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 cookie recipes. There is something about the cooler temperatures here in NC that brings people outdoors after our hot and humid summer. 
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!
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Fun Halloween baking is on my agenda for today! I just ordered a set of festive cookie cutters. I want to be able to bake my way through the next few months and the cookie cutters are the perfect size and have so many holidays themes in them.
I also just got a fantastic new silicone baking mat from Chef Clever that is just itching to get a work out.
I’ve used lots of baking mats in my time and I love this one. It is the perfect size, is thicker than the ones I have tried, and has circles for placing cookies as well as rulers on the edges for measuring too.
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.
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….
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.
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.
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.
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.
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. 
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.
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. 
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. 
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?
If you want a bit more color, purchase a tube of Wilton sparkle gel green frosting and decorate the top stem too.
Looking for more fun tips for hosting a Halloween party? Be sure to check out this article for lots of Halloween tips, 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.
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.
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.
Spooky Halloween Pumpkin Cookies
These spooky Halloween pumpkin cookies have a double cookie layer and luscious filling. Make some for your party table today.
Ingredients
- 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
Instructions
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:
Yield:
18Serving Size:
1 cookieAmount Per Serving: Calories: 426 Cholesterol: 89.7mg Sodium: 203.3mg Carbohydrates: 60.9g Fiber: 1.4g Sugar: 35.5g Protein: 5.2g
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Those cookies look so yummy! They are definitely the cutest “spooky” cookies I’ve ever seen! I think it’s neat that you’re using a silicone baking mat. I’d love to use one to bake cookies. I’ve tried greasing pans and using wax paper, but they always end up messy. I think using silicone baking mats are really the way to go! Thanks for the recipe, I can’t wait to try it!
Jess
Thanks Jess. Be sure to apply for the giveaway. There will be five winners this time! Carol
Dear Lord, I would use this for everything from baking cookies to roasting chicken breasts.
I love them too Meghan. so versatile! Carol
I’ve never used silicone baking mats but I’ve heard very good things about them. It always seems that my cookies come out uneven some are burnt on the bottom some not cooked enough so hopefully this will help solve that problem.
You never use anything else once you have tried them. I love them and use them all the time. Carol
I love to back cookies. However, I have never used silicone baking sheets. It would be wonderful to win this giveaway.
Best of luck with your entry Alice! Carol
I find that silicon spatulas and cupcake liners are indispensible tools while baking.
Me too Neha. Just love them! Carol
I love these mats. I use them for cooking french fries, cookies, and lots of other things.
Hi Caroline. Many people just think cookies, but they really are so versatile! Carol
I would use them to replace wasteful and expensive parchment paper when I bake sticky cookies like macaroons.
Me too Cynthia. It is nice to save money and have the product work really well too~ Carol
I use them for baking
I love my spatulas! I use them for baking and for cooking things on the stove! I love how versatile silicone can be!
Me too Lindsey. They are just wonderful! Carol
I’ve never used silicone products before but I would love to try some out. I like the idea of cookies not sticking and not having to use paper or spray.
Hi Connie. I started using them about 6 months ago and I am hooked now. Just love them. Carol
I would use it for baking cookies with my kiddies!! Thanks!
Hi Amy. This mat is great for that since it has the circle spacing. The kids will love it. Carol
I have silicone mats for just 2 of my baking sheets — I have used them for everything from baking meatballs or chicken to cookies, and other treats, as well as seasoned baked potato wedges! They are amazing. I haven’t tried the other types of products out there — so can’t comment on those… but LOVE the sheets! Clean up is easy, sheets stay super clean, etc. Highly recommend them!
I am the same Johannah. I use them all the time! Carol
I have never used a silicone baking mat before but I have heard great things about them. I really enjoy baking so I think this would make the process smoother and not create such a mess!
It really does Jenna! Carol
I have two silicone spatulas and they’re great!
Hi Emily. I don’t have the spatulas yet, but hope to get some soon. Carol
I use them whenever I bake cookies!
Hi Becca. They are perfect for that aren’t they? Carol
to bake cookies and herbal candies.
Hi Tina. Herbal candies! Would love the recipe. Carol
i dont have nearly enough silicone items in my kitchen but i do have silicone spatula and also cupcake liners
Best of luck on the silicone mat Lisa. Hope you win! Carol
I’ve never used a silicone baking mat but just two days ago I made cookies out of rice flour (reg and glutinous) and tapioca starch – they’re delicious except for the bottoms – they tend to come out a little too crispy and brown – maybe a silicone mat would resolve that.
If it does they would be almost as good as wheat cookies 😀
thanks!
Love your pumpkin cookie idea!
Thanks Debbie. Those cookies just slid right off the mat and were perfectly cooked on the bottom. Carol
I have some silicone cupcake liners and I really like those! Thats the only silicone I’ve tried
I use those too Ashley and love them. Hope you win the baking mat so that you can give that a try too! Carol
I have never used silicone baking mats, but I have heard great things about them. I LOVE to bake, and my family loves to sample. 🙂
I never have used silicone products before but I really would like to.
