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.”
I made some slight modifications to the dough, using these Checkerboard Cookies from “Cookies: Creative Cookie Baking” by Sunset Books as a base (now out of print). I 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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Hoot Owl Cookies
Ingredients
- 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
NOTES
Instructions
- 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.
Nutrition
I have been making these for over 40 years with the original recipe. I’m wondering why you changed the recipe because they were really perfect as they were.
The first couple of times I tested it, I found the dough difficult to work with. The checkerboard dough was easier to mold and shape. But if the original recipe works for you, don’t mess with it! 🙂
Fantastic idea. As a 61 year old dad, who was looking for an inspirational idea for my sons 27th birthday, these were just perfect. Thank you for putting this wonderful recipe on your blog. I suspect a new family tradition has just been created here in the UK.
Hoot Owl… How Cute! My niece and nephew will love these!
I have been making these cookies since I assumed the tradition from my mom, who still has the original Pillsbury cookbook this recipe appeared in. I’ve often wondered what became of the brilliant young baker who invented these wonderful cookies that have followed me throughout my life, from all of my grade school Halloween parties to the ones when I baked them for my daughter, and to this day I continue to bake them for my co-workers and friends. My mom still has the original book! Anyway, I’ve never changed a thing about this recipe, ever, and it has served well for 3 generations now. If it ain’t broke, don’t fix it!! You go Natalie!
Patti/ Cleveland, Ohio
So very happy you have been enjoying these cookies all these years!
Such a joy to see that making these cookies is still such a happy project for moms and children, the world over.
Dear Natalie:
Thank you Thank you Thank you! I can’t tell you how much your wonderful recipe for Hoot Owl Cookies has meant to my family over the span of 3 generations! Your darling little owl faces have brought me and my family so much joy over the years. Priceless!
Patti/Cleveland OH
Thank you so very much for presenting my Hoot Owl Cookie recipe in such a delightful light and for adapting it nicely to your own requirements. Your beautiful and precise presentation makes it easy to follow the original method while obtaining the desired results. I am delighted to have found you, and am pinning your presentation of my recipe to my Pinterest account. What fun! Sincerely, Natalie Riggin Neal, 2nd Grand Prize Winner, the Pillsbury 8th Grand National Bake-off
Dear Natalie, what a hoot! So happy you found the blog, what are the odds?? Thank you for this adorable idea, it is truly creative and unique.