it has a strong aroma, but the flavoring is thankfully more subdued. The lemon isn't sour, puckery, nor overly sugary-sweet, and in turn it complements the cookie rather well. The White Chocolate Lemon Milanos reminded me a lot of the two citrusy-Girl Scout cookies with similar names and tastes, but somehow are two different entities — Lemonades and Lemon-Ups. If you're up for more lemon-flavored cookies when the Girl Scouts aren't peddling them around town, highly consider these ones from Pepperidge Farm.

Like its sister White Chocolate bags, the Coconut one also has a pleasing look to it, although the aqua green gets the bronze medal in my book. A slice of coconut appears on the package, and the ingredients to the side confirms it actually contains the natural flavoring of it, thanks to the inclusion of coconut distillate.

Breaking open the bag, I didn't really know what to expect, and the aroma that emanated out of it was one of the smoother smells out of all 11 flavors. For anyone who has ever had a coconut macaroon, this will be a real swell reminder. Like the Lemon Milano, the filling is a lighter and cooler hue than the others. Splitting the cookie apart, there appears to be two different layers with their own shades of white. One layer leans on the coconut flavoring, and the other the white chocolate.

Coconut is a very particular flavor, which in my opinion, is best used minimally. Pepperidge Farm must have kept that in mind when it crafted this one smart cookie. The coconut flavoring is ever present, but is handed-in at the right level. This gives one a taste of paradise, instead of knocking you over the head with a coconut falling from a palm tree. I'd actually love to see a milk or dark chocolate version to compete with the Girl Scouts' stellar Samoas.

If you've made it this far on this Milano ranking list you will have noticed I mentioned that the Milk Chocolate flavor is fine and dandy, but there's another option that easily eclipses it. Well, what if I told you there's a Milano that has Milk Chocolate and even more Milk Chocolate. After 23 years on shelves, Pepperidge Farm decided to up the ante of the Milk Chocolate Milano by introducing a "Double" version in 2017.

This is no sham, as the chocolate is doubled in every way imagined. The bag doesn't show two shavings of chocolate, but four. If you peer at the ingredients, instead of enriched wheat flour leading the call sheet, it's milk chocolate that gets the honors here. The aroma wafting from the bag smells twice, and perhaps even three times as chocolaty as its single counterpart does. Compare an actual Double Chocolate cookie to its forerunner single layer one and the proof is right there in the pudding, I mean, chocolate.

So what's the point of buying Milk Chocolate Milanos when you can have double the fun and double the yum? Sure, there's a bit more intake on the calories, fat, sodium, and carbs fronts, but none of these should matter when you're giving into such distinctive indulgences to begin with. You're worth it.

In 1993, Pepperidge Farm had twins, in the form of Double Dark Chocolate. Since there were no Milk Chocolate flavors at the time, it was originally known as Double Chocolate. Syndicated food critic Carolyn Wyman was smitten with the Double dealing ones, writing at the time, "I think most of us mortals are going to find eating just two of these new Milano cookies to be about as hard as eating just one Lay's potato chip." She added, "The dark chocolate layer is so thick that it snaps when you bite into it. In fact, the additional chocolate more or less shifts this Milano variety out of the simple cookie category and into that subset of treats that straddle the fence between cookie and candy."

Like with the Double Milk Chocolate, this bag doubles down on darkness, from the loose chunk pieces that appear on the front, semisweet chocolate running lead on the ingredient list, the smell working twice as hard in the bag, and the physical layered appearance and taste magnifying its magnificence times two. Who can say no to more chocolate? In fact, why stop here? I think we're ready for Triple Dark and Triple Milk Chocolate. What about a combo where dark and milk meld together in harmony, or better yet, a triple one that features both of those plus white chocolate? It can be called A Lot of Chocolates Milanos.

In a list of all time fruits, I personally wouldn't even place raspberries within the top 20. After the berry known as strawberry turned out to be a Milano flavor not worth picking, how could a raspberry flavor one fare any better? Well, this one, which has been growing on eaters since 2001, doesn't bother with white chocolate, but has been always paired with dark chocolate.

After taste testing several Milanos, I've learned that the smells escaping from the bag can be deceiving, so I tried not to judge the one that originated from the Raspberry Chocolate one. It mainly smelled like dark chocolate with an odd hint of raspberry. Examining the cookie, the thin layer of raspberry flavoring, which is made up of actual dehydrated raspberries, had a pretty purple coloring to it, which helped to make this cookie look like it was blushing.

The first bite was almost an epiphany. Not only was I surprised that such a flavor could work, but also at just how well it did. The raspberry flavoring alone is worth the price of admission, and it's almost too secondary to the smattering of solid dark chocolate included. I feel like this one could be even better if the ratio was flipped, where raspberry is the supreme filler over the chocolate. Regardless, this cookie is one I will surely remember going forward, and is a perfect one to serve for afternoon tea, or anytime really. Cheers.

In 1968, Milano branched out and finally introduced a follow-up flavor to join "plain" on shelves. To help kick off the publicity of this grand occasion, Pepperidge Farm even threw a high tea party for 175 editors at a media conference, where lucky eaters got to take some of the first public bites of Mint Milanos. Almost six decades on, Mint Chocolate Milanos are still minting money for the Pepperidge Farm brand.

To be honest, I am not sure I had ever had a Mint Chocolate Milano in my life before, and after having my first, I wondered how I lived a life without them for so long. I knew I was in for a literal treat when I split open the top of the bag, and an alluring scent of mint drew my nostrils in for some of the deepest breaths of this entire taste test. In a way, it almost worked the same kind of sinus magic that Vicks VapoRub does.

Infused with actual peppermint oil, these cookies quickly proved to be not only the perfect complement to Milano's standard dark chocolate, but stood as the ultimate Milano of them all. The mint is so refreshing and snappy that I almost couldn't resist downing the whole bag of them. They kind of reminded me of a reverse Thin Mint, where there was less of an emphasis on chocolate, and more on the mint. Turns out, that's what I've wanted all this time. I was so taken by this one flavor that I decided to freeze one of every Milano to see what the resulting taste would be. The only disappointing thing about Mint Chocolate Milanos is that a chilled one didn't seem to make this amazingly awesome cookie any more awesome.

The fine folks at Pepperidge Farm sent sample bags of 11 different Milano flavors for taste testing. The cookies were initially tasted in alphabetical order, and then tasted multiple times thereafter in no particular order.

The cookies were tasted by myself and two other eaters. While their opinions were noted, ultimately the final rankings were based on my personal tastes and experience with the cookies. The final criteria for this ranking included taste, texture, smell, deliciousness, uniqueness, overall lovability, and the likelihood I would buy a particular flavor over another. After a lot of cookie crumbling, Mint Chocolate proved itself the most worthy Milano of them all. Congrats! Stay cool.