Homemade Oatmeal Cream Pies
I had to save the best for last this week. Oatmeal Cream Pies were my all time favorite. There’s just something about that soft chewy oatmeal cookies with the cream filling smooshed between.
I have a confession to make about the store bought version of this cookie. When I was in High School, I was the yearbook editor senior year with a good friend of mine K. He and I had a class period each day to do yearbook work as an independent study class. We had the yearbook room to ourselves for one hour a day. It was a lot of fun. We kept Oatmeal Cream Pies in the yearbook drawer and would house these things on a regular basis. We’d go through a disgusting amount of these cookies in one hour. Thank goodness for my high-school metabolism (which has since vanished), as well as my stomach of steel. Oh man, parts of high school were a good time.
Back to reality. In the past 10+ years since then, my stomach has become more sensative to dairy and other foods, and I have to work to not gain weight. I’ve learned a lot about how to eat healthy and gained quite the love of cooking and baking. I’ve also learned that most store bought foods can be made a hundred times better at home.
These cookies are no exception. The brown sugar in the cookies keeps them perfectly soft and the filling is so much better than what’s in the store bought version. It’s like a homemade marshmallow fluff, and it’s amazing. I packaged them in celophane bags so they were easy to throw into lunches for me and Hubby this week.
One Year Ago: Best Dang Thing Ever Bars
Homemade Oatmeal Cream Pies – from How to Eat a Cupcake – makes 24 pies
Printable Recipe
Cookies
3/4 cup unsalted butter, softened
2 cups packed brown sugar
2 eggs
1/2 tsp salt
2 cups flour
1 tsp baking powder
1 tsp ground cinnamon
2 cups quick-cooking rolled oats
2 tsp baking soda
3 Tbsp boiling water
Filling
1 Tbsp plus 1 tsp unflavored gelatin (about 1 1/2 packets)
1/3 cup plus 1/4 cup water (divided)
3/4 cup sugar
1/2 cup light corn syrup
2 tsp vanilla
1 cup powdered sugar
8 ounces vegetable shortening
Make the cookies
Preheat the oven to 425 degrees F. Lightly grease a baking sheet and set aside (or use parchment).
Cream the butter, sugar, and eggs in a large bowl.
In a separate bowl, sift together the salt, flour, and baking powder. Add to the creamed mixture. Add the cinnamon and oats. Mix well.
In a small dish, add the baking soda to the boiling water, and then stir the mixture into the rest of the batter. Mix well.
Drop by the tablespoon onto the baking sheets about 2 inches apart and bake until the cookies are firm and just starting to turn golden around the edges, 10 to 15 minutes. Cool the cookies on a wire rack or a plate.
Make the filling
In a small measuring cup, sprinkle the gelatin over 1/3 cup cold water. Let stand, stirring once or twice until the gelatin softens, about 5 minutes.
In a heavy 2-quart saucepan over medium-high heat, stir together the granulated sugar, corn syrup, and 1/4 cup hot water until well blended. Continuing to stir, raise the heat to high and bring to a full boil. Continue boiling for 30 seconds. Immediately remove from the heat. Stir in the gelatin mixture until it dissolves completely.
Transfer the mixture to a large bowl. Add the vanilla.
With a mixer on medium speed, beat for 20 seconds. Gradually raise the speed to high and beat until the mixture is stiffened, white, very fluffy, and cooled to barely warm, about 5 minutes.
Reduce the mixer speed to low and gradually add the powdered sugar.
Add the shortening and beat until completely smooth.
The filling will set up as it sits, so wait until it is thick enough to spread or pipe before filling the cookies.
I am Jen the Beantown Baker. Engineer by day and baking maven by night. Hubby serves as my #1 fan and official taste tester. We got hitched back in 2006. Barefoot. In the sand. With the waves crashing behind us. It was one of the best decisions we’ve ever made. 
Oh wow, I don’t think I’ve had an oatmeal cream pie in FOREVER, but I’m sure I’d love a homemade version. Definitely adding these to the list!
Sues
I used to love those oatmeal cream cookies when I was growing up to! I haven’t had one in over ten years and this recipe brought so many memories back!
awesome! My grandparents are in town for the weekend and always have Little Debbie cream pies at their house – might have to try to whip these up this weekend because I bet they would love it!
Those things look amazing!
And i would like to give a shoot out to the One-year ago link “Best Dang Thing You Ever Tasted Bars”= the name says it all!
I’ve never one either, which is clearly why I ought to make these for myself.
i LOVE oatmeal cream pies and haven’t had one forever, but a homemade one… that’s worth trying out!
Be still my heart (it’s fluttering). This is the most satisfying cookie of all time and yours looks absolitely perfect.
These look great Jen!
These look AMAZING!!
Oh my, such a childhood favorite!!! They look fabulous!!!
Are we the same person? My senior year (in high school AND college) I was the co-yearbook editor and ate a disgusting amount of these. FYI the off-brand ones are terrible. I made that mistake during one 3am deadline. I’m definitely making these soon!!
You’ve totally made my day with this post! I’ve been searching for the perfect oatmeal cream pie recipe forever, ever since a former coworker of mine brought in her version and wouldn’t share the recipe! I’ve tried other recipes but it’s always the cream portion that ends up being different or disappointing. I can’t wait to try this recipe!
Ahh… the yearbook memories. I can’t believe how many of those we ate. If only that metabolism was still in place!
I so need to make these! I was totally obsessed with the Sara Lee oatmeal cream pies when I was in high school, and I can only imagine they are WAY better when you make them yourself! Yum.
I used to live on those pies! I used to love those things. This has been on my list to make for awhile- Everyday Food by Martha had something similar in this months magazine!
Ooooh those were a childhood lunchbox staple for me! Fun
Oh wow, I’m saving this recipe – I also used to love oatmeal cream pies!
I just made these this weekend and they are a HIT in my house! Oh, and they’re way better than the boxed kind. Thanks for sharing!
These look great! The oatmeal pies were one of my favorite Little Debbie snacks. I bet the homemade version is a million times better!
i used to love these!! i bet they’re heads and shoulders above what i remember
Definitely bookmarking these! They look amazing!
My husband might love you more than me after this. His favorite cookie is the oatmeal cream pie!
I love the Little Debbie oatmeal cream pies but after one or two you really notice how “processed” they taste. I finally had time to make these late Friday night and they came out quite yummy! They were great with coffee in the morning and we just had some for dessert at a family dinner (we’re even talking about making them for our sister-in-law’s baby shower and coloring the filling).
I do have two tips. One – make the cookies first. I had read about the filling setting as it rested, so I figured I’d do that first, but that was a mistake. By the time I was ready to fill the cookies the cream was more like marshmallow and I had to mix in some corn syrup to thin it back up. Two – keep a close eye on your first few batches of cookies until you get the timing down. My oven is low quality but predictable; however these cookies still seemed to vary batch-to-batch, with the average about 4-5 minutes. However, even the ones that were a little dark on the bottom still tasted good.
Good point Sarah – Definitely make the cookies first. They have to completely cool prior to filling them anyways.
Gah! I wish I would have read these comments before I started! Sarah – my oven was the same as yours. Five minutes per batch of cookies was plenty. I left my first batch in for over ten… oops!
Aside from the 12 cookies that went straight to the garbage can, these were INCREDIBLE. I still can’t get over how chewy they are. Thanks for the fantastic recipe!