Incredible Gingerbread Oatmeal Cream Pies

Amazing oatmeal cream pies with a gingerbread twist! These perfectly spiced gingerbread oatmeal cookies are sandwiched together with a delicious thick cream filling for the ultimate holiday cookie sandwich.
I’m sitting here watching old episodes of Grey’s Anatomy while Milly is cuddling on my lap. I just ate a slice of toast with peanut butter, banana and cinnamon…. and yesterday I officially became 36 weeks pregnant. Whew!

Surprisingly, I haven’t really craved anything sweet on a regular basis during my pregnancy. However, these gingerbread oatmeal cookie sandwiches changed EVERYTHING. I couldn’t stop eating them, or thinking about them and neither could Tony. They just scream all things Christmas!

Amazing oatmeal cream pies with a gingerbread twist! These perfectly spiced gingerbread oatmeal cookies are sandwiched together with a delicious thick cream filling for the ultimate holiday cookie sandwich.

Ingredients
Wet ingredients:
½ cup butter, at room temperature
1 cup packed brown sugar (dark is great, but light also works!)
1/4 cup blackstrap molasses
1 egg
1 teaspoon vanilla extract
Dry ingredients:
1 1/2 cups all-purpose flour
3/4 cup old fashioned rolled oats
1/2 teaspoon baking soda
1 ½ teaspoons ground ginger
1 teaspoon cinnamon
1 teaspoon allspice
1/4 teaspoon salt
For cream pie middle:
¾ cup butter, at room temperature
1 ½ cups powdered sugar
3/4 teaspoon vanilla extract
1-2 teaspoons milk to make the filling creamy

Instructions
Add room temperature butter and brown sugar to the bowl of an electric mixer and beat the butter and sugar together for 1 minute. Next, add in the molasses, egg and vanilla and beat again until well combined, smooth and creamy, about 1 more minute.
In a large bowl, whisk together the dry ingredients: flour, oats, baking soda, ginger, cinnamon, allspice and salt in a bowl. Slowly add dry ingredients to the wet ingredients and mix on low-speed just until combined. Chill dough in fridge for 1 hour, this is so the cookies have the perfect texture, so please don’t skip the chilling of the dough!

Once ready to bake cookies, preheat the oven to 350 degrees F and line a baking sheet with parchment paper. Use your hands or a tablespoon to grab a large tablespoonful of dough and roll into a ball. Place dough balls 2-inches apart on cookie sheet. Bake 9-12 minutes. If you like cookies with a crispy edges, bake for about 12 minutes. If you like softer cookies, bake for 9-10 minutes.

Remove from oven and cool the cookies on sheets about 5 minutes then transfer to a wire rack. They will still remain soft on the inside. Repeat with remaining dough. Makes about 30 cookies total (or what will be 15 cookie sandwiches).
Once cookies have completely cooled, you can make the filling: Add the room temperature butter, powdered sugar, vanilla extract and milk to the bowl of an electric mixer. Beat on low, then gradually increase speed to high for about 1 minute, or until the frosting is smooth and creamy.
Top one cookie sandwich with a spoonful of filling, leaving a nice edge around the cookies and top with another cookie sandwich, then very gently press down slightly. Repeat with all cookies. You should get about 15 oatmeal cream pies. The filling will have the best texture after letting the cookies sit at room temperature for 1 hour, if you try to bite into them earlier the frosting won’t be as firm as we’d like.