Grasshopper Cookie Sandwiches

Dark in color, crispy, and full of deep chocolate and mint flavors, these grasshopper cookies are delicious.

Mint chocolate or grasshopper cookie sandwiches have been on my to-do list for quite some time, and not surprisingly, as the chocolate mint flavor-combo just might be my all-time fave and, umh, who doesn’t love creme-filled sandwich cookies? My introduction to mint-chocolate cookie sandwiches was when I had my first Candy Cane Joe-Joe’s, Trader Joe’s seasonal chocolate cookie sandwiches with peppermint filling. One of my beloved old baked pals introduced me to them, and we would gorge on them at Christmas time, rejecting all manner of homemade treat we were baking, in favor of Trader Joe’s deliciously-minty one.Homemade Oreos - Grasshopper Cookie Sandwiches | Jessie Sheehan Bakes

Cut to several years later (like 10) and I am happy to report that I have conveniently spawned a younger child who shares my deep love of peppermint and chocolate and is quasi-addicted to Newman-O’s Crème Filled Mint Chocolate Cookies. A quick aside: I have some mixed feelings (like a lot of them) about allowing my kids to eat packaged sweets, as 90% of the time there is something sweet and homemade lying around – however, am trying to be a little less rigid (ahem) in my parenting (not to mention the fact that I used to be a peppermint Joe-Joe’s addict), and so, purchased cookies can be found in my cupboards. Grasshopper Cookie Sandwiches | Jessie Sheehan Bakes

And then there’s the broken leg. Baking on one leg is not the easiest of tasks and I have found, over these last three weeks, that baking cookies is something that I can actually do—not effortlessly—but with only a minimal (okay, moderate) amount of cursing. And then—finally—there’s St. Patrick’s day on Thursday, a holiday perfectly suited to eating green-tinted sweets. So, in short, it was the combo of the mint-chocolate loving son, the broken leg, and St. Patrick’s day that left me no choice but to tackle Grasshopper Cookie Sandwiches. Lucky you. 
Grasshopper Cookie Sandwiches | Jessie Sheehan Bakes

I looked here, here, and here for inspiration on these grasshopper cookie sandwiches. I wanted my cookies to be dark in color, crispy, deeply chocolate-y, just slightly sweet, and a tad salty (to combat the sweetness of the minty filling). A bit of black cocoa took care of the color and chocolate flavor, I achieved crispiness (like I did when making wafer cookies for icebox cakes) with a bit of corn syrup, some milk, and no eggs. Finally, a little less sugar and a little more salt took care of the sweet/salty thing I was after. As for the filling, I wanted it to taste like the classic Oreo filling, albeit mint-flavored, and achieved that via vegetable shortening, powdered sugar, water, salt, and extract. I decided to make these grasshopper cookie sandwiches extra creme-filled when I was scooping out the filling and used a slightly too-large scoop – but once I’d done that, there was no going back. Enjoy, peeps, these babies will knock your (preferably green) sox off.

Grasshopper Sandwich Cookies | Jessie Sheehan Bakes
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Grasshopper Cookie Sandwiches

Dark in color, crispy, and full of deep chocolate and mint flavors, these grasshopper cookies are delicious.
Recipe Author Jessie Sheehan

Ingredients

for the cookies

  • 1 1/4 cup all-purpose flour
  • 1/2 cup dutch process cocoa powder
  • 1/4 cup black cocoa powder or sub additional dutch process
  • 1/2 tsp salt
  • 1/2 cup one stick, unsalted butter
  • 1/4 cup vegetable shortening
  • 1 cup granulated sugar
  • 1/4 cup confectioners' sugar
  • 2 tsp pure vanilla extract
  • 2 Tbsp whole milk
  • 1 Tbsp corn syrup

for the filling

  • 3 cups confectioners' sugar sifted, if lumpy
  • 3/4 cup vegetable shortening
  • 1/4 tsp salt
  • water a tablespoon at a time . . .
  • 1 1/4 tsp peppermint extract or to taste
  • a few drops of green food coloring

Instructions

to make the cookies

  • in a medium bowl, whisk together the flour, cocoa powders, and salt.
  • in the bowl of a stand mixer fitted with the paddle attachment, cream the butter, shortening, sugars, and vanilla on medium-low speed until slightly fluffy, about 2 minutes. scrape the sides of the bowl with a rubber spatula.
  • in a separate small bowl, whisk together the milk and corn syrup to combine. add the milk mixture to the butter-sugar mixture with the mixer on medium-low speed; beat until just combined. scrape the sides of the bowl with a rubber spatula.
  • add the flour mixture all at once to the mixer bowl. with the mixer on low speed, beat until the dough just begins to pull away from the bottom of the bowl and forms a cohesive mass. scrape the sides of the bowl with a rubber spatula to fully incorporate all the ingredients.
  • divide the dough in half and place each half on a sheet of plastic wrap. loosely wrap the dough and form each half into a log, about 2 1/4 in wide. roll the logs along the counter, still wrapped in plastic wrap, in order to shape them into perfect cylinders. tighten the plastic wrap around the logs, and refrigerate them for at least 2 hours or overnight.
  • preheat the oven to 350 degrees. once chilled, unwrap one of the logs and use a sharp paring or chef’s knife to cut (using a sawing motion) it into thin slices. about 1/4 in thick; rotate the log as you slice, as the side sitting on the cutting surface will flatten. arrange the slices on an unlined baking sheet.
  • bake the wafers until they appear dry, 10 to 12 minutes, rotating the sheets halfway through the baking time. using a stiff metal or plastic spatula, immediately press down lightly on each cookie to flatten it. let the wafers cool on the baking sheet for 2 to 3 minutes, then transfer them to a wire rack to cool completely. repeat with the remaining wafers.

to make the filling

  • combine the sugar, shortening and salt in the bowl of a stand mixer and beat on medium to medium high speed until combined. add the water, a tablespoon at a time, until the filling is thick but spreadable. add the extract and food coloring and beat until combined.
  • to assemble the cookies: if you want them with extra filling use a 1 1/2 Tbsp cookie scoop to scoop the filling on to the underside of one cookie, place another cookie on top and press down gently. if you'd rather there be less filling use a smaller scoop.

Notes

i froze extra cookies in a zip-top bag and refrigerated my filling and we were eating grasshopper sandwich cookies for a week straight (just saying . . .).

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