Arguing is just part of the fabric of Thanksgiving – literally. Watch this Tasting History with Max Miller video where he explains how Thanksgiving started a plea for unity from Sarah Josepha Hale, only for everyone to be like “lol no” but take her holiday idea anyway. Typical.
In the Before Times, polarizing moments at Thanksgiving included debates like the preference of canned or homemade cranberry sauce, the presence of marshmallows on sweet potato casserole, if the first glass of wine even counts, and…whether anyone actually likes pumpkin pie.
This recipe is for people who don’t like pumpkin pie.
At first, the chocolate almost masks the pumpkin entirely. Then the pumpkin flavor comes in, still not overwhelming, but just right. Rob and I ate a slice and a half each as soon as we reasonably could.
Triple Chocolate Pumpkin Pie Teachable Moments
- Lesson #1: This is an adaptation of a recipe originally from Martha Stewart, everyone’s favorite white collar criminal. Her recipe, which is no longer on her website which resulted in me finding a PDF of it I sent to my cousin A DECADE AGO, included instructions for making the graham cracker crust from scratch.
I tried that, and the existential crisis that ensued as I tried to spread chocolate on a crumbly, barely-put-together crust resulted in Rob wordlessly leaving for the grocery store and coming back with a premade graham cracker crust like the goddamn hero that he is.
Trust me, we were all better off for it.

- Lesson #2: The recipe makes a LOT of filling. Enough to fill two 9″ pie crusts perfectly, or, if such a thing exists, possibly a 10″ pie crust? I tried the former and it works perfectly. Serve up double the deliciousness!
- Lesson #3: This benefits from more refrigeration. You’ll be tempted to eat it right at the 8-hour mark. DON’T. Definitely give yourself an overnight fridge situation so the flavors can sit together more and become more dynamic. Then, eat all the leftovers…if there are any.
Happy Thanksgiving and thank you all for indulging my very stupid hobby that I love so much.
Triple Chocolate Pumpkin Pie
Much like Scully and Mulder, an unlikely pair makes a great team. Who knew chocolate and pumpkin go together so well?
Ingredients
- 2 9-inch premade graham cracker pie crusts
- 6ish ounces bittersweet chocolate
- 6 oz (3/4 C) semisweet chocolate morsels
- 4 TBSP unsalted butter, room temperature
- 1 can (15 oz) pumpkin puree
- 1 can (12 oz) evaporated milk
- 3/4 C packed light brown sugar
- 3 large eggs, room temperature
- 1.5 TBSP cornstarch
- 1 tsp vanilla extract
- 1 tsp kosher salt
- 1 tsp ground cinnamon
- 3/4 tsp ground ginger
- 1/4 tsp ground nutmeg
- Pinch of ground cloves
- 1/4 C milk chocolate morsels
Instructions
- Preheat the oven to 325 degrees.
- Melt the bittersweet chocolate in a microwave on “defrost” level of heat for 30 seconds at a time. Stir between each interval.
- When the chocolate is sufficiently melted and spreadable, scoop half onto each pie crust and spread it on the bottom and up the sides.
- Use a medium bowl and whisk together the pumpkin, milk, brown sugar, eggs, cornstarch, vanilla, salt, cinnamon, ginger, nutmeg, and a pinch of cloves. Set aside.
- Melt the butter and semisweet chocolate together in a large bowl. I recommend using this double boiler method because you add the rest of the ingredients into this bowl in just a minute. Once the chocolate and butter are melted together, remove the bowl from over the heat.
- Slowly pour the pumpkin mixture into the bowl with the chocolate, whisking as you go to make sure everything is incorporated.
- Put the pie crusts onto a rimmed baking sheet, and pour pumpkin mixture into the crusts, dividing evenly between them.
- Bake until the center is set but still just a bit wobbly, 50-55 minutes (yours may need a little longer – please read any and all posts I’ve made about my shitty, temperamental oven). Let cool in pie dish on a wire rack.
- Refrigerate the pie until well chilled, at least 8 hours, but preferably overnight.
- Before serving, melt the milk chocolate in the microwave on ‘defrost” in 30 second intervals and then drizzle melted milk chocolate on top of each pie. Serve immediately.
Make the filling:
Notes
A few things:
- If you want this to be a little more pumpkin-y, take out a tablespoon or two of chocolate. However, we noticed that after a longer period of refrigeration, the pumpkin flavor was a lot more pronounced.
- This recipe yields enough filling for two 9″ pie crusts as long as you don't completely overflow them!

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