All Jacked Up

Gather ’round the campfire and pull your loved ones in close. It’s time for a ghost story more haunting than the Winchester Mystery House, more frightful than Frankenstein, and more bewitching than the lovely ladies of Salem. I’m talking about the tale of Stingy Jack.

Naysayers may call it a myth, but legend has it that Stingy Jack was a classic con artist, scraping by on someone else’s dollar while swindling his way into another man’s coin purse. He was already a man on the fringes of society, making more enemies than friends, so it should come as no surprise that eventually, the only creature willing to share a drink was the Devil himself. When last call came, predictably, Jack didn’t have the means to pay for his drink, so he made a dangerous bet with the devil instead.

Calling out his demonic power or lack thereof, he suggested that there was no way the devil could turn himself into the necessary coinage. With enough taunting and cajoling, already somewhat tipsy himself, Satan proved his prowess, transforming into a gleaming golden coin without any difficulty. Snapping up the opportunity along with the cash, Jack decided to ditch the bill and keep the money instead. Securing it in his pocket next to a silver cross, the Devil was prevented from transforming back into his original form.

Only when Jack died was demon freed, and quite peeved, to put it lightly. Hell was too good for this malicious man, so he set him off into the night, with only a piece of burning coal to light his way. Jack put the coal into a carved-out turnip and has been roaming the Earth with ever since. Somewhere along the line, repeated reiteration of the story turned the turnip into a pumpkin, and that’s how we ended up with Jack-o’-lanterns.

Mea culpa; perhaps that was more of history lesson than a horror story. I can’t help but find myself enchanted by the origins of our strange holiday traditions. If you made it this far through my rambling tale, though, you definitely deserve a drink. How about a shot of applejack, on the rocks?

Better yet, let’s put it in the pumpkin.

That, my friends is the TRUE history of how the Applejack-O’-Lantern Pie came to be.

Cradled in a flaky pastry crust lies a layer of spiked and spiced apple filling, topped by a creamy pumpkin custard. Tender fruit mingles with brown sugar-infused pumpkin puree; each bite is highly spirited, in all meanings of the word. It’s a sinfully good treat to commemorate villainous old Stingy Jack… Just don’t make any deals with the Devil to secure a second slice.

Yield: Makes 8 - 12 Servings

Applejack-O'-Lantern Pumpkin Pie

Applejack-O'-Lantern Pumpkin Pie

Boo! Don't be afraid of what lurks beneath the layer of pumpkin pie here... It's just apples simmered in brown sugar and warming spices!

Prep Time 40 minutes
Cook Time 1 hour
Total Time 1 hour 40 minutes


Apple Filling:

  • 2 Tablespoons Vegan Butter or Coconut Oil
  • 1 Pound Sweet Red Apples, Such as Fuji, Braeburn, or Envy, Peeled, Cored and Sliced
  • 1/2 Cup Light Brown Sugar, Firmly Packed
  • 1 1/2 Tablespoons Tapioca Starch
  • 1/2 Teaspoon Ground Cinnamon
  • 1/8 Teaspoon Salt
  • 1/4 Cup Applejack or Calvados

Pumpkin Filling:

  • 1 (15-Ounce) Can Pumpkin Puree
  • 1/2 Cup Unsweetened Applesauce
  • 3/4 Cup Dark Brown sugar
  • 2 Tablespoons Tapioca Starch
  • 1 Teaspoon Ground Cinnamon
  • 1/4 Teaspoon Nutmeg
  • 1/4 Teaspoon Allspice
  • 1/8 Teaspoon Salt
  • 1 Teaspoon Vanilla Extract

To Assemble:


    1. Set a medium skillet over moderate heat. Melt the butter or coconut oil and add in the apples. Stir in the brown sugar, and once bubbling, turn down the heat to medium-low. Whisk together the tapioca starch, cinnamon, and salt in a small dish before sprinkling the mixture evenly over the fruit. Mix well to incorporate smoothly, without any lumps. Slowly drizzle in the applejack or calvados, and bring to a gentle simmer. Cook for about 8 - 10 minutes, until the apples are tender and the sauce has thickened. Turn off the heat and let cool.
    2. Start preheating your oven to 350 degrees.
    3. For the pumpkin filling, whisk together the pumpkin puree, applesauce, brown sugar, tapioca starch, cinnamon, nutmeg, allspice, salt, and vanilla. Once smooth, set aside.
    4. Roll out one of the pie crusts to about 1/8th of an inch in thickness on a lightly floured surface. Transfer to a deep dish 9-inch round pie pan and smooth it into the bottom. Trim away any excess overhanging the lip of the pan. Flute or crimp with a fork, if desired.
    5. Transfer the apple filling to the prepared pie crust and smooth it into an even layer on the bottom. Gently spoon the pumpkin filling on top, carefully covering all of the apples and using a spatula to smooth the surface.
    6. Roll out the second pie crust to 1/8th of an inch thick and cut out a jack-o'-lantern face, or any other design you prefer. Apply to the top of the pie.
    7. Bake for 55 - 60 minutes in the center of the oven, until the crust is golden brown and the filling begins to bubble up around the edges.
    8. Cool completely and serve either warm, or chilled for cleaner slices.


You can free-hand a jack-o'-lantern face or download a template here.

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Nutrition Information:



Serving Size:


Amount Per Serving: Calories: 150Total Fat: 3gSaturated Fat: 2gTrans Fat: 0gUnsaturated Fat: 1gCholesterol: 5mgSodium: 65mgCarbohydrates: 31gFiber: 2gSugar: 26gProtein: 0g

All nutritional information presented within this site are intended for informational purposes only. I am not a certified nutritionist and any nutritional information on should only be used as a general guideline. This information is provided as a courtesy and there is no guarantee that the information will be completely accurate. Even though I try to provide accurate nutritional information to the best of my ability, these figures should still be considered estimations.

4 thoughts on “All Jacked Up

  1. This sounds like the best part of Halloween to me, Hannah. Yum! Not sure there’s tapioca starch anywhere, though. I found that minute tapioca, which I wanted for a Crockpot recipe, is not to be found anywhere. I did see tapioca flour, but evidently Covid pie baking is causing the shortages.


    1. That’s crazy! There are so many random micro-shortages that one could never predict. For what it’s worth, you could also use potato starch, if that’s easier to find. Good luck out there!

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