You are in for a treat if you win, Marlene. These mats are wonderful. Carol
I use it to knead bread dough.
Now that’s a great idea Patrick. Had not thought of that. Carol
I have never used silicone mats before but have heard good things about them. I would love to try them.
Best of luck Melissa. Carol
I need this for the upcoming Halloween baking season!
Hi Denise. It is such a fun time of the year isn’t it? Carol
I would use it to make cookies
Hope you win Eldon! Carol
I have never used silicone baking mats but I would love to use them for Halloween and Christmas cookies. I’ve used silicone baking cups for cupcakes because I love being able to re-use them.
That is the best part of Silicone products Jillian. Carol
I have never used silicone baking products before but look forward to using them!
Good luck Kim. Hope you win. Carol
Never tried using silicon product yet.would love to, thanks
You will love them once you try them Jessica. Best of luck. Carol
I love silicon for easy clean up. I have bundt pans and muffin pans made from silicon, I have homeade popscicle molds in silicon and candy tray. I have a silicon mat in my microwave and my oven, I even have one for my bbq. They are amazing.
I didn’t know they made bundt pans Patricia. Must check them out. Carol
I don’t have any silicone baking stuff yet.
Good luck on the giveaway Tabitha! Carol
I have silicone muffin pans and I like how nothing sticks and easy to clean. Would like to see how the baking mats work.
It’s amazing isn’t it Audra? Carol
Perfect for making cookies with my daughters!
So nice that you bake with your daughters Stephen! Carol
Baking cookies and using it for bread dough basically anything they are very versatile and I simple to use. I’m a fan!
Me too Ali. Love it all. Carol
I have never used silicone in my kitchen before. I would love to try it for baking cookies and muffins!
You will never turn back if you do. It’s great stuff. Carol
I have some silicone (I think they’re silicone?!) cutting boards that I love.
I wonder if they are silicione Stephanie. My understanding is that you are not supposed to cut it? Carol
I have several – basting brushes, molds, measuring cups and spatulas to name a few. I love the silicone baking products that I have.
I don’t have measuring cups, but do have the other items. Carol
I have a silicone spatula
I think I started with those and just added more as I could.
I had silicone muffin pans and liked those.
Me too Jessica. Carol
I use silicone muffin pans as well as bread pans, I was amazed at how well they worked compared to traditional metal pans 🙂
Their ability to stand the heat is amazing. Carol
The only silicone product I have used to bake are muffin pans! I would love to try other products!
I have used the muffin cupcake liners but not muffin tins yet. Carol
I would use it for baking.
Thanks Ana. Carol
I have two at home and use one for cookies and baking treats and the other I use for chicken fingers and fish sticks, etc.
That is a good idea Wendy. Carol
I have never used silicon baking items but, I have been very curious about them.
Hi Jennifer. You will love them once you have tried them. Carol
I have not tried these yet.. I would use them for baking cookies and other treats to using them for cooking parts of meals. This would be very nice to have. I always so a lot of baking and bring so many meals out to my husband and our workers from now until the end of the year. They can put in 12 – 20 hours a day depending on the weather and are always happy to see home made food and treats.
Best of luck with your entry Ronda. Carol
I’ve never used a silicone baking mat, but that reminds me I need to make some cookies.
Hi Ruy…LOL. Good luck on your entry. Carol
Your cookies are adorable! I have a lot of silicone baking pans but for some reason have not taken the plunge to get a silicone baking mat. I would use the heck out of one! I love my silicone pans and the mat would be a nice change from going through yards and yards of parchment paper on my cookie sheets!
Hi Angelica. I have lots of silicone products too, but the baking mat is the one I use all the time. Carol
I would like to use it while baking holiday cookies!
Hi Liberty. It is such a fun time of the year isn’t it? Carol
I would love to use a silicon baking mat for baking cookies :). I’ve never tried it but I hear they work amazingly!
They really do Natasha. I just love mine. Carol
I would make cookies for our Halloween party!
It is such a fun time of the year isn’t it? Carol
I have never used a silicone baking product, but I’m eager to try one! I think I’d use it to bake cookies.
Hi Alisha. Silicone mats are so versatile. I use them for all sorts of baking methods. Carol
I use silicone baking mats most for cookies!
Hi Kelly. I use them for baking too, but also a lot for things like roasted veggies. Carol
I love my silicone baking mat. I haven’t had a cookie stick since I bought it.
That is great to know Ashley. Thanks for sharing. Carol
I use silicone muffin tin liners and like them very much.
Hi John. I have some of them too and really like them. Carol
I have silicon spatulas and spoons and love them they are so slick to use and easy to clean
Same here Wendy. They are just great. Carol
This summer I got silicone muffin cups and fell in love with the material. I now have the silicone scrapers, too.
Hi Kimberly. That sounds just like what happened to me. Hope you win a silicone mat to add to the collection. Carol
I have never used a silicone product in the kitchen before but this looks like it would be awesome for cookies and cinnamon buns!
