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.

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Homemade Oatmeal Cream Pies

Yield: 24


For the 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

For the 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.

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16 Responses to “Chocolate Whiskey and Beer Cupcakes”

  1. #
    yumventures — March 10, 2010 at 1:53 pm

    Mmmm amazing! I love all of the different flavors in each part of the recipe! Perfect for the 17th…maybe even with a drop of green food coloring =)

  2. #
    Sunshine — March 10, 2010 at 2:28 pm

    I’ve been wanting to make a version of htis for awhile and almost did this weekend. Now my plan is tackle them for St. Pat’s. Thanks for reminding me to do this.

  3. #
    Jes — March 10, 2010 at 4:33 pm

    My husband and his Army buddies LOVE these cupcakes! I get requests for them almost weekly!

  4. #
    Cara — March 10, 2010 at 4:40 pm

    sounds so good!! I could go for one now 🙂

  5. #
    nutmegnanny — March 10, 2010 at 7:48 pm

    Well I love Irish Car Bombs so in dessert form I know I would love it even more!

  6. #
    Carly — March 10, 2010 at 8:10 pm

    Wow – I am dying to try these. They look amazing!

  7. #
    Xiaolu — March 10, 2010 at 9:14 pm

    Wow these look amazing. That looks like the perfect amount of frosting, too.

  8. #
    Joanne — March 11, 2010 at 12:17 am

    I made these for a friend’s birthday last month and absolutely fell in love with them. They are the perfect St. Patty’s day cupcake. Or any day really. My friends proclaimed them the best they had ever tasted. Yours look fantastic!

  9. #
    Brisbane Baker — March 11, 2010 at 8:07 am

    What a wonderful recipe! And just in time for St Pats 😀


    Check me out.

  10. #
    Kerstin — March 12, 2010 at 3:17 am

    Mmm, they look amazing and are so perfect for St. Patty’s Day – yum!

  11. #
    Samantha Kate — March 12, 2010 at 8:17 am

    Wow these are some fancy looking cupcakes! Great job 🙂

  12. #
    Shayna — October 9, 2010 at 2:34 am

    I’m still in the process of making these…(Have yet to Ice and taste) But My ganache didn’t come out right…I stayed runny even when completely cooled and I can’t figure out what I did wrong 🙁

  13. #
    Jen — October 11, 2010 at 12:47 am

    Shayna – So sorry to hear the ganache didn’t set up. Did you try putting it in the fridge? I’ve never had that issue…

  14. #
    Richele McHenry — March 14, 2013 at 3:35 pm

    I am ready to make these but I do not have enough bittersweet chocolate for the ganache. Can I use semi-sweet or unsweetened chocolate? Will it still taste okay?

    • beantownbaker — March 16th, 2013 @ 2:49 pm

      Sorry I didn’t get back to you sooner. Semisweet would work ok, I wouldn’t use unsweetened.

  15. #
    Kristina — July 24, 2015 at 1:35 pm

    Have you ever made these into a cake? I have made them multiple times and love them but was hoping to make this into a cake for a birthday. Any thoughts?

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