I couldn’t decide which pie to bake for Pi Day, so the only logical decision I could make was to just bake and share both with you on the same day. Since this is a special day of pie feasting after all, why not embrace both options with open arms? I hope you don’t mind. That’s two pies for the price of none! The reason you’re getting two posts today is because I was having a hard time brainstorming different pies to make over the weekend and narrowing down a single choice. Whenever I thought up of a good idea, I just wrote it down. Then when I had a little list of about six or seven, I started wheedling the choices down. I thought about it for a while, crossing off the ones that didn’t quite work, and so I was left with two options. The first was this Strawberry Cream Pie and the second is this sort of crazy insane Cinnamon Roll Oatmeal Raisin Pie. Cinnamon roll pie?! What makes this a cinnamon roll pie Jonathan?! Thank you for asking! I take my normal everyday pie crust and then I treat it like a cinnamon roll dough. I roll it, I brush it with butter and I sprinkle the top completely with sugar and cinnamon. Then I roll it and chill it and slice it and press it into a pie plate. Then presto, like magic, we have a cinnamon roll pie crust. Life is good.
I have to be honest with you, this is the first time I’ve ever made or eaten an oatmeal raisin pie. Prior to this post, I actually never even knew such a thing existed. It’s like a chewy oatmeal raisin cookie meets a delicious flaky pie. The two come together to create the ultimate cookie/pie dessert. The perfect treat for Pi Day, if you ask me. I came across this flavor of pie while surfing the net, as the young kids say, and decided to jazz it up a little with rum, because rum and raisins are the best of friends. I also thought it would be the best filling option for this cinnamon roll crust, which is also another internet phenomenon. What a time to be alive.
So if you’re like me and can’t decide what pie to eat today, have no fear. Take a deep breath and just follow my advice. Go for the gold. There is no one stopping you but yourself…so quit listening to yourself and just eat all the pie you can possibly eat. All bets are off today. You have two pies to make, so you better get a move on it. These two might just be my new favorite pies. Let me know in the comments below what your favorite type of pie is! I want to know!
The first thing to do is make the crust for our cinnamon roll pie crust. We’re not making cinnamon roll dough or anything. It’s just regular pie crust. So in a large bowl, combine the flour, sugar and salt. Cut in the butter and vegetable shortening until it resembles coarse crumbs.
Add in the ice cold water, a tablespoon at a time. Stir until it comes together and forms a scraggly dough ball.
**Note: Be careful to not over-mix the dough at this stage, because then you’ll warm up the butter too much and you won’t get that flaky crust we all dream about at night.**
At this stage, we’re going to treat this like a cinnamon roll dough. So on a lightly floured work surface, roll out the dough on a lightly floured work surface in a largish rectangle. Brush the dough with melted butter and sprinkle on the brown sugar and ground cinnamon.
**Note: It doesn’t have to be perfectly shaped, so don’t spend too much time on it. Again, we want to work fast so that the butter doesn’t warm up too much.**
Roll into a tight log like you would cinnamon rolls and then wrap with plastic wrap. Chill in the fridge for at least 1 hour or overnight.
**Tip: You can make this a day in advance and keep it in the fridge or freeze it for up to 1 week.**
Slice the “cinnamon rolls” into thin slices and then arrange on the sides and bottom of a well-greased pie plate. Press the slices does to attach them each to one another and fill in the holes or gaps.
**Tip: Make sure to grease the pie plate well because if you don’t the cinnamon roll crust will get stuck an then you won’t be able to get the pie out and then you’ll cry and scream and lose it. Not good.**
Place a piece of parchment paper on top and fill with pie weights or dry beans. Bake for about 10 minutes. Remove from oven, carefully remove the beans and let the crust cool completely.
In the meantime, make the filling in the food process. Combine the flour, butter, sugar, egg, vanilla, rum, cinnamon, nutmeg and salt until smooth. Add the oats and raisins and pulse until coarsely chopped and well combined. Transfer the filling onto the cool par baked pie crust, and smooth out with a rubber spatula.
Pop back into the oven and bake until golden brown on top and a toothpick inserted in the middle comes out clean, about 35 to 40 minutes. Remove from oven and let cool completely.
