Tastes Like Luck: Chocolate Shamrock Sandwich Cookies

Chocolate Shamrocks

Got luck?

I love shamrocks. They make me happy– any time of year, really. The symbol of the shamrock is of course associated with Ireland today, and has come to be synonymous with St. Patrick’s Day. The word comes from the Irish-Gaelic seamróg, meaning “little clover”. Legend has it that St. Patrick used this 3-leaf clover to illustrate the Holy Trinity when bringing Christianity to the pagan Celts of the Emerald Isle in the 5th Century. However, the shamrock was significant long before St. Patrick; the Druids used it for medicinal purposes, and they believed that this common, native Irish plant was sacred. Many ancient Celtic symbols feature the number 3, such as the Breton triskèle and the triquetra, as this number was thought to hold mystical powers. Many of these symbols pre-date Christianity, depicting elements of nature, rather than religion. On occasion, a 4-leaf clover can be found among its 3-leaf siblings, which is said to bring extra luck. In the 18th Century, the shamrock became a symbol of rebellion, as the Irish fought numerous rivals attempting to invade the island; this period spawned the expression “wearing o’ the green” as a sign of Irish national pride. Since then, it has grown in popularity to represent Ireland in government, songs, poetry, and as a decorative motif in arts, architecture, jewelry… and of course baked goods. 🙂

Chocolate Shamrocks 14

I also love me some chocolate sandwich cookies. And Bailey’s Irish Cream. And caramel. When pondering baking projects for March, it became clear to me that these three elements were destined to come together with the shamrock into some kind of St. Patrick’s Day baked goodness. I guess chocolate, caramel, and Bailey’s are my own special baking trinity! Enter: Salt & Pepper Sandwich Cookies from Baked Explorations. I made Malted Milk Sandwich Cookies last week, which are divine, and these two cookie recipes from BAKED use the same vanilla creme filling, so obviously I had to make the chocolate sandwich cookies too; they just go together. The chocolate cookie dough is an homage to the classic Oreo, which happens to be one of my favorite things on this planet; I would eat Oreos for breakfast, lunch, and dinner if it was socially acceptable. I had made these cookies once before and they were delightful. Not quite as dark as real Oreos, but they’re not necessarily meant to be. The hint of white pepper in the dough and a sprinkling of fleur de sel (hand-harvested French sea salt) is a fun and sophisticated twist. This was unquestionably my go-to chocolate cookie dough for the shamrocks, though I made some slight modifications to the recipe.

Chocolate Sandwich Cookies

First, I decided to omit the lovely salt and pepper. While I was reluctant to do this, I wasn’t sure how much they would compete with or complement the added flavors of Bailey’s, whiskey, and caramel. Second, I substituted half of the dark cocoa powder with black cocoa to make them even darker and more like Oreos. (If you don’t have this on hand, just use all dark cocoa powder.) Black cocoa is over-roasted to achieve an almost black color and a deeeeeep flavor. It’s difficult to find in the grocery store, but you can order it online (I recommend Guittard or King Arthur Flour). Both changes were successful, and the cookies oozed with chocolaty, caramel-y, creamy, boozy flavors!

The filling also resembles that of Oreos, sans a whole lot of chemicals (though I’m not crazy about using so much vegetable shortening). Said filling conveniently contains a small amount of rum, which could easily be swapped for Irish Cream; my vision was coming together nicely! Finally, I remembered that I had recently made a batch of Whiskey Caramel Sauce for a different BAKED recipe, and given that these cookies were for St. Patrick’s Day, I figured, the more liqueur, the merrier! Needless to say, I recommend using a good Irish whiskey for this fine occasion. I happened to use Bushmills, but I know there are many heated debates about the merits of Bushmills vs. Jameson– you decide. 😉

I made some regular round cookies in addition to the shamrocks, and I did sprinkle the fleur de sel on those– the contrast of sweet and salty really puts these pretty little sandwiches over the top. (I included the salt and pepper in the ingredient list, but I recommend omitting them for the Irish adaptation.) It’s hard to say which version I like better, though certainly the Irish cookies are more festive! If I’m being honest, my preference here is two-fisting: a chocolate cookie in one hand, and a malted cookie in the other! If you want to experience this amazingness, make both the chocolate and malted doughs and a double batch of filling– you’ll be glad you did!

