Let’s talk cookies, shall we? I’ve been a cookie girl all my life. Chocolate chip cookies, gingersnap molasses cookies, and, of course, oatmeal cookies. Always chewy, never crunchy, and in the case of oatmeal cookies, always studded with tons of raisins.
But let’s go one step further. There is that amazing thing where you dollop fluffy frosting on the underside of one cookie, and sandwich it with another…. what’s that called again? Oh right, whoopie pies.
I just LOVE whoopie pies, because they’re basically like eating cookies and cake all in one. Plus, they’re just so fun to put together. Not to mention they’re weirdly easy to whip up on a weeknight. Of course, when coming up with this oatmeal whoopie pie recipe, I knew I couldn’t use just any old buttercream. Cream cheese frosting was the only way to go. It acts as a perfect slightly tangy balance to the warm cinnamon notes in the oatmeal cookies.
Speaking of cream cheese, my sister just reminded me of something my mom used to make for us: cream cheese and jelly sandwiches. Please tell me I’m not the only one who ate those growing up? Seriously so good.
Tangent over. So whoopie pies. Oatmeal raisin cookie whoopie pies.
Just… enjoy this whoopie pie recipe. 🙂
How to make whoopie pies perfectly every time
Whoopie pies look complicated to make, but they’re as simple as making a batch of cookies and slathering them with frosting. To make this oatmeal whoopie pie recipe, you’ll first need to make the chewy oatmeal raisin cookies. When making the homemade oatmeal raisin cookies, be sure that you’re using old fashioned oats and not steel cut or any other variety. Old fashioned oats give these oatmeal whoopie pies a delightfully chewy texture and bake up nicely.
You’ll also need to under bake the cookies slightly. They should still be fairly pale when you take them out of the oven (this will make the whoopie pies extra soft!). Let the oatmeal raisin cookies cool completely before frosting them. If you try to add the cream cheese frosting while the cookies are still warm, your whoopie pies will ooze and won’t look as nice.
While the cookies are cooling, make the cream cheese frosting. When making frosting, it’s crucial that you’re using room temperature butter and cream cheese. If either of these ingredients is too hard, the frosting won’t whip up properly and won’t become light and airy.
Whip the butter and cream cheese for a good two minutes with an electric or stand mixer (the mixture should turn slightly pale in color and should become fluffy). Add in the powdered sugar and vanilla extract and beat for another minute. If the frosting is too thick, you can add in a tablespoon of milk to loosen it up slightly.
Besides that, this whoopie pie recipe is insanely easy to make. These oatmeal whoopie pies always go over well with a crowd and keep well for a few days in an air-tight container.
Preheat oven to 350°F. Line 2 large baking sheets with parchment paper and set aside.
In a standing mixer with a paddle attachment, cream the butter and both sugars until fluffy, about 1 minute. Beat in the egg, vanilla extract, and salt, and mix to combine.
Remove from mixer and fold in flour, baking soda, and old fashioned oats. Once combined, fold in raisins.
Scoop dough into 1-inch balls, rolling between your hands to make them perfectly circle. Place on prepared baking sheets, leaving 1.5 inches between each cookie.
Bake for 11-12 minutes. Cookies will look underdone and still pale, but this is what you want! Allow to cool on baking sheets for 10 minutes before transferring to wire racks to cool completely.
To make the frosting, combine cream cheese and butter in a standing mixer and cream until light and fluffy, about 2 minutes. Add in powdered sugar and vanilla extract and whip for an additional 30 seconds. If it’s too dry, add in 1 tablespoon of milk.
Assemble the cookies by piping 2-3 tablespoons of frosting on the flat side of one cookie, then sandwich with another cookie! Repeat with remaining cookies.