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Spooky Halloween Pumpkin Cookies – Double the Fun!

These Halloween Pumpkin Cookies are the perfect treat for your family or neighborhood friends. They have a cute pumpkin face and are filled with rich chocolate frosting.

I love this time of the year. Our neighborhood kids are out playing most of the time, and it is a lot of fun to treat them to fun Halloween recipes

There is something about the cooler temperatures here in NC that brings people outdoors after our hot and humid summer. 

Today, we’ll be celebrating fall by making some spooky pumpkin cookies in the shape of Jack O Lanterns.

Pumpkin cookies on a white plate with words reading "spooky Halloween pumpkin cookies."

Scare up a Sweet Treat with These Home Made Spooky Halloween Pumpkin Cookies.

Imagine the delight at your Halloween party when you surprise your trick or treaters to some  pumpkin Halloween cookies. Just wait for the squeals!

They are the perfect treat to do while trying to solve a Halloween word find puzzle, too.

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Fun Halloween baking is on my agenda for today!  I just ordered a set of festive cookie cutters.  A silicone baking mat also helps when baking any cookies.

If you have not baked with a silicone mat, you don’t know what you are missing.  These ingenious things make perfect cookies every single time with no sticking and no need for oils or parchment paper.

Silicone mats can also be used in other ways around the house. Check out this post for some creative ideas.

It's double the fun with these Spooky Halloween Pumpkin cookies with a chocolate center. Find out how to make them on The Gardening Cook. 🎃🎃 Share on X

Making Halloween pumpkin cookies

So what to make?  Well my options for the Halloween cookie cutters were a bat, two sizes of pumpkins (one really big) a black cat, a haunted house, a witches hat, a ghost and a crescent moon.

I know I’ll probably using all of the cookie cutters during the next two months but for today’s treat, I chose the pumpkin shape.

It’s going to end up as a double sugar Jack-O-Lantern cookie with chocolate center icing that shows through my cut outs.  Fun for the kids and fun to make too!

Start by mixing your dry ingredients and whisking them together.  By the way…don’t you love my duck canisters?  My husband and I love to go antique hunting and I found these for a steal.

He thought I had lost my mind at first but they have grown on him….Cannister with duck, bowl of flour and scoop.

I used a stand mixer to combine my ingredients, because there are five cups of flour and it needs a deep bowl.   Add the flour slowly so it will mix well.mixed cookie dough in a bowl with vanilla and egg.

Then wrap the dough in saran wrap and place in the fridge for an hour or overnight.  It will handle and cut so much better if you make sure to do this, because of all the butter.Finished cookie dough with cookie cutters

Making the pumpkin cookie shapes

Start by rolling out the dough on a floured surface to a 1/4 to 1/2 inch thickness. Then cut your dough into pumpkin shapes using the cookie cutter. But don’t stop there! Let’s give him a face.double Halloween Pumpkin cookies.

Use a sharp knife to lightly score the dough so that it looks like a pumpkin.  Then cut decorative, spooky faces on 1/2 of the cookie shapes. 

The openings will allow the chocolate frosting to show through when assembled and will give the cookie a fun look.

I cut the top layer of cookies a bit thicker than the bottom, since I  massacred the first group I tried to cut spooky pumpkin faces on. Believe me…they cut much more easily if they are thicker.cutting pumpkin faces in dough.

Line your cookie sheet with the silicone baking mat and place your decorative pumpkin cookies on the silicone mat. These cookies are pretty big so I just spaced them out instead of using the circles. Halloween pumpkin cookies on silicone mat

Bake for approximately 6-8 minutes or until the cookies start to turn a light golden brown on the edges (bake longer if you want a crispier cookie).

Let the cookies cool for at least 15 minutes before assembling the cookies.Spooky pumpkin cookies for Halloween cooling

How to Decorate Halloween Pumpkin Cookies

While the cookies are cooling, prepare your icing. The cookies are made somewhat like whoopie pies. The frosting should be thick but spreadable.

Place 1 plain cookie shape and spread a layer of the chocolate frosting on it.  frost the bottom layer of a pumpkin cookie.

Top it with a face cookie and press to combine.   The frosting will sort of ooze up through the face holes and it gives the pumpkin the traditional Jack-O-Lantern look.   Halloween Pumpkin cookie with frosting inside.I love the way these pumpkin face cookies came out.  You can play with the cuttings on the cookies to give each one a slightly different look.

They have a bunch of emotions, from happy to perplexed to grumpy!

How do the pumpkin cookies taste?

In a word, YUM!  The sugar cookie is crisp and tasty and that chocolate icing gives a rich finish to every bite.  They are a double dose of sweet goodness.

I guess I could eat one of these iced pumpkin cookies each day to go with whatever mood hits me, but I think I really oughta save them for the kids. Maybe.  Perhaps.  What do you think?Cute Halloween Pumpkin cookies on a plate.

