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I was told today that my cookies taste like Halloween. What a honor! I made these cookies around this time last year (pre-blog times) for my law school friends and this was a huge hit. Every party I had, people always requested these. The cookies turn out to be soft and chewy with almost a cake like center. Usually, I’m not a big fan of chewy cookies (Chips Ahoy chewy being the biggest disappointment). For some reason, the dipping of a cookie into milk and making it soft and gooey is my favorite part. And few things taste better than a mixture of pumpkin and milk. Keep reading for the recipe.


Total Time: 40 minutes         Cook Time: 10-13 minutes         Makes: 40 cookies


2½ cups of All-Purpose Flour

1 teaspoon of Baking Soda

1 teaspoon of Baking Powder

1 teaspoon of Cinnamon

½ teaspoon of Nutmeg

½ teaspoon of Salt

1½ cups of Sugar

1 cup of Unsalted Butter

1 cup canned Pumpkin (I prefer Libby’s but any kind will work)

1 Egg

1 teaspoon of Vanilla


2 cups of Powdered Sugar

3 tablespoons of Milk

1 tablespoon of Unsalted Butter (melted)

1 teaspoon of Vanilla Extract

(1) Preheat oven to 325 degrees. Combine flour, baking soda, baking powder, cinnamon, nutmeg and salt in a medium sized bowl.

(2) Beat the butter and sugar in a large bowl until well blended and fluffy. Beat in the pumpkin, egg and vanilla extract one at a time until smooth. Gradually beat in the flour mixture.

(3) Place small dollops of the cookie dough onto the baking sheet. These cookies will definitely expand so don’t make them too big. Bake for 10 – 13 minutes. My oven cooks super fast, but you want them to be turning golden brown when you take them out of the oven. Don’t let them get too brown, because they will cook while on the baking sheet.  After five minutes, remove from the cooking sheet and let the cool on a separate pan with parchment paper.

(4) When the cookies have cooled, combine the powdered sugar, milk, melted butter and vanilla extract in a small bowl. Whisk until smooth.

(5) Now you can take a spoon and spread some around the top like I did in this photo:

or if you want zigzags, my trick is to put some of the icing in a small ziplock bag. Then I cut a very small piece of one of the bottom corners of the bag. Don’t cut too big of a slit, because then the icing will come out too fast. Then squeeze the icing out in lines over the cookies. Here are the zigzag cookies:

(6) Enjoy!!

** Really make sure these cookies are completely cooled before storing them. Since they are so soft and chewy, if you stack them before they are ready they will stick together. They’ll still be tasty, but ugly.