Oatmeal Sandwich Cookies with Rum Raisin Filling

My brother and his lovely wife host Thanksgiving dinner for our noisy lovable family — God bless him — and every year I beg him for a little assignment, just so I can hold my head up. I mean, what self-respecting food blogger would sail through Thanksgiving without, um…cooking something? So this year he asked me to bring a dessert, which aside from bacon is my favorite thing to make in the kitchen. I knew my sister-in-law would be making her scrumptious and classic pumpkin pie, so I wanted to make something that would be a little different, but still sort of holiday-ish.

Then as luck would have it, my Southern husband brought home a copy of the 2009 edition of CHRISTMAS WITH SOUTHERN LIVING. And along with a variety of other recipes that I just might try over the holidays, it included this recipe for oatmeal sandwich cookies that are held together with a rum raisin cream filling. Now, I know my dad is a serious rum raisin fan, and the Southern husband is a big oatmeal cookie fan, and so it all seemed like fate to me.

Now I should warn you that these cookies are serious cookies. They are LARGE cookies. They are actually TWO large cookies stuffed with 3 tablespoons each of rum raisin filling. You could eat one today and not be hungry again until next Tuesday. But man! they are good. And Thanksgiving…heck, the whole holiday season…is when you are supposed to cut loose and eat giant rum-stuffed cookies? Right? Right. So go make them…you know you want to.


Oatmeal Sandwich Cookies with Rum Raisin Filling
  • ½ cup softened butter
  • ½ cup shortening
  • ¼ cup light corn syrup
  • 1¼ cups brown sugar
  • 1 large egg
  • 1 teaspoon almond extract
  • 1½ cups flour
  • 1 teaspoon baking soda
  • 1 teaspoon cinnamon
  • ½ teaspoon salt
  • ½ teaspoon ground cloves
  • 2 cups regular uncooked oats
  • ¾ cups chopped pecans
  • 1 3 oz package cream cheese, softened
  • 1 tablespoon milk
  • 2 tablespoons dark rum
  • ¾ teaspoon vanilla
  • ⅛ teaspoon salt
  • 1 1pound package confectioner's sugar
  • 1½ cups raisins
  1. Preheat oven to 375.
  2. Beat butter, shortening, corn syrup and sugar on medium speed until fluffy. Add egg and almond extract and beat until blended
  3. Combine flour, baking soda, cinnamon, salt and cloves and gradually add to butter mixture. Stir in oats and pecans.
  4. Shape dough into 1½ inch balls and place 2 inches apart on parchment lined baking sheets. Press down on each ball to flatten slightly.
  5. Bake for 10-12 minutes until golden. Cool on baking sheet for 3 minutes, then remove to wire rack and cool completely.
  6. While cookies are cooling, make rum raisin filling. Beat cream cheese at medium speed until creamy Add milk, rum, vanilla and salt and beat until blended
  7. Gradually add powdered sugar, beating at low speed until completely combined. Stir in raisins.
  8. Spread 2-3 tablespoons of filling on cookie bottom and sandwich with another cookie. Repeat until all cookies are used.
  9. Close your eyes, take a bite and smile a really, really big smile.


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  1. Anu says

    OMG, this is seriously my favorite food blog. The amazing recipes just keep on coming. Thank you for posting. Printing now! :)

  2. Kate Morgan Jackson says

    Thanks guys!! I am seriously considering making these again for Christmas. Well okay — for me to have in the house, but Christmas is a great excuse. :-)

  3. megan says

    I made your cookie recipe! We're not rum raisin fans in our house, so I made them with a traditional buttercream filling. they taste just like oatmeal creme pies! Great recipe, thanks. Oh, and I posted about them on my blog :)

  4. Anonymous says

    Thank you for this recipe. I look forward to tasting them. They remind me of this delicious treat I could find only for a little while at Whole Foods in Union Square – I would dream about those sandwiches.

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