I love baking Halloween-themed desserts and these homemade chocolate sandwich cookies are reminiscent of Oreos, improving on a classic, if that’s even possible. A dark and dreamy chocolate cookie sandwiching a creamy vanilla filling – it’s a winner. You can tint the filling according to the holiday – red for Valentine’s Day, green for Christmas. You can even swap out the vanilla for peppermint extract for a Christmas Oreo. I’ll have to remember that come December.
Please note these cookies are bigger than traditional Oreos – closer to the jumbo soft Oreos than the traditional crisp cookies -but you can adjust to any size you like. Ok, let’s get started.
Whisk together your cocoa, flour, baking soda and salt like so.
After your dough comes together, you chill it in the bowl in the fridge for a bit. Next you roll it into a cookie dough log – it looks like a giant tootsie roll – and into the freezer for a short bit.
After it’s chilled again, you slice the dough into even slices of deliciousness. I dare you not to eat a raw slice. And yes, that’s a ruler in the photo below. I use a ruler when I’m baking sometimes to make sure my measurements are on point. I am spacially challenged.
Onto the parchment-lined cookie sheets and while the cookies bake, get the filling together. Take note – the cookies aren’t perfect circles. It’s ok, they’re homemade and they should look like it.
Here’s your thick and creamy buttercream filling.
Spread the filling on half of the cooled cookies – don’t be stingy. More is better.
Sandwich with a second cookie and the Halloween Oreo is born. Heads up – these are actually better the next day (and the next!) as the cookies soften up and start to absorb some of the filling.
Super-sized Homemade Halloween Oreos
Makes 16-20, depending on size of cookies
For the cookies:
1 cup melted butter
3/4 cup sugar
1 teaspoon vanilla
1 cup melted chocolate chips
1 1/2 cups flour
3/4 cup unsweetened cocoa powder
1 teaspoon kosher salt
1/2 teaspoon baking soda
For the filling:
1/2 cup butter, room temperature
1 2/3 cups confectioners sugar
1 teaspoon vanilla
1 tablespoon milk
pinch of kosher salt
Natural orange food coloring (Check your health food aisle, local health food store or head online to find it. I like India Tree brand, which is available on Amazon. If you want to skip this step, you can make the cookies with non-tinted filling – still delicious!)
In a medium bowl, whisk together the butter and sugar until well combined, about 2 minutes. Whisk in the vanilla and melted chocolate. Whisk in the egg and combine well. In a separate bowl, whisk together the flour, cocoa, salt and baking soda until combined. Add flour mixture to the chocolate mixture and stir until well combined. It will be the consistency of thick brownie batter. Cover and chill in the refrigerator 1/2-1 hour.
Transfer chilled dough to a sheet of wax paper and shape into a log about 2 inches in diameter and 11-12 inches long – or smaller in diameter if you want the cookies to be closer in size to traditional Oreos. Place log along the edge of wax paper and roll it into a smooth cylinder. Twist ends to secure and keep shape. Freeze 1/2 hour, checking twice to reshape if necessary.
Preheat oven to 325 degrees F and line two cookie sheets with parchment paper. Unwrap dough and cut into quarter inch slices (you’ll have 32-40) and place on baking sheets. Bake for 16-20 minutes or until cookies are firm to the touch. Let cool and prepare the filling.
With a mixer, beat the butter for a few minutes until smooth. Add sugar and vanilla and beat until smooth. Add milk and salt and beat until smooth. Add natural food coloring until you achieve desired tint. Place a tablespoon or so of filling on the bottom of each cookie and sandwich with a second cookie. Store tightly wrapped at room temperature for up to 3 days.
Looking for more Halloween treats? Try these:
Plan B Mom is a mostly-stay-at-home mom of 3 who works from home but sees her main job as managing her family. When she is not taking care of her 13-year old and 11-year old girls, 9- year old son, yellow lab, and husband – she is baking, running, carpooling, or helping with homework. She tries to stay organized to keep life running smoothly – or at least catastrophes at bay. Follow her on Twitter at @PlanBMom.