Double Decker Pumpkin- Caramel Pie

Every year around this time, our community has a small Harvest Festival, complete with hay rides, Kettle Corn, potato sack races, bratwurst with sauerkraut, those annoying body tattoos, and a pie bake-off/chili cook-off. My son and I always enter the pie contest. It’s fun to sit around and talk about what we’d each like to bake. Usually I let the kiddo enter into the “other” pies category while I tackle a fruit pie. Competing in the same category as your child is never a good idea. This year, however, I competed. I entered a Double Decker Pumpkin- Caramel Pie.

This pie was made late at night- in anticipation for delivery to the contest the following morning, so I didn’t attempt to take step by step photos. You can imagine an Oreo crust (I used the Oreos with CHOCOLATE filling) baked for a short time and then filled with a simple pumpkin custard and baked some more. Refrigerated overnight, the caramel whipped cream layer is added the next day. Where’s the caramel? It’s melted with cream and then whipped into whipped cream to create the best-tasting whipped cream EVER.

There was of course a pie EATING contest too. Chocolate cream pie. My boy competed as the reigning champ from last year. He wasn’t able to shove the pie into his nose mouth quickly enough this year. Maybe the caramel apple, bratwurst and churro he ate prior to competing had something to do with his inability to perform.

There it is in all its glory. Chocolate shavings on top made it more purdy (since my crust was looking rather rustic-looking). Unfortunately, I did not get to take a photo of the pie when it’s cut. Will you trust me when I tell you that it’s beautiful? A chocolate crust, a pumpkin layer and then that wonderful caramel whipped cream layer too. This will most definitely be my chosen recipe for pumpkin pie this Thanksgiving.

And guess what? It took first place too! I’ve entered this darn pie contest every single year since 2004 and this is the very first time I’ve taken first prize. I’d say it’s about time. But this pie was surely worthy of taking it. I’m just glad the judges liked pumpkin pie. And that there weren’t a zillion entries 😉 My boy scored with his pie too, which he will be sharing on his blog this Thursday…

Yield: One 9-inch pie

Prep Time: 35 min + chill time

Cook Time: 45 min

Double Decker Pumpkin- Caramel Pie

This pie took first place in a local Fall Harvest Festival pie contest!


25 Oreos (creme included), crushed into crumbs (about 2 cups)
6 tablespoons unsalted butter, melted
3 large eggs
2 3/4 cups heavy cream, divided
One 15-ounce can unsweetened pumpkin puree
1/2 cup light brown sugar
1 teaspoon pumpkin pie spice
1/2 teaspoon salt
28 caramels, unwrapped
1 ounce bittersweet chocolate, for grating


1. Preheat oven to 350 degrees F. In a small bowl, stir the Oreo crumbs and butter until combined. Press the mixture onto the bottom and up the sides of a 9-inch deep-dish pie pan; freeze until set (15 minutes). Bake for 10 minutes; let cool.

2. Meanwhile in a large bowl, whisk together the 3 eggs, 1 cup cream, pumpkin, brown sugar, spice and salt until just combined. Pour into the cooled pie shell and bake until set, 40 to 45 minutes. When you shake the pan, the filling should no longer be jiggly. Let the pie cool at room temperature slightly, then refrigerate for at least 3 hours, or overnight.

3. In a bowl, microwave the caramels with 1/2 cup cream until melted, 2 to 3 minutes- adding 1 minute increments, if needed, if they are still not completely melted. Stir until smooth, then let cool to room temperature.

4. Using an electric mixer, whip the remaining 1 1/4 cups cream until soft peaks form. Drizzle in the cooled caramel and beat until well blended. Spoon the caramel whipped cream on top of the pumpkin filling and refrigerate until completely chilled. Before serving, coarsely grate the chocolate on top of the pie


*If you don't have access to Oreo's, you can use another type of chocolate sandwich cookie. I used the Oreos with the chocolate filling, but you can use the regular ones if you'd like.
*If your pie cracks on the surface while baking, don't worry about it- you'll be covering that up with the caramel whipped cream!
*Don't have any pumpkin pie spice? Make your own by mixing equal parts of cinnamon, ginger, allspice and nutmeg.
*Stick toothpicks in the top of any leftover pie before you cover with plastic wrap (keep stored in the refrigerator).

Source: (adapted from Everyday with Rachael Ray)