Hoot Owl Cookies – A vintage-inspired recipe using checkerboard sugar cookie dough, chocolate chips & almonds. Simple and cute!
You must know by now how much I love old vintage cookbooks. When I’m in the kitchen, waiting my bread to rise or the proverbial water to boil, I often pluck a vintage recipe from my library to thumb through. Once in a while I come across a gem of an idea, something that is unique enough to make me excited. It’s the way I felt when I saw page 83 of 100 Grand National Recipes, a recipe booklet published in 1957 in conjunction with the Pillsbury’s Best 8th Grand National competition. It didn’t have a very promising cover photo, but you never know what you might find inside…
The picture of the cookies jumped out at me– adorable owl-faced cookies with nuts for beaks and chocolate chips for eyes. The recipe was submitted by a young woman named Natalie R. Riggin from Olympia, Washington, who won $5,000 and the 2nd Grand Prize of the competition for her cookies. She said:
“I am going to use the prize money I won with my cookies to complete the education of my sister and myself. I make these cookies mostly on Halloween– but my family says they’re good to eat any time.”
Sadly, often these vintage recipes don’t work quite as well as I’d like them to. In this case, I found the dough in the original recipe was too crumbly to shape– it didn’t have enough moisture. I added an extra egg, which helped, but the flavor of the cookies wasn’t quite right. It was a bit too salty and just lacked an overall “yum” factor. I also didn’t love the look of using cashews for beaks, which appeared orange in the vintage photo but baked pale cream colored in the test attempts.
My assistant Ashley and I started hunting for similar recipes that we might use to achieve the look of the Hoot Owl Cookie. We tried a few different recipes, but none of them were great– some of them spread too much, some were difficult to roll, most didn’t keep their shape. Then Ashley came across these Checkerboard Cookies on Chow.com from “Cookies: Creative Cookie Baking” by Sunset Books (now out of print). We whipped up a batch using this recipe for the dough, but used the technique of the vintage recipe to make owl faces. I also replaced the cashews with raw whole almonds, which looked more beak-like to me.
The result was utterly adorable and really tasty, too. Despite being somewhat tricky looking, they really aren’t that hard to make, so I’m hoping no “Pinterest Fails” come out of this post (nailed it!). Proceed without fear and whip up a batch for Halloween, Thanksgiving, or just because it’s autumn and why the heck not? Thanks to Natalie Riggin, wherever she might be, for this super cute seasonal cookie idea!
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- 3 cups all purpose flour
- 1 1/4 cups granulated sugar
- 2 1/2 sticks unsalted butter, at room temperature
- 2 egg yolks, at room temperature
- 1/4 cup whole milk, at room temperature
- 1 1/2 ounces unsweetened baking chocolate
- 1 tbsp baking powder
- 1 1/2 tsp vanilla extract
- 1/2 tsp salt
- Large chocolate chips
- Whole almonds
You will also need
- Standing mixer, mixing bowls, small saucepan, rolling pin, aluminum foil, sheet tray(s), silicone baking sheet or parchment
- In a small saucepan, melt the baking chocolate over low heat. Once melted, remove from heat and set aside.
- In a large mixing bowl, whisk together the flour, baking powder and salt. Set aside.
- In a small bowl, stir the milk and vanilla together. Set aside.
- 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.
- 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.
- 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.
- On a lightly floured surface, roll 1/2 of the light colored dough into a 10 x 4.5 inch strip. Set aside.
- Roll 1/2 of the chocolate dough into a 10 inch log.
- Place the chocolate dough on top of the light colored dough.
- 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.
- If the ends are not evenly covered with the light colored dough, you can use a serrated knife to even them out.
- Wrap the dough logs with aluminum foil. Chill for at least 2 hours.
- Preheat oven to 350 degrees.
- Cut dough into slices about 1/8 inch thick.
- 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.
- 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.
- Store cookies in a sealed tupperware in single layers separated by wax paper. Do not stack them directly on top of each other (I know I did in the picture, but then I regretted it!). Stacking them can cause the chocolate chip eyes to stick to the other cookies, which will mess up the look of the eyes.
- Note: Rolled dough logs can be frozen for up to a month; wrap dough logs in plastic, then tightly in aluminum foil, before freezing. Let the dough fully defrost overnight in the refrigerator before slicing and shaping the cookies.