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Jack Skellington Pie for Halloween | Cherry Balsamic Pie

This Jack Skellington Pie is a fun and spooky way to serve up a halloween pie. The sweet and syrupy cherry balsamic pie will tantalize your taste buds!

Jack Skellington Balsamic Cherry Pie for Halloween by FamilySpice.com

My kids may be teenagers, but that doesn’t mean we don’t celebrate Halloween. On the contrary. I think they miss those days even more than I do. This year, their baby cousin requested that his big cousins join him trick-or-treating. It’s the cutest thing watching this 3-year old boy (and his 1-year old brother) play with his teenage cousins like they are all toddlers.

And a Halloween can’t come by without me attempting another fun and cute Halloween dessert, despite having teenagers living at home. No cutesy cupcakes or silly cookies. Instead, I think this fun Jack Skellington Pie is perfect for kids of all ages.

Rolling Out Pie Dough by FamilySpice.com

Best Filling for Cherry Pie

One of my favorite desserts is pie probably because I absolutely adore fruit based desserts. So that means I can’t say no to apple pie, peach pie, strawberry pie or even a cherry pie. But please don’t serve me a pie with that sugary canned fruit filling. For the best pie filling, I always use fresh fruit or frozen for my pie filling.

And this Balsamic Cherry Pie is no different. Although it is October and fresh cherries are hard to come by, I used frozen red cherries. Did you know that frozen fruits and vegetables hold their nutritional value as well as fresh? They are usually flash frozen at the peak of freshness, making them perfect for pies when their fresh counterparts are out of season.

Stenciling Jack Skellington Balsamic Cherry Pie for Halloween by FamilySpice.com

And the other perk of using frozen cherries? I don’t have to pit all 2-pounds of them! Yes, it’s a lazy perk, but a perk no less. I added balsamic vinegar to the mix as it added a wonderful sweet and sour element to the filling. I have also made this pie with a little rosemary, too, and it is quite heavenly.

But do note, for some pies, fresh fruit is the preferred choice. For example, strawberry and raspberry pie is best using fresh fruit because it stays firm. Their thawed counterparts turn to mush, and so will your pie.

How to Make Jack Skellington Pie Crust

The pie crust I used for this pie was my olive oil crust recipe from my cookbook. But I have also made a homemade butter pie crust and refrigerated pie crust. They all work great with the Jack Skellington template. So feel free to choose your favorite pie crust recipe for this balsamic cherry pie.

You will need two pie crusts to make this Jack Skellington pie: one for the bottom and the other for the Jack Skellington top.

Stenciling Jack Skeleton Balsamic Cherry Pie for Halloween by FamilySpice.com

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I found the Jack Skellington image online and resized it so it would fit perfectly in my 9-inch pie crust. You can find the template here. Remember that you will have a mirror image as you trace and outline the template onto your pie crust. For this face, I wasn’t too concerned about this.

I place the paper over my crust and traced the image with the tip of my knife. After I removed the paper, I used my sharp knife to cut the slits and eyes out. Basically, everything that is black will be cut and the balsamic cherry filling will be bubbling through. I like to use a silicone rolling mat when working with pie crusts as it makes it super to easy to transfer to the pie pan.

Stenciling Jack Skeleton Balsamic Cherry Pie for Halloween by FamilySpice.com

How to Assemble Your Jack Skellington Pie

Traditionally, many bakers like to fold the pie crust into fourths and then unfold it into the pie plate. But because there are so many openings and slits with the top of the crust, I just use the silicone mat and then flip the final pie crust over the pie filling.

I won’t lie. Pie making is challenging. It’s right up there in difficulty with decorating cookies. But practice does help and I find it so relaxing and rewarding. More so than piping fancy icing decorations onto a sugar cookie! But no one in my family seemed to notice or care about the imperfections of my pie edges!

Assembling Jack Skeleton Balsamic Cherry Pie for Halloween by FamilySpice.com

Once the top pie crust is in position, just peel off the silicone mat and remove the excess pie crust. I pinched the two pie crusts together and then folded the edges underneath the pie to create a thick rim. For the scalloped edges, I held the edge with my thumb and index finger of my left hand and pressed the dough between them with the index finger of my right hand. There’s a great video tutorial showing you how to do it here.

