[These cookies were originally posted wayyyyy back in February 2009. I wanted to revive them from the archives because they deserved some new and improved pictures, and, most importantly, because these were always a Thanksgiving tradition in our family.]
I rarely associate Thanksgiving dessert with anything other than things like pie (pumpkin, pecan, apple, oh my!), pumpkin rolls, carrot cakes and gingerbread trifles. The cookie baking tends to ramp up the week after Thanksgiving when all of the Christmas baking kicks off, but there is one cookie that will forever and always remind me of Thanksgiving… These “pillow” cookies.
In our family, they were simply referred to as pillows; I have no idea how they got that name, but I guess is that it’s because they’re little puffs of deliciousness :) These are essentially little nut rolls that have been baked and dipped in a basic powdered sugar icing. Growing up, Thanksgiving was a huge deal. All of my grandfather’s family lived outside of Chicago and many of them would travel here to Pittsburgh for the week to celebrate the holiday. The week before they showed up, my grandma made batch after batch of these cookies, on top of all the other cooking and prepping that was required for a house full of people for a week plus hosting a major holiday for well over 20 people. Somehow though, my grandma never, ever made it look like actual work. She was absolutely in her glory.
While these little nut rolls might look a little high maintenance, they really couldn’t be easier to make. If you have a food processor, the filling comes together in less than five minutes. In keeping with my grandma’s tradition, I make the dough using a hand mixer and keep the stand mixer on the shelf. After the dough and filling are made, it’s a simple process of rolling out the dough, spreading the filling and rolling it up and cutting into slices.
I always remembered my grandma’s cookies being smooth on top, but last year my mom was at my house when I was making them and said my grandma always baked them cut-side-up. No matter how I bake them, I can’t get them to look exactly like my grandma’s, but they still taste just like hers!
Since my grandma passed away, I’ve made sure that these cookies have been on my Thanksgiving dessert menu every year. It just wouldn’t be Thanksgiving without them! The best part is that whatever we don’t finish after Thanksgiving dinner can be frozen for Christmas trays.
1. Preheat the oven to 350°. Line two cookie sheets with parchment paper.
Make the Dough: In a medium bowl, whisk together the flour, baking powder and salt.
Using an electric mixer on medium speed, cream together the sugar and shortening. Add the egg and vanilla and combine well. Add in the remaining ingredients, alternating between the flour mixture and milk, starting and ending with the flour mixture and making sure all of the ingredients are well incorporated. (The dough will be soft.) Divide the dough into four even pieces, wrap each in plastic wrap, and refrigerate for at least 1 hour.
Make the Filling: In a large bowl, stir together the chopped nuts and the sugar. Add the melted butter and stir until evenly moistened. Add the egg whites and mix well until completely combined.
Assemble the Cookies: On a well-floured surface, roll out a piece of dough into a rectangle measuring about 6 inches by 18 inches. Using an offset spatula, spread one-quarter of the nut filling onto the dough, leaving a small border around the perimeter of the dough. Roll up as you would a jelly roll, with the short ends to the left and right of you, and seal the ends. Cut the roll into 1-inch pieces and place on the prepared baking sheet cut-side-up. Repeat with the remaining pieces of dough and filling (you should be able to fit all of the cookies on two baking sheets.) Bake until the cookies are a light golden brown, about 30 minutes. Transfer the cookies to a wire rack and cool completely.
Ice the Cookies: Once the cookies are cooled, whisk together the powdered sugar, vanilla and milk in a small bowl. Dip the tops of the cookies into the icing and let any excess drip off. Allow the icing to set completely before storing. The cookies can be stored in an airtight container at room temperature for up to 2 weeks. These cookies also freeze incredibly well.