Chocolate Hamantaschen


When I first saw Martha Stewart’s recipe for chocolate hamantaschen in this month’s issue of Living magazine, I knew I had to make them. Though I wouldn’t pass up a traditional hamantaschen, which are typically eaten on Purim, they’re not at the top of my list of favorite desserts. Most of the hamantaschen I’ve had in the past are quite dense, a bit dry, and lacking in my favorite dessert ingredient – chocolate.


In honor of last week’s Purim holiday, I decided to test out these new and improved hamantaschen. Though I am not religious, I will always be in support of celebrating a holiday – religious or otherwise – when there is good food involved.


Martha’s recipe looked pretty close to perfection, but as I mentioned in my last blog post, I eat mostly gluten-free now, so I wanted to make these cookies with a gluten-free twist. I decided on using half gluten-free all-purpose flour and half almond flour since I’ve found that combining different gluten-free flours often yields the best result. (The all-purpose flour mix I used consisted of mostly rice flour.)


I also reduced the amount of sugar to make these cookies just a tad bit healthier. But I didn’t sacrifice on the butter. Despite the griping from my older brother, I decided not to experiment with substituting the butter for coconut oil. Maybe I’ll try this substitution another time, but I wanted a guaranteed good result with this first batch.


The results did not disappoint. These hamantaschen are quite the improvement from the hamantaschen I ate as a kid in Hebrew school. The dough bakes up moist and buttery, the orange zest works its magic to delicately balance the richness of the chocolate, and the chocolate center is the perfect filling.


My mom said she would eat these cookies plain without the signature hamantaschen center, as the dough was delicious as is. My brother suggested using Nutella for the filling — an indulgent suggestion I just might take next time.

Whether you celebrate Purim or not, these cookies are worth the multi-step process. I’m typically a fan of easy, one-bowl cookies that go straight into the oven, but the chilling in this recipe is essential in order to roll out the dough. You will not think this extra time wasted once you taste these cookies.

Give these hamantaschen a try, experiment with the different flours and fillings, and let me know how they turn out. Happy Purim, but mostly happy baking!






Chocolate Hamantaschen

Makes about 36 medium-sized cookies

Adapted from Martha Stewart

–       2 sticks unsalted butter

–       1 ¼ cups sugar in the raw

–       2 tsp. vanilla extract

–       zest of one orange

–       2 eggs, plus 1 egg for an egg wash before baking

–       2 cups all-purpose gluten-free flour, plus more for rolling out the dough

–       2 cups finely ground almond flour (I used this brand which my mom and I happily spotted at Costco.)

–       1 tsp. salt, plus more for sprinkling before baking

–       1 ½ tsp. baking powder

–       3 oz. semisweet chocolate, finely chopped

–       7 oz. semisweet chocolate chips or chunks

Beat butter and sugar together until fluffy and pale in color, about 3-4 minutes. Add vanilla extract, orange zest, and 2 eggs. Add flours, salt, and baking powder, beating until incorporated. Add finely chopped chocolate, and mix until combined. Form dough into three disks, and wrap each in plastic wrap. Refrigerate for about one hour.

Roll out dough, one disk at a time, on a floured surface. Dough should be about a 1/4 inch thick. Cut out circles using a cookie cutter or a round drinking glass, and place on cookie sheet. Whisk the remaining egg with a little water, and brush egg wash around the edges of the circular cookies. Place chocolate chips or chunks in the center of each cookie. Form the cookies into triangles, and freeze for about 30 minutes. Sprinkle each cookie with a little salt to make the chocolate flavor pop. Bake cookies at 350 degrees F for about 20-25 minutes, or until the dough turns golden brown.


6 thoughts on “Chocolate Hamantaschen

  1. My Dear Niece Nicole,
    Your food blog is all well and good, but tell me how do you propose we viewers keep from licking the screen? Y-u-u-u-m!!

    Your CA aunt

  2. Dear Nicole
    This is my my first time commenting on anyone’s blog! Being a foodie myself I thoroughly enjoyed your interpretation on both recipes. Yummy! Having just got back from Israel, I can tell you for sure that there was not a hamantaschen that tasted nearly as good as your recipe looks!!
    Looking forward to your next blog…
    Aunt Val

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