Chocolate Shamrocks 2

Chocolate Shamrock Sandwich Cookies
Adapted from Baked Explorations
Makes about 30 cookie sandwiches

  • 3 ½ cups all-purpose flour
  • ¾ teaspoon kosher salt
  • ¼ teaspoon fleur de sel, plus more for decorating (omit decoration for Irish version)
  • 2 teaspoons white pepper (omit for Irish version)
  • 2 tablespoons dark unsweetened cocoa powder, such as Valrhona
  • 2 tablespoons black cocoa powder
  • 1 ½ cups (3 sticks) unsalted butter, cut into 1-inch cubes, cool but not cold
  • 1 ¼ cups granulated sugar
  • 1 ¾ cups confectioners’ sugar
  • 3 large egg yolks
  • 1 tablespoon pure vanilla extract
  • 3 ounces good quality dark chocolate (60 to 72%), melted & cooled slightly

Whisk together the flour, salt, fleur de sel, and both cocoa powders in a large bowl, breaking up any large chunks of cocoa. (If using the white pepper, add this now as well.) Sift the mixture onto a sheet of wax paper on your countertop. Sift a second time back into the bowl and set aside.

Chocolate Shamrocks 3

Place the butter and both sugars in the bowl of a stand mixer fitted with the paddle attachment. Beat together on medium speed until the mixture is light and fluffy, about 3 minutes. Scrape down the sides of the bowl. Add the egg yolks, one at a time, beating after each addition until incorporated. Add the vanilla extract and the melted chocolate and beat until the batter is a homogenous light brown. Scrape down the bowl, including the bottom, and give the mixture another quick whirl to make sure everything is evenly mixed.

Chocolate Shamrocks 10

Add half of the flour/cocoa mixture and beat just until incorporated. Scrape down the bowl and add the second half of the dry ingredients. Mix just until the flour is absorbed.

Loosely shape the dough into four balls. Flatten them into disks and wrap each one tightly in plastic wrap. Chill the dough disks in the fridge for at least 3 hours, or store in the freezer for future use.

When you’re ready to roll out the dough, take the disks out of the refrigerator and let them warm up a bit at room temperature. The dough will be very solid straight out of the fridge. (I let mine sit out for about 30 minutes.) Preheat the oven to 350°F and position a baking rack in the center. Line two rimless cookie sheets with parchment paper. I prefer to bake my cookies one sheet at a time, but you can bake both together by positioning two racks in the upper and lower positions.

Generously flour your work surface and rolling pin, as this dough will get sticky when it warms up. Unwrap one disk and gently knead the dough in your hands until pliable. Place it on your work surface and roll the dough out to about ¼-inch thick. Rotate the dough round after every few rolls to prevent sticking. Flour the work surface and rolling pin as needed (though too much flour may leave white streaks on your cookie cutouts). To make the shamrocks, cut your shapes using a shamrock cookie cutter (mine is about 2 ½ inches).

Chocolate Shamrocks 4

If making traditional round cookies, use a plain or fluted cutter of any diameter you like. These cookies lend well to different sizes, so feel free to make anything from palm-sized cookies to tiny cookie gems. Transfer the dough cutouts to the prepared baking sheets, leaving about 1 inch of space between the cookies. (If making different sizes, group cookies of the same approximate size together for baking.) Place the cookie sheets in the freezer for about 5 minutes before baking to firm up the dough, which will minimize cookie spreading.

Gather and re-roll the scraps; if the dough becomes too soft to work with, shape it into a ball, wrap in plastic, and stick it in the freezer until it’s firm enough to roll again. Continue the process with the remaining dough. (And if you end up eating some delicious dough scraps, I won’t judge. 😉 )

Chocolate Shamrocks 6

Bake the shamrocks for 10-12 minutes, rotating the sheets halfway through. I prefer my cookies on the softer side, so my baking time was on the low end. The tops of the cookies should look a bit dry and may contain tiny cracks. If making round cookies, sprinkle the tops with a pinch of fleur de sel before baking.

Adjust your baking time depending on the size of your cookies; the 10- to 12-minute window is ideal for 2- to 3-inch cookies. Set the baking sheets on wire racks and cool the cookies for about 5 minutes. When slightly firmed up, transfer the cookies directly to the rack to cool completely before filling them.

Chocolate Shamrocks 7

Irish Cream Vanilla Filling
Adapted from Baked Explorations

This filling can be made ahead of time and stored at room temperature in an airtight container for 1-2 days. Cover the surface of the filling directly with plastic wrap to prevent a “skin” from forming. Beat with a spatula to smooth out the filling before using.

