Halloween Cookies: Chocolate Orange Thumbprint Cookies
Happy Monday! Today is the last day of September. That means it’s officially spooky season. And, more importantly, time for Halloween treats. So I thought I’d kick off October (almost) with a tray Chocolate Orange Thumbprint cookies.
Many, many, many years ago, the first time I was in Boston, we went to Swensen’s ice-cream in Faneuil Hall. I can remember standing in historic marketplace in a long line of people reading the never ending list of ice cream flavors. From old favorites like Rocky Road and Peanut Butter Cup to unique combinations like Cantolope and, wait for it . . . Swiss Orange Chip. I was immediately drawn to the chocolate orange combination. And it did not disappoint. I don’t know if it was the searing heat, festival atmosphere of the market, or just the fact that ice cream always tass better on vacation, but the Swiss Orange Chip ice-cream remains my very favorite ice cream experience to this day.
So, I borrowed that flavor combination to make these amazing chocolate orange thumbprint cookies. (You’ll notice that whenever I have the opportunity to combine orange and chocolate together, I seize it! Take these Chocolate Pumpkin Cupcakes with Orange Marshmallow Filling for instance)
Why you’ll love them
I love a thumbprint cookie. And I know you will too. They are quick and easy to make. And even easier to eat. I love how one little cookie can easily meld together to distinct flavors for a unique flavor combination.
And these chocolate orange thumbprint cookies do just that. The chocolate cookie is soft on the inside and full of rich, fudgey flavor. I was eating these straight off the tray before they were filled. The orange filling is marshmallow based, but not too sweet and perfectly balanced by the deep, dark chocolate.
These chocolate orange thumbprint cookies come together in about an hour, including optional chilling time. And they look so pretty and festive. They are the perfect addition to any Halloween parties you’ve got coming up. But also easy enough to bake just because.
How to make chocolate orange thumbprint cookies
Chocolate Cookies
To make chocolate orange thumbprint cookies, begin by preheating your oven to 375℉. Then line 2 large baking sheets with parchment paper, set aside.
In a small bowl, combine 1 ¾ cups flour, ½ cup cocoa powder, ½ teaspoon baking powder and ¼ teaspoon salt. Mix with a whisk and set aside.
Then, in the bowl of a standing mixer, or in a large bowl with a handheld mixer, ¾ cup brown sugar and ½ cup sugar until fluffy (about 2 minutes). Add 2 teaspoons vanilla and beat to combine. Add 2 teaspoons of vanilla and beat to combine.
Once the mixture is fluffy, add dry ingredients to the bowl and beat on low speed. Then increase to medium-high and beat until the mixture forms large crumbs and easily sticks together when pinched. I usually add the dry ingredients in two separate additions to make it easier and to prevent a flour mess.
Scoop out about 1 tablespoon dough and roll into a ball. Press the center of each cookie down gently with a round, 1 teaspoon measuring spoon or the back of a wooden spoon. Then place cookie sheets in refrigerator for 30-60 minutes to chill. This step is optional, but it will prevent the cookies from spreading. too much and help preserve the thumbprint.
Bake the chocolate orange thumbprint cookies in a 375℉ oven for 5 minutes. Check cookies and re-indent the wells in the center of the cookies, as necessary. Be sure to use a spoon–the cookies will be hot.
Continue baking for 4-5 more minutes, until edges are lightly browned and cookies are set. If the wells puffed up again, gently press them back down with the teaspoon when you remove them from the oven.
Let chocolate orange thumbprint cookies cool on the baking sheet for 5 minutes before transferring to a wire rack to cool completely. While they cool, you can make the orange marshmallow filling.
Orange Marshmallow Filling
In the bowl of a stand mixer, , or in a large bowl using a hand mixer, beat together 4 tablespoons softened butter and ½ cup confectioners’ sugar for 2-3 minutes, until light and fluffy.
Then add 7 ounces of marshmallow fluff, ½ teaspoon vanilla and ½ teaspoon orange extract, and a few drops of orange food coloring and beat until well combined. You can add a teensy bit more orange if you want a stronger flavor, but beware, extracts pack a lot of punch.
There are lots of ways to fill these cookies. In my experience the easiest is to use a piping bag. If you have one, fit the bag with #12 round tip. Spoon the marshmallow filling into the bag, and a dollop to each cookies. If you don’t have a piping bag, a zip top bag with the corner cut off also will work to pipe and fill the cookies. Or you can use a small spoon.
