Hoot Owl Cookies
Learn to make Hoot Owl Cookies from a vintage-inspired recipe using checkerboard sugar cookie dough, chocolate chips & almonds. Simple and cute!

- Prep time
- 2 hr
- Cook time
- 8 min
- Yield
- 48 servings
- Difficulty
- HARD
Ingredients
Quantities are shown as originally provided.
- 3 cups all purpose flour
- 1 1/4 cups granulated sugar
- 2 1/2 sticks unsalted butter, at room temperature
- 2 large egg yolks, at room temperature
- 1/4 cup whole milk, at room temperature
- 1 1/2 ounces unsweetened baking chocolate
- 1 tablespoon baking powder
- 1 1/2 teaspoons vanilla extract
- 1/2 teaspoon salt
- Large chocolate chips
- Whole almonds
Instructions
- 1
In a small saucepan, melt the baking chocolate over low heat. Once melted, remove from heat and set aside.
- 2
In a large mixing bowl, whisk together the flour, baking powder and salt. Set aside.
- 3
In a small bowl, stir the milk and vanilla together. Set aside.
- 4
In a standing mixer fit with the paddle attachment, cream together the butter and sugar until light and fluffy, about 3 minutes.Add the egg yolks and mix until just combined, about 30 seconds.
- 5
Add 1/3 of the flour mixture and mix on low speed until just combined. Then add 1/2 of the milk mixture and mix on low speed until just combined. Continue adding the remaining flour and milk mixtures, alternating between each and ending with the flour mixture. Mix until everything is incorporated and a soft dough forms.Remove 2/3 of the dough (about 1 lb 6 oz) from the mixing bowl and set aside.
- 6
Add the melted chocolate to the remaining 1/3 of dough and mix on low speed until fully incorporated and no streaks of chocolate remain. Set aside.
- 7
On a lightly floured surface, roll 1/2 of the light colored dough into a 10 x 4.5 inch strip. Set aside.
- 8
Roll 1/2 of the chocolate dough into a 10 inch log.Place the chocolate dough on top of the light colored dough.
- 9
Mold the light colored dough around the chocolate dough. Repeat steps with remaining halves of light colored and chocolate dough to create 2 rolled logs with chocolate inside.
- 10
If the ends are not evenly covered with the light colored dough, you can use a serrated knife to even them out.
- 11
Wrap the dough logs with aluminum foil. Chill for at least 2 hours.
- 12
Preheat oven to 350 degrees.Cut dough into slices about 1/8 inch thick.
- 13
Place two slices side by side. Gently press the dough in the center together so that the two cookies become one.Pinch a corner of each slice to form ears. These cookies will spread so try to exaggerate the ears a bit so that you can still see them after the cookies have baked. You can smooth any rough edges by gently tapping with your fingertips.
- 14
Place a chocolate chip in center of each eye for eyes and a whole almond between the slices for a beak.Bake for 8 – 12 minutes. Remove from baking sheets immediately and allow to cool.