← Back to Blog

Pumpkin Cookie Pops — The Annual Cookie Tradition That Keeps Us Warm

December. Christmas season. The apartment is decorated — tree, lights, the "Mr. & Mrs. Kowalski" ornament from last year now joined by a new ornament Megan bought: a miniature pierogi in silver. She hung it on the tree and said, "Our family crest." She's not wrong. If the Kowalskis had a coat of arms, it would be a pierogi on a field of sauerkraut with the motto "Don't Be Fancy."

The brewery is in holiday mode. Gift packs, winter beers, the taproom decorated with lights and garland. The cherry sour launched — the collaboration with the Door County cidery — and it's the most popular sour we've ever made. Tart, cherry-forward, with a rosé-like color that photographs beautifully. Social media went wild. The head brewer said, "You made a pretty beer." From him, this is both a compliment and a slight criticism. He thinks beer should be rustic. I think beer should be whatever makes people happy. We agree to disagree. We always agree to disagree.

Nine months of trying. December is hard for waiting. Everyone asks about kids at Christmas. "Any news?" "When are you going to make us grandparents?" Linda asks gently, with love. Colleen asks boldly, with wine. We smile and say "we're working on it" and change the subject and go home and hold each other and hope. The hope is getting tired. Not gone. Just tired. Hope is a muscle and nine months of flexing it makes it sore.

Made gingerbread cookies. The annual tradition. Megan iced them with precision. Mine look like they were decorated during an earthquake. We ate them on the couch and watched Christmas movies and the tree glowed and the pierogi ornament caught the light and everything was warm and waiting and beautiful.

The gingerbread is our annual ritual — Megan’s precise icing versus my earthquake-level decorating — but some years I want to bring something a little different to the couch, something that feels festive and forgiving and fun to decorate badly. Pumpkin cookie pops have that same warm-spice energy as gingerbread but with a softness that feels right when the hope in your chest is tired and you just need something sweet in your hand and the tree glowing in front of you. These are the cookies you make when you want the tradition without the pressure.

Pumpkin Cookie Pops

Prep Time: 20 min | Cook Time: 14 min | Total Time: 34 min (plus cooling) | Servings: 24 cookie pops

Ingredients

  • 2 1/4 cups all-purpose flour
  • 1 tsp baking soda
  • 1 1/2 tsp ground cinnamon
  • 1/2 tsp ground nutmeg
  • 1/4 tsp ground cloves
  • 1/4 tsp ground ginger
  • 1/2 tsp salt
  • 1/2 cup (1 stick) unsalted butter, softened
  • 3/4 cup granulated sugar
  • 1/4 cup packed brown sugar
  • 1 large egg
  • 1 cup canned pumpkin puree (not pie filling)
  • 1 tsp pure vanilla extract
  • 24 lollipop or cookie sticks
  • For the icing: 1 1/2 cups powdered sugar, 2–3 tbsp milk, gel food coloring (optional)

Instructions

  1. Preheat and prep. Preheat oven to 350°F. Line two baking sheets with parchment paper and set aside.
  2. Mix dry ingredients. In a medium bowl, whisk together flour, baking soda, cinnamon, nutmeg, cloves, ginger, and salt. Set aside.
  3. Cream butter and sugars. In a large bowl, beat softened butter with both sugars on medium speed until light and fluffy, about 2–3 minutes.
  4. Add wet ingredients. Beat in the egg, pumpkin puree, and vanilla until fully combined. The mixture will look slightly curdled — that’s normal.
  5. Combine. Add the dry ingredients to the wet and stir until just combined. Do not overmix. Dough will be soft and sticky.
  6. Scoop and stick. Drop rounded tablespoons of dough onto prepared baking sheets, spacing about 2 inches apart. Gently press a lollipop stick about halfway into the base of each dough mound and smooth the dough back around the stick to secure it.
  7. Bake. Bake for 12–14 minutes until the edges are set and the tops are no longer glossy. Centers will look soft — they firm up as they cool. Do not overbake.
  8. Cool completely. Let cookies rest on the baking sheet for 5 minutes, then transfer carefully (holding by the stick) to a wire rack. Cool completely before icing.
  9. Make the icing. Whisk powdered sugar with milk one tablespoon at a time until you reach a thick but pipeable consistency. Divide into small bowls and tint with gel food coloring if desired.
  10. Decorate. Ice the cooled cookie pops however feels right. Precision optional. Earthquake style welcome.

Nutrition (per serving)

Calories: 145 | Protein: 2g | Fat: 4g | Carbs: 26g | Fiber: 1g | Sodium: 110mg

Jake Kowalski
About the cook who shared this
Jake Kowalski
Week 446 of Jake’s 30-year story · Milwaukee, Wisconsin
Jake is a twenty-nine-year-old brewery worker, newlywed, and proud Polish-American from Milwaukee's Bay View neighborhood. He didn't start cooking until his grandmother Babcia Helen passed away and left behind a stack of grease-stained recipe cards. Now he makes pierogi from scratch, smokes meats on a balcony smoker his landlord pretends not to notice, and writes for guys who want to cook good food but don't know a roux from a rub.

How Would You Spin It?

Put your own twist on this recipe — what would you add, remove, or swap?