Store cookies in an airtight container for up to 5 days. Or freeze for up to 3 months.
Enjoy
These chocolate orange thumbprint cookies are the perfect afternoon snack. They pack beautifully in a lunch box. And they would be an excellent after trick-or-treating treat.
You could even add some Halloween sugar or sprinkles. Or add candy eyeballs to up the wow factor!
These chocolate orange thumbprint cookies are also fabulous drizzled with a chocolate ganache. Check out the recipe notes for more information.
They pair perfectly with a glass of cold milk or a cup of tea.
And you can bake them ahead and freeze them too. I’ve frozen them both filled and unfilled and either way works great. If you do fill them first, just be sure to let the filling set and insert parchment paper between layers so they don’t stick to one another.
Off we go!
P.S. If you like thumbprint cookies as much as I do, you need to try these Nut Free Chocolate Thumbprint cookies too.
Chocolate Orange Thumbprint Cookies
Equipment
- 2 baking sheets
- Parchment paper
- oven
- small mixing bowl
- Large mixing bowl
- Stand mixer or hand mixer
- piping bag or ziplock bag
Ingredients
Chocolate Cookies
- 1 ½ cups all-purpose flour
- ½ cup cocoa powder
- ½ tsp baking powder
- ¼ tsp salt
- 1 cup (2 sticks butter), softened
- ¾ cup brown sugar
- ½ cup sugar
- 2 tsp vanilla extract
- ½ cup granulated sugar for coating
Orange Marshmallow Filling
- 1 7-ounce jar marshmallow fluff
- ½ cup powdered sugar
- 4 tbsp butter 1/2 stick
- ½ tsp vanilla extract
- 1 tsp orange extract
- 2-3 drops orange food coloring
Instructions
Chocolate Cookies
- Preheat oven to 375℉. Line 2 large baking sheets with parchment paper, set aside.
- In a small bowl, combine 1 ½ cups flour, ½ cup cocoa powder, ½ teaspoon baking powder, and ¼ teaspoon salt. Set aside.
- In the bowl of a standing mixer, or in a large bowl with a handheld mixer, beat 1 cup softened butter, ¾ cup brown sugar and ½ cup sugar until fluffy (about 2 minutes). Add 2 teaspoons vanilla and beat to combine.
- Add dry ingredients to the bowl and beat on low speed, then increase to medium-high and beat until the mixture forms large crumbs and easily sticks together when pinched.
- Measure out 1 tablespoon portions of dough and roll each into a ball.
- Press the center of each cookie down gently with a round, 1 teaspoon measuring spoon or the back of a wooden spoon.
- Place cookie sheets in refrigerator for 30-60 minutes to chill. This will prevent the cookies from spreading.
- Bake in 375℉ oven for 5 minutes. Check cookies and reindent the wells in the center of the cookies. Be sure to use a spoon – cookies are hot.
- Continue cooking for 4-5 more minutes until edges are lightly browned and cookies are set. If the wells puffed up again, gently press them back down with the teaspoon when you remove them from the oven.
- Let cool on the baking sheet for 5 minutes before transferring to a wire rack to cool completely.
Orange Marshmallow Filling
- In the bowl of a stand mixer, beat together 4 tablespoons softened butter and ½ cup confectioners' sugar for 2-3 minutes, until light and fluffy.
- Add 7 ounces marshmallow fluff, ½ teaspoon vanilla and ½ teaspoon orange extract until well combined.
- Fit a piping bag with #12 round tip. Spoon the marshmallow filling into the bag. A zip top bag with the corner cut off also will work to pipe and fill the cookies. Or you can use a small spoon.
- Pipe and fill the cookies with the marshmallow cream.
- Store cookies in an airtight container for up to 5 days.
Notes
Feel free to experiment with other flavor fillings. Raspberry, strawberry, and mint would all be delicious! Just swap out the orange extract and food coloring color.
These cookies are also excellent filled with chocolate ganache. For an easy ganache, place 1 cup chopped dark chocolate in a heat proof bowl (or use good chocolate chips), then heat 1 cup heavy cream in a small saucepan just to simmering. Pour the heavy cream over the chocolate and allow to rest for 4-5 minutes until chocolate melts. Stir in 1 teaspoon vanilla and whisk until smooth and shiny. Use a small spoon to fill the cookies.
