Cinderella Pumpkin Pie with Chocolate Cookie Crust

A simple, press-in cookie crust gets topped with rich and creamy pumpkin pie filling for an easy and delicious holiday dessert. Or take it to the (literal) next level with a pumpkin cheesecake centre. Both recipe options available!

Anna Olson’s latest Book, Set For the Holidays, is a seasonal gem dedicated entirely to holiday-focused food, from starters to sweets, brunches to party bites, to the masterful meals and treasured desserts that will grace your dinner table. The focus is on classic, elegant recipes that tend to be favoured during the holidays, but includes a selection you’ll find yourself turning to regularly during the frightfully long winter months.

The pumpkin seed multigrain bread will have you settling in for a cozy weekend project, the brussels sprouts with lemon and asiago would be lovely during any weeknight winter meal, the chickpea and cauliflower curry and the roasted squash and tomato bowl with white beans, spinach, and olives feel warm and satisfying after a long day, the spiced holiday granola–though its name might be deceiving–is really adaptable for year-round breakfasts and snacking, and lastly, the ham and split-pea soup sounds like everything a cold Sunday afternoon should feel like.

There’s even a section for post-holidays that focuses on using up leftovers and eating a little lighter (hello turkey cabbage roll soup!).

But Anna has her priorities straight; more than half the book is dedicated to baking. And if you’re a person who likes to bake and/or participate in a cookie exchange this time of year, there’s a robust section just for you.

My cookie interests fall primarily onto 3 recipes: the chocolate coconut oatmeal chews (basically all of my favourite things in one), the gingerbread crinkle cookies, and the carrot cake sandwich cookies. But after all that, perhaps the things I’m most excited to make are the panettone (an enriched Italian bread flavoured with rum, citrus, and dried fruit), the hazelnut orange panforte (a candy-like fruitcake that is loaded with toasted hazelnuts and all the best dried fruits–this is coming from a fruitcake hater, for the record), this cinderella cheesecake pumpkin pie, and the chocolate-glazed baked pumpkin doughnuts.

I was even thinking of baking some up for my daughter’s daycare teachers with a note that says, “I doughnut know what we’d do without you!” Cheesy or great? You tell me!

Even though I swore this would be my last pumpkin recipe of the season, I chose to feature the Cinderella Pumpkin Pie today because, like many of you, pumpkin pie is a favourite at the holiday table.

Anna calls it a “Cinderella” pie because it is a traditional pumpkin pie that has “undergone a transformation. A chocolate crust holds a pumpkin cheesecake layer topped with pumpkin pie filling. The result is a grand two-tiered pumpkin dessert that feeds twice as many people as a regular pumpkin pie.”

I’m a sucker for a well-made pie dough (I appreciate it more than the filling), but the thick chocolate crust was really calling my name this time around. And unlike most of the world, I’m not a big cheesecake fan. (I know, I know!) So I opted to just make the classic filling.

The results were spectacular (even if they were over baked. See my notes in the recipe section to avoid this yourself.), but I’ve included both recipe options below so you can take your pick.

To nab your own copy of Set for the Holidays, head on over to our Instagram feed and leave a comment on our post. *This giveaway is now closed.*

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Yield: 12-16 slices

Cinderella Pumpkin Pie with Chocolate Cookie Crust

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This pie is so named because it is a classic pumpkin pie that has undergone a transformation. A chocolate crust holds a pumpkin cheesecake layer topped with a pumpkin pie filling. The result is a grand two-tiered pumpkin dessert that feeds twice as many people as a regular pumpkin pie. Start this pie the day before you plan to serve it so it has time to set up overnight.

