Gingerbread Hamantaschen with Spiced Apple Filling

Prep Time: 30 minutes; Cook Time: 10 minutes; Servings: 36. 


For the cookie dough:

  • 2 cups whole wheat flour
  • 1 cup all purpose flour plus more fore dusting
  • 1 teaspoon baking soda
  • 1/4 cup brown sugar, packed
  • 3/4 teaspoon ground cinnamon
  • 1 1/2 teaspoon ground ginger
  • 1/2 teaspoon ground allspice
  • 1/2 teaspoon ground cloves
  • 1/2 teaspoon salt
  • 1/4 teaspoon freshly milled black pepper
  • 8 tablespoons (1 stick) unsalted margarine, room temperature
  • 1/4 cup vegetable shortening, at room temperature
  • 1/2 cup packed light brown sugar
  • 2/3 cup unsulfured molasses
  • 1 large egg

For the filling: 


  • 6 tablespoons margarine, cut in 1-inch pieces
  • 1/2 vanilla bean, cut lengthwise and scraped of seeds
  • 3 large or 4 medium apples, peeled, cored and cut into eighths
  • 1/4 cup brown sugar, packed


Gingerbread cookie dough: 

1. Sift the flours, baking soda, cinnamon, ginger, allspice, cloves, salt and pepper through a wire sieve into a medium bowl. Set aside. 

2. In a stand mixer, beat the margarine and shortening on high until well blended, about 1 minute. Add the brown sugar and beat until the mixture is light in texture and color, about 2 minutes. Beat in the molasses and egg. Using a wooden spoon, gradually mix in the flour mixture to make a stiff dough. Divide the dough into two thick disks and wrap each disk in plastic wrap. Refrigerate until chilled, about 3 hours. (The dough can be prepared up to 2 days ahead.)


1. In a large skillet over medium heat add the margarine and vanilla bean and seeds, cook about 5 minutes. Add the apples and let them caramelize on one side, then turn and cook until it beings to caramelize. Sprinkle the brown sugar over the apples and cook turning occasionally while it softens about 10 minutes. Remove from heat and remove vanilla bean, then puree in food processor and cool until ready to use.

2. When ready to assemble and bake the cookies, position the racks in the top and bottom thirds of the oven and preheat to 350° F.

3. To roll out the cookies, work with one disk at a time, keeping the other disk refrigerated. Remove the dough from the refrigerator and let stand at room temperature until just warm enough to roll out without cracking, about 10 minutes. (If the dough has been chilled for longer than 3 hours, it may need a few more minutes.) Place the dough on a lightly floured work surface and sprinkle the top of the dough with flour. Roll out the dough 1/8 inch thick. Cut out 3-inch circles and use a spatula to place circles on a baking sheet lined with parchment.

4. Spoon a teaspoon of filling into the center of the circle of dough and fold together to form a triangle. Bake for 8-10 minutes, remove to wire rack to cool, and enjoy.