Once the two crusts were sealed and ready, I used the knife tip to spread out the mouth slits and eyebrows more. I brushed the raw pie with an egg wash and a sprinkling on sugar. I used regular granulated sugar, but the bigger sanding sugar crystals are ideal. Next time I’ll get it right!

Assembling Jack Skeleton Balsamic Cherry Pie for Halloween by FamilySpice.com

I baked the pie at 425ºF. My oven burnt the edges of my pie, which upset me. No perfect golden photogenic crust for me. My Professor was sweet and said that no one would care about the burnt edges. My husband liked the spooky effect. I adjusted the baking temperature in the recipe so it wouldn’t burn so quickly for you.

And no one really minded the burnt edges of the pie, except me. I loved the balsamic cherry filling. Even though this was the pie I ate to celebrate my birthday, I didn’t mind the spooky Jack Skellington pie crust. That’s what we get when we have October birthdays in my house, a halloween pie! Just ask my daughter, who is also an October baby, about her halloween ice cream cake last year!

Ready to Bake Jack Skeleton Balsamic Cherry Pie for Halloween by FamilySpice.com

And yes, I include the juices in the pie. And no, the pie was not soggy. I had enough cornstarch in the pie to thicken the sweet syrup. And if you let it cool for a few hours, this halloween pie holds up incredibly well.

Bon Appétit and Happy Halloween!

Yield: serves 6-8

Jack Skellington Balsamic Cherry Pie

Jack Skellington Balsamic Cherry Pie for Halloween by FamilySpice.com

This Jack Skellington Pie is a fun and spooky way to serve up a Halloween desert. This sweet and syrupy cherry balsamic pie will tantalize your taste buds!

Prep Time 1 hour
Cook Time 1 hour
Additional Time 3 hours
Total Time 5 hours


  • 2 lbs pitted cherries, fresh or frozen
  • 3/4 cup granulated sugar
  • 3 TBS balsamic vinegar
  • 1/3 cup cornstarch
  • 1 large egg
  • 1 TBS milk
  • Sanding sugar for sprinkling on crust (optional)
  • 2 pie crust doughs, homemade or store-bought


  1. Preheat oven to 400°F/204°C.
  2. In a bowl combine cherries, sugar, vinegar and cornstarch and stir until combined. Set aside.
  3. Prepare homemade pie dough or remove store bought from refrigerator and unwrap. You want a 12-inch circle. Carefully place one dough into a 9x2 inch pie dish.
  4. Gently press dough into place with your fingers.
  5. Pour the filling into the crust, including the juices.
  6. Place the second pie dough onto a well floured surface, preferable a silicone pastry mat. Place the Jack Skeleton template in the center of the dough.
  7. Using the tip of a knife, trace the face onto the dough. Remove the paper template and use your knife to cut out the eyes and nose. Cut out the slits for the eye brows and mouth.
  8. Gently flip the pie crust over and gently place it over the pie filling, making sure the face is resting in the center of the pie. Slowly peel the silicone mat off.
  9. Using a small pairing knife, trim off any excess pie dough overhanging the pie dish. Press the edges of the two pie crusts together to seal.
  10. Fold the ends of the pie crust underneath itself to create a thick edging. To create the scalloped edge xxx.
  11. Use the tip of a sharp pairing knife to separate the slits more and accentuate the mouth and eye brows.
  12. In a small bowl whisk together egg and milk to create the egg wash.
  13. Lightly brush the top of the pie crust with the egg wash. Sprinkle the top with sanding sugar, if using.
  14. Place the pie onto a large baking sheet and bake for 20 minutes.
  15. With the pie untouched and still in the oven, turn the temperature down to 375°F/190°C and bake for an additional 30-35 minutes.
  16. If pie crust is browning too quickly, cover with pie crust shield or make one with foil.
  17. Allow the pie to cool for 3 full hours on a cooling rack at room temperature before serving. This helps the cherry filling to cool and thicken up.


Serve alone or top with whipped cream or ice cream.

Nutritional information calculated with olive oil pie crust recipe from my cookbook, Cooking Techniques and Recipes with Olive Oil.

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Nutrition Information:



Serving Size:

1 slice

Amount Per Serving: Calories: 714Total Fat: 32.3gSaturated Fat: 4.6gCholesterol: 0mgSodium: 294mgCarbohydrates: 103gFiber: 4.1gSugar: 48.2gProtein: 7.8g