If you want a bit more color, purchase a tube of Wilton sparkle gel green frosting and decorate the top stem too.Halloween Pumpkin cookies with chocolate centers and green stems.Looking for more fun tips for hosting a Halloween party?  Be sure to check out this article for lots of adult Halloween party ideas, recipes and spooky drink ideas.

Calories in these Halloween pumpkin cookies

Since these spooky cookies are doubled and frosted as well, they are pretty high in calories.  You can lessen the effect by treating them as a dessert rather than a snack! 

Each double cookie has 426 calories.

Pin these cute frosted pumpkin cookies for later.

Would you like a reminder of the recipe for these Halloween pumpkin cookies?  Just pin this image to one of your Pinterest Halloween boards so that you can easily find it later.Cookies on a plate in a collage with words reading "Halloween double pumpkin cookies."

Admin Note: This post for these spooky Halloween cookies first appeared on the blog in September of 2015. I have updated it to add more cooking tips, nutritional information and a video for you to enjoy.

Yield: 18

Spooky Halloween Pumpkin Cookies

Spooky Halloween Pumpkin Cookies

These spooky Halloween pumpkin cookies have a double cookie layer and luscious filling. Make some for your party table today.

Prep Time 5 minutes
Cook Time 6 minutes
Additional Time 10 minutes
Total Time 21 minutes


  • For the cookies:
  • 1 1/2 cups unsalted butter, at room temperature
  • 2 cups granulated sugar
  • 4 eggs
  • 1 teaspoon vanilla extract
  • 5 cups all-purpose flour
  • 2 tsp. baking powder
  • 1 tsp. salt
  • For the frosting:
  • 1/4 cup unsalted butter
  • 3 tbsp cocoa powder
  • 1/4 cup skim milk
  • 2 cups confectioner's sugar
  • 1 tsp pure vanilla extract
  • optional: green Sparkle gel for the stem


1.In a mixing bowl, combine the flour, baking powder and salt. Whisk to combine and set aside.

2.Using the bowl of a stand mixer, cream together the sugar and butter until smooth. Mix in the eggs and pure vanilla extract.

3.Add the flour mixture a bit at a time until well combined. Cover the bowl and refrigerate the dough for at least one hour (or overnight).

4.Preheat oven to 400º F. Roll out the dough on a floured surface to a 1/4 to 1/2 inch thickness.

5.Cut your dough into pumpkin shapes using the cookie cutter. Use a sharp knife to lightly score the dough so that it looks like a pumpkin. Cut decorative, spooky faces from 1/2 of the cookie shapes.

6.Line your cookie sheet with the silicone baking mat and place your cookie shapes on the mat. Bake for approximately 6 minutes or until the cookies start to turn a light golden brown on the edges (bake longer if you want a crispier cookie). 7.Let the cookies cool for at least 15 minutes before assembling the cookies.

While the cookies are cooling, prepare your icing.

8.Melt the butter in the microwave, then stir in the cocoa powder.

9.Add the milk and vanilla extract, and whisk until frothy. Make sure the cocoa powder is very well dissolved.

10.In a stand mixer with a beater attachment, work the powdered sugar into the liquids a little at a time until fully incorporated. The frosting should be thick but spreadable. If it is too runny, add more powdered sugar; if it is too stiff, add in a teaspoon of milk.

11.Use immediately, or store in the fridge, then whip again until fluffy when ready to use. This will keep for several days the fridge, tightly covered.

12Spread the plain bottom pumpkin with chocolate frosting. Place the decorative pumpkin face cookie on top and squeeze so the frosting comes up through the face holes.

13.If you want a bit more color, use Wilton green sparkle gel to decorate the stem area.

Nutrition Information:



Serving Size:

1 cookie

Amount Per Serving: Calories: 426Cholesterol: 89.7mgSodium: 203.3mgCarbohydrates: 60.9gFiber: 1.4gSugar: 35.5gProtein: 5.2g

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Michelle Coles

Thursday 1st of October 2015

I have never used Silicone products before but I do bake alot of cookies and would love to try it out!


Thursday 1st of October 2015

You will never look back once you have tried them!

Candie L

Thursday 1st of October 2015

I would use it for delicious home made peanut butter cookies. Thank you


Thursday 1st of October 2015 favorite!

Rita A

Thursday 1st of October 2015

I mostly have silicone spatulas and not much else.


Thursday 1st of October 2015

Hope you win a mat too!

Leah Shumack

Thursday 1st of October 2015

I love silicone baking pans! We use them for sugar work, cakes and even have some sets that we use for crayons!


Thursday 1st of October 2015

Never thought of using them for crafty stuff and crayons!

John H.

Thursday 1st of October 2015

For making pie crust


Thursday 1st of October 2015

That is one thing that I just started doing and it works great. Doesn't stick at all!

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