Filled Raisin Cookies

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Filled Raisin Cookies – A Generational Recipe Passed Down with Love—Mini Pies of Nostalgia and Comfort

Introduction

These Filled Raisin Cookies are more than just a holiday treat—they’re a labor of love, a tribute to generations past, and the one thing your dad looks forward to every Christmas. With a tender, lightly sweetened dough and a rich filling of simmered raisins, orange zest, and pecans, each cookie is like a mini pie wrapped in memory.

The recipe has been passed down through your family, likely from your grandmother’s grandmother, and refined through trial and error. It’s the kind of bake that takes time, care, and intention—but the reward is a cookie that’s deeply satisfying and steeped in tradition.

Ingredients

For the Dough

  • 2 cups granulated sugar
  • 1 cup Crisco shortening
  • 4 large eggs
  • 2 tsp salt
  • 1 tbsp vanilla extract
  • 1 cup milk
  • 3 heaping tsp baking powder
  • ~7 cups all-purpose flour (start with 6 and add more as needed for rolling consistency)

For the Raisin Filling

  • 3 boxes raisins (12 oz each; you may have some leftover)
  • ½ cup granulated sugar
  • 3 tbsp cornstarch
  • Zest of 1 medium orange
  • 1½ cups chopped pecans
  • Enough water to cover raisins

Instructions

Step 1: Make the Filling

  1. In a saucepan, combine raisins, sugar, orange zest, and enough water to just cover the raisins.
  2. Bring to a healthy simmer, stirring often.
  3. In a separate bowl, whisk cornstarch with a bit of water until smooth.
  4. Slowly pour into the raisin mixture and simmer until thickened.
  5. Stir in chopped pecans.
  6. Remove from heat and let cool completely.

Step 2: Make the Dough

  1. Preheat oven to 375°F (190°C). Line baking sheets with parchment paper.
  2. In a large bowl, cream together sugar and shortening until fluffy.
  3. Add eggs, salt, vanilla, and milk; mix well.
  4. Sift baking powder into 6 cups of flour. Gradually add to wet mixture.
  5. Continue adding flour until dough is soft but rollable—not sticky, not dry.

Step 3: Assemble the Cookies

  1. Roll dough on a well-floured surface to ⅛–¼ inch thickness.
  2. Cut into 3-inch circles.
  3. Place a rounded teaspoon of cooled filling onto half the circles.
  4. Top with another circle and seal edges—use water on your fingertip to help seal, or a crimping tool like a “cut-n-seal.”
  5. Transfer to baking sheet.

Step 4: Bake

  1. Bake for 18–20 minutes, or until lightly golden.
  2. Cool on pan for 5 minutes, then transfer to wire rack.
  3. Store in airtight containers. Freeze in batches to enjoy year-round.

Tips for Success

  • Use parchment paper to catch any filling that bubbles out.
  • Don’t skip the cooling step for the filling—it helps the cookies seal better.
  • Chill dough briefly if it becomes too soft while rolling.
  • Use a cookie scoop for consistent filling portions.
  • Freeze in layers with parchment between cookies to prevent sticking.

Serving Suggestions

  • Serve with hot tea, coffee, or spiced cider.
  • Add to holiday cookie trays with shortbread and gingerbread.
  • Enjoy warm with a scoop of vanilla ice cream.
  • Gift in tins with handwritten notes about the recipe’s history.

Variations to Try

  • Nut-Free Version: Omit pecans or use sunflower seeds.
  • Spiced Filling: Add cinnamon, nutmeg, or clove to the raisin mixture.
  • Citrus Twist: Use lemon zest instead of orange.
  • Jam-Filled: Try fig, apricot, or cherry preserves for a fruity variation.
  • Mini Pie Style: Use a fork to crimp edges and brush tops with milk or egg wash.

Storage & Freezing

  • Store in airtight containers for up to 5 days.
  • Freeze in batches for up to 3 months.
  • Thaw at room temperature or warm gently in the oven.

Behind the Recipe

This recipe is a testament to love passed down through generations. From your grandmother’s handwritten notes to your dad’s yearly request, these cookies are more than ingredients—they’re tradition, memory, and care baked into every bite. The time it takes to make them is part of the gift, and the joy they bring lasts long after the last crumb is gone.

Conclusion

These Filled Raisin Cookies are tender, sweet, and filled with history. Whether you’re baking them for Christmas, a family reunion, or just to keep tradition alive, they’re a labor of love worth every minute.

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