I’m not gonna lie: These Chocolate Whole Wheat Sandwich Cookies with Raspberry Filling are a production. It took me the better part of an afternoon to make them—the dough chills for a few hours before rolling, cutting, and baking, and then there’s the post-bake cool, the post-decorating rest, and the final sandwich-making. But oh my, are they worth it. Just look at those adorable, generously sized honeys. Wouldn’t your honey love to eat one?
One good thing about the many steps involved, if you’re the parent of a youngun: These are perfect for Nap-Time Cooking. Make the dough during the morning nap, and roll and bake during the afternoon nap. Decorate and fill whenever you can—after baby’s bedtime, or when it’s your partner’s turn to hang out with the wee bairn.
The cookies themselves are a chocolaty, not-too-sweet nibble. I’ll make them again, without the production that follows.
If you’ve got older kids, there’s plenty of opportunity for “help,” too. I made the cookies themselves while Harry was at school, but he and his buddy P helped me dunk and decorate—turns out they both preferred the white chocolate, which personally I can’t stand so I’m not even sure why I had any in my kitchen. Last night while Harry slept I made the filling and sandwiches, a little surprise for my junior Valentine.
Here’s what they look like when a pair of four-year-olds is through decorating.
Chocolate Whole Wheat Sandwich Cookies with Raspberry Filling
Inspired by Joy the Baker
Makes 13 sandwiches
Weight Watchers: These are complicated—PointsPlus will depend on the size of your cookie cutter and how much more you do to them. I got 26 three-inch hearts, which came out to 2 PointsPlus each. Dipping in chocolate and decorating added another 2, and the filling is another 2-3. I’m counting a decorated sandwich as 9 and an undecorated sandwich as 7. Definitely a treat, though the plain cookie is quite WW-friendly.
1 cup whole wheat flour
1/4 cup plus 2 tablespoons all-purpose flour
1/4 cup plus 2 tablespoons cocoa powder, plus more for rolling
1/2 teaspoon baking powder
1/2 teaspoon espresso powder
a generous 1/4 teaspoon salt
1/2 cup (1 stick) unsalted butter, at room temperature
1/2 cup dark brown sugar
1/4 cup granulated sugar
1 large egg
1 teaspoon vanilla extract
Good-quality semi-sweet, milk, or white chocolate for melting
Whatever decorations, sprinkles, etc. you like
Raspberry filling (recipe follows)
- In a medium bowl, whisk together the flours, cocoa powder, baking powder, espresso powder, and salt. Set aside.
- Using an electric mixer (stand or hand-held) and a large bowl, beat together the butter and sugars until smooth and dark tan. Scrape down the bowl and add the egg and vanilla. Beat on medium speed until the mixture is fluffy, about 2 to 3 minutes.
- Add the dry ingredients all at once (if you’re using a stand mixer, you may want to throw a kitchen towel over it to prevent a cloud of cocoa-colored dust from floating through your kitchen). Mix on low speed until it’s barely incorporated. Stop the mixer and finish mixing by hand—I find a silicone spoonula helpful here. Lay some plastic wrap on the counter and empty the dough onto it, then cover with another layer of plastic wrap. Press gently to form a large disk, then wrap tightly and chill for at least 2 hours. (The dough will hold in the fridge for at least a day, possibly more.)
- Place a rack in the upper and lower thirds of the oven and preheat to 350° F. Line two baking sheets and set aside.
- Prepare your work area (and be prepared for things to get a bit messy): Grab your cookie cutter, rolling pin, and offset spatula. Put several tablespoons of cocoa powder into a small bowl, and sprinkle some lightly onto a layer of wax paper or a rolling mat—I use a RoulPat Pastry Mat.
- Divide the chilled dough in half and place one half on your cocoa-ed surface. Return the other half to the fridge. Lightly cocoa the rolling pin and roll out the dough to a 1/4-inch thickness. Cut out cookies (put the cuts as close together as possible) and transfer to the prepared baking sheet with the offset spatula. Bake for 10 to 12 minutes, rotating sheets halfway through. Remove from the oven and leave the cookies on the baking sheets for a few minutes, until they’re firm enough to transfer to a wire rack to cool completely. Repeat with the remaining dough, re-rolling no more than twice, until it’s all cut and baked.
- Once cookies are completely cool (in my chilly kitchen it took 30-40 minutes—a good time to make the filling, recipe below), melt your choice of chocolate in a microwave or double-boiler. Put a layer of wax paper (or clean and re-use your RoulPat) under the cooling rack, and put the decorations nearby. Dunk half the cookies, one by one, into the melted chocolate, replace them on the rack, and sprinkle quickly with decorations. (Decorating is a good job for the kids.) Allow the chocolate to set completely before proceeding.
- Spread the undersides of the un-dunked cookies generously with raspberry filling, and top each with a decorated cookie. Press lightly. Done! Now pat yourself on the back for taking on such a complicated task.
Makes enough for 13 three-inch sandwich cookies
3 tablespoons raspberry jam
3 tablespoons butter, at room temperature
3 tablespoons vegetable shortening (I use trans-fat free)
1/2 tablespoon milk
pinch of salt
1 1/2 to 2 cups confectioners sugar
- Warm the jam slightly in the microwave, then pass through a strainer to remove the seeds. Stir for a minute or two to cool it down, then add the butter, vegetable shortening, milk, and salt. Whisk vigorously until everything is completely blended—you can use a hand mixer here, but I often find that more difficult with relatively small quantities.
- Sift 1 1/2 cups of confectioners sugar into the bowl and whisk until well combined. This may take several minutes, so expect a tired arm afterwards. If it seems too soft, add more sugar—you want a relatively stiff filling, or else it’ll squish out when you bit into the cookie.
MAKE BABY FOOD: These are safe for babies, but because of all the sugar I’d reserve them for very special occasions.
* Lloyd Dobler: Call me. Stephen never has to know.