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Stuffed Cherry Pie Cookies -- The Glaze That Started Everything

Back to the grind. Summer production at the brewery is relentless — we're brewing four days a week, double what we do in winter. The summer wheat is moving fast, the light lager is outselling everything, and I'm running lead brew days twice a week now. Two lead days. That's head brewer workload. I'm twenty years old. Marcus said something this week that stuck: "You're outgrowing me." I laughed because that's absurd — Marcus has twenty years on me. But he clarified: "I mean you're developing a style I can't teach you. The Polish thing, the personal recipes — that's yours. I gave you the tools. You built the house." I didn't know what to say to that. Marcus is the best teacher I've ever had, including every actual teacher I had in school. Hearing him say I've gone beyond what he can offer is... I don't know. Flattering and sad and exciting all at once. At home, I've been cooking with more confidence. Wednesday I made a pork tenderloin with a cherry glaze — inspired by the Door County cherry wheat we brewed last year. Seared the tenderloin, then baked it with a sauce of cherries, brown sugar, balsamic vinegar, and a splash of beer. The pork was pink in the middle (thermometer: 145, don't worry Mom), and the cherry glaze was sweet and tangy and the kind of thing that makes you close your eyes when you taste it. Posted it on Instagram. A follower commented: "You should write a food blog." A blog. Me. The guy who spelled "restaurant" wrong until he was eighteen. But the idea nagged at me all week. Writing about food. Not just photos — stories. The kind of stories I tell Kevin at the bar. The kind of stories Babcia tells with her hands in the dough. Maybe someday. Sunday at Babcia's: she made a summer fish dish — baked trout with lemon and dill. Light, clean, seasonal. She ate less than usual. Mom noticed. I noticed. We said nothing. The Kowalski approach to concern: observe, worry silently, bring soup.

The cherry glaze on that pork tenderloin—the one Marcus never even got to taste—was the thing that made me think maybe I actually have a palate worth trusting. Sweet, tangy, a little dark from the balsamic: it tasted like something I invented, not something I followed. When I wanted to chase that same feeling in a dessert, these stuffed cherry pie cookies made all the sense in the world. Same fruit, same balance of tart and sweet, same impulse to close your eyes when you bite in. Babcia would approve—she’s always said the best recipes are the ones you can trace back to a feeling.

Stuffed Cherry Pie Cookies

Prep Time: 20 min | Cook Time: 14 min | Total Time: 34 min | Servings: 24 cookies

Ingredients

  • 2 1/4 cups all-purpose flour
  • 1/2 tsp baking soda
  • 1/2 tsp salt
  • 1 cup (2 sticks) unsalted butter, softened
  • 3/4 cup granulated sugar
  • 3/4 cup packed light brown sugar
  • 2 large eggs
  • 1 tsp pure vanilla extract
  • 1 cup cherry pie filling (about 24 individual cherries with a little sauce)
  • 1/2 cup white chocolate chips (optional, for drizzle)
  • 1 tbsp powdered sugar, for dusting

Instructions

  1. Preheat oven. Heat oven to 375°F. Line two baking sheets with parchment paper and set aside.
  2. Mix dry ingredients. Whisk together flour, baking soda, and salt in a medium bowl. 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 3 minutes. Add eggs one at a time, beating after each addition. Mix in vanilla.
  4. Combine. Gradually add the flour mixture to the butter mixture, stirring until just combined. Do not overmix — stop as soon as no dry streaks remain.
  5. Portion the dough. Scoop about 1 1/2 tablespoons of dough and flatten it into a small disc in your palm. Place 1 whole cherry (with just a small bit of the sauce) in the center.
  6. Seal and shape. Fold the dough up and around the cherry, pinching the seam closed firmly. Roll gently into a ball and place on the prepared baking sheet 2 inches apart. Repeat with remaining dough and cherries.
  7. Bake. Bake 12–14 minutes, until the edges are just golden and the centers look barely set. Do not overbake — they firm up as they cool.
  8. Cool. Let cookies rest on the baking sheet for 5 minutes before transferring to a wire rack to cool completely.
  9. Finish (optional). Melt white chocolate chips in a small bowl in 30-second microwave intervals, stirring between each. Drizzle over cooled cookies and dust lightly with powdered sugar before serving.

Nutrition (per serving)

Calories: 198 | Protein: 2g | Fat: 9g | Carbs: 28g | Fiber: 1g | Sodium: 112mg

Jake Kowalski
About the cook who shared this
Jake Kowalski
Week 67 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.

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