A Blustery Day Calls for This Winnie the Pooh Pie

image source: jessica lucius | disney family

Oh, bother! The holidays are almost here, but this cranberry apple pie is just the thing to share with friends or warm up with on a blustery day.

I always look forward to holiday baking because it’s the perfect chance to make something extra special for family and friends. In my family, Thanksgiving means lots of food, laughter, and pie!  This year, I thought it would be fun to put a fall spin on the classic apple pie with the addition of tart cranberries. Nothing warms up a blustery day quite like a slice of freshly baked pie AND the adorable Winnie the Pooh. So, I added one of my favorite Disney characters to the mix.

Premade pie dough makes this recipe truly easy as pie, and with the help of cookie stamps and a little colored dough (plus, those glittery sugared cranberries), you’ll have an impressive and delicious treat when it’s time for something sweet.

For more magical DIYs, try this Winnie the Pooh Fall Wreath:

Winnie the Pooh Pie


  • PIE:
  • 2 sheets store-bought pie dough
  • 9″ pie pan
  • Winnie the Pooh template
  • Heavy cardstock
  • Leaf-shaped cookie stamps
  • Red and green gel food coloring
  • 8 cups tart apples (peeled, cored, and sliced 1/4″ thick)
  • 1 3/4 cups fresh or frozen cranberries
  • 1 tablespoon lemon juice
  • 2 tablespoons cornstarch
  • 1 cup sugar, plus more for sprinkling
  • 1 teaspoon ground cinnamon
  • 1/2 teaspoon apple pie spice
  • 1/2 teaspoon grated orange peel
  • 2 tablespoons butter, cold
  • 1 egg, beaten
  • 1/2 cup fresh cranberries
  • 1/4 cup water
  • 1/4 cup sugar, plus 3 tablespoons more for coating cranberries
  • 1/8 cup chocolate chips

Helpful Tip

All cutting should be done by an adult.


  1. On a lightly floured surface, roll one piece of pie dough out into a 12-inch circle.

  2. Carefully transfer the dough to an ungreased pie pan, and crimp the edges (using your fingers or fork). Transfer to the refrigerator.

  3. You can use the Winnie the Pooh template as a guide to cut your shapes out of cardstock (you do not want any marker or ink on your cardstock as it will be touching the pie dough).

  4. Roll the second piece of pie dough out into a 12-inch circle, and use a sharp knife to cut around your Winnie the Pooh shape. Then use your leaf cookie stamps to cut as many leaves out as you want.

    image source: jessica lucius

  5. Transfer all cut out shapes to a baking sheet lined with parchment paper.

  6. Gather the scrap dough, and use gel food coloring to color one half red and the other green. Roll each color out, and again using your cardstock as a guide, cut the shirt out of red, and the scarf out of the green dough. Place these shapes on your baking sheet and transfer the sheet to the freezer for 15 minutes.

  7. Preheat the oven to 400° F.

  8. In a large mixing bowl, combine the apples, cranberries, lemon juice, cornstarch, sugar, cinnamon, apple pie spice, and citrus peel. Transfer the pie filling to your refrigerated pie shell. Cut the cold butter into small pieces and place around the top of the pie.

    image source: jessica lucius

  9. Arrange the leaf cutouts in any pattern you desire around the edges, keeping an open spot in the middle of the pie for Winnie the Pooh. Use a little water if needed to get any leaves to stick, and to add the shirt and scarf to your Winnie the Pooh cutout. Place Winnie the Pooh back in the freezer while the pie bakes.

    image source: jessica lucius

  10. Lightly brush the leaf cutouts with egg wash and sprinkle with a little sugar.

  11. Place the pie pan on a baking sheet, and bake for 20 minutes. Then, with the pie in the oven, lower the temperature to 350° F and bake for another 30-40 minutes. If the edges of the crust are getting too brown you can add foil (just fold a 12” piece into a square, cut a circle out, and carefully place over the edges of the pie).

  12. While the pie is baking, you can make sugared cranberries to add for decoration. Place 1/4 cup of water and 1/4 cup of sugar in a small saucepan and cook over medium heat, stirring occasionally, until sugar dissolves and it comes to a simmer. Remove from the heat. Carefully add in your cranberries, cover, and let steep for 5 minutes. Then transfer to a piece of parchment paper to cool for about 1 hour before rolling in the extra 3 tablespoons of sugar.

  13. When the pie is done baking, transfer to a cooling rack to set for at least 1 hour before slicing. Then place your Winnie the Pooh dough in the oven for 10 minutes (after adding a little egg wash and sugar to it as well).

  14. Remove the cutouts and allow to cool on a wire rack for about 15 minutes before using a toothpick and melted chocolate to add the face. You can either melt the chocolate over a double broiler, or in the microwave in 30-second intervals at 50% power (stirring in between each interval).

  15. Once everything is set, place Winnie the Pooh in the middle of your pie, decorate with sugared cranberries, and enjoy!

Posted 3 years Ago
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