Hi Andrea. I’ve never done cinnamon buns on them but I bet they would work great. Carol
never used a silicon baking mat before. But Id love to ! btw, in rafflecoptor form, I accidentally hit enter before finishing my twitter handle entry , it is @SummersSusan , not @SummersSusa
Hi Jaimee. Thanks for the update on the twitter handle! Carol
I have a silicon mixing spatula, I love it.
I have some of those too Jaimee and also love mine. Carol
I have never used them, but would love to for the upcoming holiday baking!
Hi Leslie. You will never look back once you try them. Carol
we havent used it yet – been wanting too – just not the finances to buy new baking products
Hi Brenda. Best of luck with the contest. Carol
Most of my tools are silicon.
Hi Joni. I am gradually changing over as I can afford them. Carol
my scones and cookies always stick hopefully a mat will help thank you for having this giveaway
Best of luck Sue. I have never had anything stick to my baking mat. It’s so neat. Carol
I would love to try some silicon muffin liners, there would be so many good uses actually.
Hi Crystal. I used the muffin liners earlier this year and like them, but the product I use all the time is my baking sheet. Carol
Definitely for buns and cookies
Thanks Stephanie. Best of luck with your entry. Carol
So far I’ve used them for baking cookies
HI Brenda. They are great for roasting veggies and baked oven fries too. Carol
I use them to bake cookies.
All I have is a silicone spatula, but that works great!
Hi Michelle. Hope you win the mat too! Carol
I’ve only recently picked up a mat, but I like rolling out dough on it and even cutting out cookies and then of course baking said cookies!!
Hi Amber. I just started using mine for rolling out dough and love the way it does it. Carol
I would use it to roll out pizza dough, and to roll out dough for cookies and biscuits I have always wanted one for the Fall baking. Ellen
They have so many uses don’t they Ellen? Best of luck with your entry. Carol
Definitely for all my baking.
I feel they are a life saver. I use them everytime i bake either desserts or meals, they make cleanup alot simpler
That is one of the thinks that I like best about them too – their clean up! Carol
I actually don’t use silicon products in the kitchen yet but I have been wanting to give them a try. I’ve heard really good things and I bake all of the time. Thank you so much for the chance to win!
You will love them once you start using them! Best of luck with the giveaway. Carol
I use silicone potholders, silicone muffin cups and silicone travel coffee mug holders. I love how it protects your hands from the heat of things! I’ve never tried the baking sheets. I would love to win one! Thanks for having the giveaway!
Hi Diana. I must look for the silicone pot holders. I had not hear of those! Carol
Just Google them. Many retailers carry them. I have a square one that is the trivet style & a pair that just cover the thumb & fingertips kind of like a puppet without covering your whole hands. I tried an oven mitt style but my hands are so tiny that I was way too clumsy with it on. Don’t forget to use the retail store coupons if available like many kitchen supply retailers have online. Happy shopping! 🙂
I’ve never used one before but would love to try a mat for cookies.
HI Jennifer. Good luck with your entry! Carol
I have a couple of silicone specialty pans that I use, but not very often, and a set of silicone basting brushes. The only thing wrong with them is the difficulty in getting them clean after use!
I haven’t noticed that. I soak them in water right after using them and then wash them later. They seem to come up very well. I have used other silicone mats that were hard to clean but this one is a breeze. Carol
I think I would use it the most baking cookies.
Hi Nicole. I did use mine the most for that in the beginning but now use in them in all sorts of ways. Carol
I have use silicon baking mat before helps so much for bake goodies not to stick.
Aren’t they great Jill?
Hope you win another one Jill!
I’ve never tried using any silicone bakeware, but would love to try!.
There are so many things I could use this mat for. We bake cookies a lot. Toasting garlic bread. Making little cheese crunchies. So Many things!
Me too Crystal. I love to make roasted veggies on them. Yum! Carol
I currently use silicone cupcake liners!!
I have two sets of those too, Ashley and love them!
I use these to roll out fondant.
I bet they work really well for that Laura.
i love to bake cookies and i like the way silicone mats cook them evenly.
That is my favorite part too Jenn. They never stick and cook so nicely.
I do not have any silicone baking products, however, I do have silicone spatulas and love them.
The Pumpkin Cooks look delicious.
Thanks Tammy! They were really tasty!
They are great for using in non stick pans.
I have never owned any silicone baking products but would use them daily in the kitchen. I would love the silicone baking mat,, silicone spatulas as well as a silicone muffin pan and bread pan. There seems to be so many silicone products that I would get a lot of use from.
I am slowly getting a collection and love them!
I havent tried any silicone baking products, but I would sure want to ! Thanks so much for the chances to win.
Best of luck with your entry!
I would like to use it to make cookies.
They are great for this. Best of luck with your entry.
I would use it for baking.
For making pie crust
That is one thing that I just started doing and it works great. Doesn’t stick at all!
I love silicone baking pans! We use them for sugar work, cakes and even have some sets that we use for crayons!
Never thought of using them for crafty stuff and crayons!
I mostly have silicone spatulas and not much else.
Hope you win a mat too!
I would use it for delicious home made peanut butter cookies. Thank you
Yum…my favorite!
I have never used Silicone products before but I do bake alot of cookies and would love to try it out!
You will never look back once you have tried them!