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Gingerbread Hamantashen with Spiced Apple Filling

Gingerbread Hamantaschen with Spiced Apple Filling

I love ginger in all its forms, pickled for sushi, candied and especially ground inside little gingerbread people. When I first tried baking Gingerbread Men quite a few years back, after trying my first gingerbread latte, I felt like I was doing something wrong. Gingerbread Men have long been associated with the secular holiday season, but there’s nothing remotely religious about them except for the heavenly taste and no reason why we can't make and enjoy ginger cookies in any form. 

I couldn't be any happier with the way these came out! Even my not so ginger happy husband gave me a big thumbs up when I twisted his arm into trying one hot and fresh from the oven, I mean really who could resist? Whatever you have planned for your mishloach manot, these Gingerbread Hamantashen should be added to your list. For our michloach manot, we’re going to put them in large mugs with our own special blend of looseleaf Chai Tea and Spiced Chocolate Truffles. Who is going to want winter to end now?

  • Duration
  • Cook Time
  • Prep Time
  • 36 cookiesServings


For the cookie dough:

  • 2 cups whole wheat flour
  • 1 cup all purpose flour plus more fore dusting
  • 1 teaspoon baking soda
  • ¾ teaspoon ground cinnamon
  • 1½ teaspoon ground ginger
  • ½ teaspoon ground allspice
  • ½ teaspoon ground cloves
  • ½ teaspoon salt
  • ¼ teaspoon freshly milled black pepper
  • 8 tablespoons (1 stick) vegan butter, room temperature
  • ¼ cup vegetable shortening or coconut oil, at room temperature
  • ½ cup packed light brown sugar
  • ⅔ cup unsulfured molasses
  • 1 large egg

For the filling:

  • 6 tablespoons vegan butter, cut in 1-inch pieces
  • ½ vanilla bean, cut lengthwise and scraped of seeds
  • 3 large or 4 medium apples, peeled, cored and cut into eighths
  • ¼ cup brown sugar, packed


Prepare 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 butter 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.)

Prepare Filling:

1. In a large skillet over medium heat add the butter 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.

When ready to assemble and bake the cookies -

1. Position the racks in the top and bottom thirds of the oven and preheat to 350℉.

2. 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.

3. Spoon a teaspoon of filling into the center of the circle of dough and fold together to form a triangle.

4. Bake for 8-10 minutes, remove to wire rack to cool and enjoy.