Buttery shortbread cookie sandwiches stuffed with creamy chocolate filling make these Pumpkin Shortbread Cookies perfect for Halloween.
My friends. If you have been around here for any length of time, you know that I really love a good cookie. In fact, I think I would be hard pressed to find a cookie that I have passed up.
So it is no surprise that when it comes to the holiday season, making cookies is at the top of my list of favorite things to do. Since Halloween is coming up, I thought that these deliciously buttery shortbread cookies cut into pumpkins would be great – especially when stuffed with chocolate filling.
Be sure to add these Broken Glass Cupcakes to your Halloween celebrations too!
You see. The kids have been too old for traditional Halloween activities for a while now. But that doesn’t mean we don’t celebrate.
I like to whip up something super cute for them to enjoy while they pass out candy. Sometimes it’s a cake or cupcakes. But this time these cookies were just perfect.
Shortbread Halloween Cookies
As if decorated pumpkin shortbread cookies weren’t cute enough. But then I had the idea to make them into little sandwiches.
Let me tell you – that chocolate filling is so tasty when paired with the shortbread. It’s almost like having a little bite of cake.
As you can see – these look more complicated than they really are.
Shortbread only requires a handful of ingredients. But cutting them into adorable pumpkin shapes makes them over the top.
Here are some commonly asked questions
How many can this serve?
This recipe makes about 12 cookie sandwiches. If you decided to keep these as regular cookies, you could get 24 out of this batch. But this will depend on the size of the cookie cutter you use.
Easy to make Halloween Cookies
What is the best way to store leftover pumpkin shortbread cookies?
These cookies will keep well at room temperature if stored in an airtight container for up to 3 days.
HOW DO YOU MAKE Pumpkin Shortbread Cookies?
- In the bowl of a stand mixer fitted with the paddle attachment, whip the butter on high speed for 2-3 minutes, or until it is light and fluffy.
- Add the confectioner’s sugar, vanilla, and salt. Mix again on low speed just until the sugar is fully combined— about 1 minute.
- Next, alternate between adding the flour and milk while the mixer is on low speed. First, add half the flour, then half the milk, then the remaining flour, then the remaining milk.
- Continue mixing on low speed just until the dough forms a ball around the paddle.
- Form the dough into a disk and wrap it in plastic wrap. Refrigerate for 15 minutes.
- In the meantime, preheat your oven to 350F. Line two large baking sheets with parchment paper.
- Lightly sprinkle your work surface with flour and roll the dough out until it is 1/4” thick.
- Use a pumpkin cookie cutter to cut the dough and transfer the cookies to the prepared baking sheet.
- Note: I used a cookie cutter that was 2” in diameter. Additionally, make sure to place the cookies at least 1” apart on the baking sheet.
- Bake the cookies for 10-12 minutes, or until the edges are just starting to turn golden brown. Set them aside to cool completely.
HOW DO YOU MAKE the FILLING for Pumpkin Shortbread Cookies?
- Combine the Nutella, confectioner’s sugar, cream, and salt in the bowl of a stand mixer fitted with the paddle attachment.
- Beat on medium-high speed until it is fluffy and no large lumps of powdered sugar remain— about 2 minutes.
HOW DO YOU Assemble the Pumpkin Shortbread Cookies?
- Once the cookies have cooled completely, spread one cookie with 1-2 tsp of chocolate filling (depending on the size) and top it with a second cookie. Press down gently to make sure the filling spreads all the way to the edge. Note: Be gentle! These are soft cookies.
- To decorate, combine 1/4 tsp of gel food coloring with a few drops of water and stir it until the food coloring is fully dissolved.
- Use a food-safe paintbrush to paint the jack o lantern face, if desired. Allow the paint to dry for at least 20 minutes before touching.
- Note: It is easiest to paint the whole cookie orange before adding the black eyes and mouth.
- Store the cookies in an airtight container for up to 3 days.
Notes
This dough is very soft— feel free to use as much flour as needed to prevent it from sticking to your work surface.
I used this cookie press (link in post) to make the Jack O Lantern face easier to paint.
Should I use salted or unsalted butter?
This is really a personal preference. If you are happy with just a little salt to cut the sweetness, then use salted butter.
I usually use whatever I have on hand & I really don’t pay too close attention to what butter I have. But I typically keep salted butter on hand & I love that little bit of extra salt with the sweet in this recipe.
These days with groceries being more difficult to find – I basically get whatever the store has available at the time and make it work.
To make Pumpkin Shortbread Cookies you will need…
- butter softened
- confectioner’s sugar
- vanilla extract
- salt
- all-purpose flour
- milk
Chocolate Filling
- Nutella
- confectioner’s sugar
- heavy cream
- flake sea salt or kosher salt
To Decorate
- Black, Orange, and Green Food Coloring
- Water
Can these shortbread cookies be frozen?