  • 5 ounces vegetable shortening, at room temperature
  • 4 tablespoons (½ stick) unsalted butter, cut into pieces, at room temperature
  • 3 ½ cups confectioners’ sugar, sifted
  • ½ teaspoon salt
  • 1 tablespoon pure vanilla extract
  • 1-2 tablespoons Bailey’s (or other brand) Irish Cream liqueur (depending on the desired potency)

Place the shortening and butter in the bowl of a stand mixer fitted with the paddle attachment. Beat on medium speed until the mixture is smooth, creamy, and relatively lump-free. Add the confectioners’ sugar ⅓ at a time, mixing after each addition until just combined. Add the salt, vanilla, and Bailey’s and beat until incorporated. The filling should have a thick, but spreadable, consistency. If it is too thick, add a few drops of water as needed. If it’s too thin or soft, add a few tablespoons of sifted confectioners’ sugar.

Malted Milk Sandwich Cookies 4

Whiskey Caramel Sauce
Adapted from Baked Elements
Makes about 2 cups

This delicious, boozy sauce is originally meant for the Lacy Panty Cakes from the same book, but goes beautifully with these Irish cookies. You can make it ahead and store in the fridge until ready to use for the cookies. Reheat gently in the microwave or over a low burner to a liquid consistency. If you are making it specifically for these cookies, you will have some left over and it’s lovely drizzled over pancakes or French toast.

  • 2 ounces (½ stick) unsalted butter, cut into ½-inch cubes
  • 1 cup firmly packed light brown sugar
  • ¼ cup good-quality whiskey
  • ½ cup heavy cream

Stir together the butter and sugar in a small saucepan over medium heat until smooth; the sugar granules should be completely melted.

Chocolate Shamrocks 8

Add the whiskey and cook for 3 minutes, stirring constantly. The brew will be boiling actively. Add the cream (mixture will sputter upon contact) and continue cooking the sauce for another 3-5 minutes, stirring regularly; it will thicken as it bubbles. Remove the pot from the heat and set aside to cool to room temperature. As the mixture cools, it will continue to thicken to a caramel consistency. Stir occasionally while cooling.

Chocolate Shamrocks 9

You are now ready to assemble the shamrock cookies. Flip half of the cookies over so that the flat side faces up. Transfer the creme filling to a large pastry bag fitted with a medium-sized plain or star decorating tip. Pipe a thick line all the way around the edge of the shamrock (leaving a border of a few millimeters) and fill in the middle. Alternatively, you can use an offset spatula to spread the filling onto the cookie bottoms. Drizzle about 1 teaspoon of caramel over the filling using a tiny spatula or a spoon. Place another cookie, flat side down, on top of the fillings. Press down lightly so that the fillings spread to the edges of the cookie. For round cookies, pipe about 2 tablespoons in a spiral beginning in the center of the cookie, stopping a few millimeters from the edge of the cookie.

Chocolate Shamrocks 12

Repeat this process until all the sandwich cookies are constructed, or make an “assembly line” wherein you apply the creme filling to several cookies, then the caramel, then the tops. Let the cookies set up for about 15 minutes before serving. They can be stored at room temperature in an airtight container for up to 3 days.

Chocolate Shamrocks 13

One more note: After I made these, I thought of another way to make these cookies pop for St. Patrick’s Day. You can make a simple confectioners’ sugar glaze or royal icing, color it green, and drizzle the cookie tops before filling. This fun burst of green would make them even more festive!

Whether you choose to make these as whiskey-laced shamrocks or salt-topped rounds, I would bet money that they will be delicious and enjoyed by all tasters! Remember, they are *extra* yummy alongside their malted cousins. Happy St. Paddy’s Day to ye! 😀

Chocolate Sandwich Cookies 2

© Dafna Adler & Stellina Sweets, 2013.

Share This:

6 Responses

  1. What a fun project! We love these cookies and you’ve made them your own. Wonderful baking…I also read through a few other recent posts and you’ve been busy doing lots of great baking. Lots of good ideas and very professional looking results.

    1. Thanks, Sandra– I appreciate all your kind words! I couldn’t resist making the chocolate dough along with the malted dough from last week, and I thought throwing all that booze in there would be fun for St. Paddy’s! 🙂

Leave a Reply

Share this on Social Media

Most Recent...

Recipe Archive

Get The Latest Recipe

Stellina Sweets in Your Kitchen

Sign up to get notified when new recipes are posted!

You Will Also Love...


Vanilla Bean Cupcakes

Serving Size: 12 Yield: 12 cupcakes or 24 mini cupcakes Ingredients: – For cupcakes: – 1 3/4 cups all-purpose flour – 1 1/2 teaspoons baking

Read More »