**Tip: If the sides of the crust gets too brown before the filling finishes cooking, cover the sides loosely with foil.**
Okay so this isn’t winning the prettiest pie award or anything. It’s just a brown slab of a pie, BUT it’s freaking delicious so let’s look past it. One way to take away from the brownness of it all, is to top it with fresh whipped cream and cinnamon.
Beat the cream on high with a whisk with the powdered sugar and vanilla extract until soft peaks form. Slice the pie into wedges and then top with the fresh whipped cream and sprinkle with fresh ground cinnamon. Have I mentioned how much I love cinnamon?
This is one of those pies that is great warmed or even better cold right from the fridge. So if you want to warm up any leftovers, pop it in the microwave for about 10 to 15 seconds or in the oven for about 5 minutes. But if you don’t have that kind of time, eat it cold.
If you want to add even more depth and flavor to these raisins, you can simmer about 1 cup of dark spiced rum and 1/2 cup water and then pour over the raisins in a bowl. Let steep to allow the raisins to plump up, about 30 minutes. Drain and then add the raisins to the filling with the oats.
Of course, if you don’t have the time or energy to make the cinnamon roll crust, a regular crust works great. Once you make the dough, wrap in plastic and chill. Skip the whole rolling out, brushing with butter, sprinkle with sugar and roll and slice. Instead, once the crust has chilled, roll out into a circle and then place into a pie plate. Trim the edges and then crimp. Either crust option would be great.
- 1¾ cups all-purpose flour
- 2 teaspoons granulated sugar
- pinch of kosher salt
- 6 tablespoons unsalted butter, cold and diced
- 4 tablespoons vegetable shortening
- 5 to 6 tablespoons ice water
- 3 tablespoons unsalted butter, melted
- ⅓ cup packed light brown sugar
- ½ teaspoon ground cinnamon
- 1 tablespoon all-purpose flour
- ¾ cup packed light brown sugar
- 10 tablespoons unsalted butter, softened
- 1 large egg
- 2 teaspoons vanilla extract
- 2 teaspoons dark rum (optional)
- 1 teaspoon ground cinnamon
- ½ teaspoon freshly ground nutmeg
- ¼ teaspoon salt
- 1 cup old fashioned oats
- 1 cup raisins
- 1 cup heavy cream
- 2 tablespoons powdered sugar
- ½ teaspoon vanilla extract
- pinch ground cinnamon
- To make the pie crust, In a large bowl combine the flour, sugar and salt. Add the cold diced butter and rub with your fingers (or a pastry blender) until coarse crumbs form. Add the vegetable shortening and rub with your fingers (or pastry blender) as well, until the mixture resembles coarse crumbs the size of peas. Add the ice water, 1 tablespoon at a time, mixing until the dough comes together. It should be slightly sticky. Dump out onto a lightly floured work surface and roll into a large rectangle, about ¼-inch thick. Brush with melted butter and sprinkle with brown sugar and cinnamon. Starting with the longest side, roll into a tight log like you would an actual cinnamon roll dough. Cover with plastic wrap and chill for at least 1 hour or overnight.
- Preheat oven to 350 degrees F. Grease a 9-inch pie plate with cooking spray or butter. Slice the cinnamon roll log into thin (1/4-inch) slices and arrange on the sides and bottom of the pie plate. Press the slices down to attach them to each other and close off any holes or gaps. Cover with parchment paper and fill with pie weights or dried beans. Bake for about 15 minutes. Remove from oven and carefully remove the paper and beans. Set aside.
- To make the filling, in the bowl of a food processor, combine the flour, sugar, butter, egg, vanilla, rum, cinnamon, nutmeg, and salt until smooth. Add the oats and raisins and pulse a few times until coarsely chopped. Transfer the filling onto the crust and smooth out with a rubber spatula. Bake until golden brown on top and the center is no longer jiggly, about 35 to 40 minutes. (If the sides of the crust is getting too brown before the filling is done, cover the sides with foil). Remove from the oven and let cool completely on a wire rack.
- To make the whipped cream, beat the cream, powdered sugar and vanilla on high until soft peaks form. Cut and serve the pie with a dollop of fresh cream. Pie can be kept in the fridge for up to 3 days.