I recommend freezing either the dough before baking, or the plain cookies after baking. Keep in mind that freezing makes the cookies a bit more crumbly once thawed. Make sure to wrap tightly with plastic wrap and then place in a zip-top bag and label with the date. Use within 4 months.
Can I use a sugar substitute?
I have not personally tried it, so I can’t say how that would turn out. But if you would like to try it, I suggest a product that offers a 1:1 swap. Please let me know how it turns out.
Cookies for Halloween Parties
How do I properly measure the flour?
The official way is to spoon the flour into the measuring cup & level off. This makes sure the flour isn’t packed tightly into your measuring cup, adding more than you need, as that will make your recipe too dry.
However – if you fluff your flour with a spoon, then gently scoop the flour into the measuring cup, taking care to not pack the flour – that should work for this recipe.
Can I use a gluten-free flour?
I’m not sure just yet. I have been meaning to give this a try but haven’t had a chance. If you do try this, I would recommend using a 1:1 flour like this one as I don’t believe it would require additional ingredients that are typically called for when trying to make baked recipes in a gluten-free version. Please come back & tell me how it turned out.
Products I love when making pumpkin shortbread cookies…
This shortbread cookie recipe is SUPER EASY and delicious – and if you’re like me this time of year, then you maybe already have some of these items on hand OR maybe you have never made sandwich cookies before, & you might be a bit nervous – but you’re going to love them. I have made a list below of the things I absolutely can’t live without when it comes to making this cookie recipe.
Halloween Cookies
If you love this Pumpkin Shortbread Cookie recipe, you’re going to love these other treats too. Please click each link below to find the easy, printable recipe!
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Pumpkin Shaped Chocolate Stuffed Shortbread Cookies
Ingredients
Cookies
- 1 cup butter softened (2 sticks)
- ½ cup confectioner's sugar
- 1 tsp vanilla extract
- ½ tsp salt
- 2 cups all-purpose flour
- 3 tbsp milk
Chocolate Filling
- ¼ cup Nutella
- ¼ cup confectioner's sugar
- ¼ cup heavy cream
- ½ tsp flake sea salt or ¼ tsp kosher salt
To Decorate
- Black, Orange, and Green Food Coloring
- Water
Instructions
Make the Cookies
- In the bowl of a stand mixer fitted with the paddle attachment, whip the butter on high speed for 2-3 minutes, or until it is light and fluffy.
- Add the confectioners sugar, vanilla, and salt. Mix again on low speed just until the sugar is fully combined— about 1 minute.
- Next, alternate between adding the flour and milk while the mixer is on low speed. First, add half the flour, then half the milk, then the remaining flour, then the remaining milk.
- Continue mixing on low speed just until the dough forms a ball around the paddle.
- Form the dough into a disk and wrap it in plastic wrap. Refrigerate for 15 minutes.
- In the meantime, preheat your oven to 350F. Line two large baking sheets with parchment paper.
- Lightly sprinkle your work surface with flour and roll the dough out until it is 1/4” thick.
- Use a pumpkin cookie cutter to cut the dough and transfer the cookies to the prepared baking sheet.
- Note: I used a cookie cutter that was 2” in diameter. Additionally, make sure to place the cookies at least 1” apart on the baking sheet.
- Bake the cookies for 10-12 minutes, or until the edges are just starting to turn golden brown. Set them aside to cool completely.
Make the Chocolate Filling
- Combine the Nutella, confectioner's sugar, cream, and salt in the bowl of a stand mixer fitted with the paddle attachment.
- Beat on medium-high speed until it is fluffy and no large lumps of powdered sugar remain— about 2 minutes.
Assemble and Decorate
- Once the cookies have cooled completely, spread one cookie with 1-2 tsp of chocolate filling (depending on the size) and top it with a second cookie. Press down gently to make sure the filling spreads all the way to the edge. Note: Be gentle! These are soft cookies.
- To decorate, combine 1/4 tsp of gel food coloring with a few drops of water and stir it until the food coloring is fully dissolved.
- Use a food-safe paintbrush to paint the jack o lantern face, if desired. Allow the paint to dry for at least 20 minutes before touching.
- Note: It is easiest to paint the whole cookie orange before adding the black eyes and mouth.
- Store the cookies in an airtight container for up to 3 days.
Notes
Nutritional information for the recipe is provided as a courtesy and is approximate. Please double-check with your own dietary calculator for the best accuracy. We at Yummi Haus cannot guarantee the accuracy of the nutritional information given for any recipe on this site.
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