Soft, chewy, and layered with fluffy vanilla filling, these Homemade Oatmeal Cream Pies taste like a homemade version of the classic treat you loved growing up.
Whisk together the flour and milk in a small saucepan placed over medium heat. Whisk continuously until the mixture starts to thicken—watch it closely so it doesn’t overcook. Let it cook for a couple of minutes, until the mixture has the consistency of pudding. Remove from heat, whisk out all clumps, and place in the refrigerator to cool completely. The mixture must be chilled all the way through before adding it to the butter, or it will melt it.
In the bowl of a stand mixer, beat the butter, sugar, vanilla, and salt for 2 minutes on medium-high speed, using the whisk attachment. Add the flour and milk mixture. Beat on high for 6–8 minutes until the mixture is light and fluffy (and slightly resembles whipped cream). Chill in the refrigerator until needed.
For the Pies
Preheat the oven to 350 degrees Fahrenheit (177 degrees Celsius). Line baking sheets with parchment paper or a Silpat mat, set aside.
In the bowl of a stand mixer, beat the butter, sugars, molasses, vanilla, and eggs until creamy, about 2 minutes.
In a small bowl, whisk together the flour, oats, salt, baking soda, cinnamon, and nutmeg. With the mixer on low speed, gradually add the dry mixture to the creamed mixture. Once incorporated, remove and place the dough into the refrigerator to chill for 30 minutes.
Scoop dough using a standard-size scoop (I use a #20 cookie scoop, which holds about 3 tablespoons of dough) onto prepared baking sheets. Bake for 10–12 minutes, or until the cookies begin to brown around the edges—they will look moist in the center, so don’t overcook.
Remove from the oven and let cool on the sheet for 2–3 minutes, then transfer to a wire rack to finish cooling (10 minutes or so).
Use a knife or piping bag to spread the cooled filling on the flat side of one cookie, then press a second cookie on top. Continue until the remaining cookies and filling are gone.
Notes
I like these cookies even more after they’ve rested overnight—the flavor deepens once the cookies have been sandwiched with the filling.STORE leftover oatmeal creme pies in an airtight container in the fridge for up to 3 days. Let them sit at room temperature before serving so the filling softens and the cookies aren’t too firm.To FREEZE, wrap each assembled pie in plastic wrap, then place them all in a freezer-safe bag or container. They’ll keep for up to 3 months. When ready to eat, let them thaw at room temperature for about 20 minutes.