Prep Time 40 minutes

Cook Time 1 hour 40 minutes

Total Time 2 hours 20 minutes

Ingredients

CRUST

• 2 ¾ cups (390 g) chocolate cookie crumbs (gluten-free, if preferred)
• 2 Tbsp (25 g) packed light brown sugar (I omitted this)
• ½ tsp ground cinnamon
• ½ cup (115 g) unsalted butter, melted
• CHEESE CAKE  LAYER (I omitted this layer for this post, but I'm sure it would be delicious.)

cream cheese filling

• 1 pkg (8 oz/250 g) cream cheese, at room temperature
• ⅓ cup (70 g) granulated sugar
• 1 tsp ground cinnamon
• ¼ tsp ground cloves
• ¼  tsp ground nutmeg
• 1 large egg, at room temperature
• ½ cup (125 mL) pure pumpkin purée

PUMPKIN PIE LAYER

• 2 cups (500 mL) pure pumpkin purée
• ½ cup (100 g) packed light brown sugar
• ½ cup (100 g) granulated sugar
• 1 tsp ground cinnamon
• ¼ tsp ground cloves
• ¼ tsp ground nutmeg
• 3 large eggs, at room temperature
• 1 cup (250 mL) whipping cream (I used 3.25% milk)
• Sweetened whipped cream, for décor (optional) (I used unsweetened whipped cream because I found the pie plenty sweet enough.

Instructions

1. Preheat the oven to 350°F (180°C) and grease a 9-inch (23 cm) springform pan. (I used a fluted tart pan.)
2. For the crust, stir the cookie crumbs with the brown sugar and cinnamon and then stir in the melted butter until evenly combined. Press into the bottom and all the way up the sides of the pan. Bake for 10 minutes (no change will be noticeable). Let cool on a wire rack while you make the filling. Leave the oven on.
3. For the cheesecake layer, beat the cream cheese until smooth (by hand is easy enough) and then beat in the sugar, cinnamon, cloves and nutmeg. Switch to a whisk and whisk in the egg, followed by the pumpkin purée. I omitted this layer. If you're following suit, jump to #5.
4. Scrape the batter into the cooled crust and bake for 30 minutes, until the cheesecake no longer jiggles in the centre. While it bakes, prepare the pumpkin pie layer.
5. Whisk the pumpkin purée with both sugars and then whisk in the cinnamon, cloves, and nutmeg. Whisk in the eggs and then the 1 cup (250 mL) whipping cream (I substituted milk). Once the cheesecake layer has baked for 30 minutes, remove the pan from the oven and gently pour the pumpkin pie filling over the cheesecake—it will fill the pan right to the top.
6. Return the pan to the oven and bake for 50 to 60 minutes more, until only the centre of the pie shows signs of jiggling. Let cool in the pan on a wire rack to room temperature, up to 4 hours. Chill the cooled pie, uncovered, in the fridge overnight to set the filling.
7. If you wish to decorate the pie, remove it from the pan and carefully slide it onto a cake stand or a platter. Scoop the whipped cream into a piping bag fitted with a plain or star tip and pipe a crown just around the top of the pie or simply dollop the whipped cream in the centre. Chill until ready to serve.

Notes

• I modified the recipe, including eliminating the cheesecake layer, reducing the sugar, and swapping in milk for cream. I have not tried this, but I suspect that non-dairy milk would substitute well here, too.
• My notes are included in the original recipe. If you are making the full recipe, be sure to use a 9-inch (23 cm) springform pan.
• You can make this pie a full day ahead of serving. Store it, uncovered, in the springform pan in the fridge overnight. Once the pie has been sliced, press a little plastic wrap or parchment paper onto the cut edges and refrigerate for up to 3 days.
• For a glassy pumpkin pie look, don't over bake it like I did! :) I was upstairs with my daughter and didn't hear my timer go off. As a result, the pie developed cracks and craters. It's still delicious, it just doesn't have that beautiful glassy top. To keep your pie from cracking, have a read through these tips.

Nutrition Information:

Yield:

16

Serving Size:

1
Amount Per Serving: Calories: 123Total Fat: 7gSaturated Fat: 3gTrans Fat: 0gUnsaturated Fat: 3gCholesterol: 56mgSodium: 101mgCarbohydrates: 13gFiber: 2gSugar: 7gProtein: 3g

This is an approximation of the nutrition offered in this recipe, and is created using a nutrition calculator.