Chocolate Raspberry Hamentashen

These delicious, crisp chocolate cookies are gluten and dairy free. Filled with homemade chia-raspberry jam, they're a decadent, but low-sugar, pick me up any time of day.

I've mentioned before how my parents, particularly my mom, grew up in a neighbourhood full of Jewish families and as such became good friends with many of the kids. As I was growing up, not only did I accompany my folks to Hanukkah parties almost every year, but I was able to learn about many Jewish holidays and customs at my school and through my friends as well. Obviously, Hanukkah was always the "favourite" celebration of the winter - even more so than Christmas, since at school we were allowed to play with dreidels (complete with chocolate gelt) and eat latkes in class as a "cultural" lesson. Other holidays such as Rosh Hashana, Yom Kippur, Purim and Passover, on the other hand, were mentioned but never really elaborated on. It was only when I started taking world religion classes in highschool that I began to recognize their differences and appreciate what my friends were observing.

While not a traditional Passover treat, hamentashen (or if you prefer, hamantaschen) have a cultural symbolism that is significant for both this holiday and Purim, when it's commonly served.Both holidays celebrate the triumph of the Jewish people over evil - with Purim, it's in the form of Haman, who was planning to kill all the Jews in the Achaemenid Persian Empire, and it is from him that the shape and name of these cookies comes from. With Passover, it is the Egyptian Pharaoh who was defeated by the plagues, and subsequently freed the Jewish nation from slavery, and while that holiday has it's own set of culinary traditions and practices, I thought these cookies would be appropriate as well.

The whole reason I even decided to make this recipe (mostly "winging it" off one I found on Tori Avey) was because I was searching for a dairy free, gluten free cookie to bring to one of my acquaintances, who's son must avoid both foods. The original recipe wasn't gluten free, but looked fairly simple to swap in a mix of flour for - especially since I was only making a half recipe. In place of the starch I usually add to my gluten free flour mixes, I used cocoa powder. Along with the delicate nuttiness of the teff and the shot of coffee I used to help form the dough, the flavour was outstanding - no butter needed! To fill the little triangles I whipped up a raspberry jam with thawed frozen berries, a few tablespoons of chia seed and a tablespoon or so of honey. The leftover jam became the next morning's Toast Topper!

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Chocolate Raspberry Hamentashen
Adapted from Tori Avey
Makes ~18

1 egg
1/3 cup sugar
2 tbsp canola oil
2 tsp vanilla (alcohol free or paste for Passover)
½ cup brown rice flour
½ cup teff flour
2 tbsp cocoa
½ tsp guar gum
½ tsp baking powder
pinch salt
2 tbsp cold coffee
6 tbsp all-fruit, lower sugar raspberry jam (I used a homemade chia seed, honey and raspberry jam)

1. In a mixing bowl, whisk together the egg, sugar, oil, coffee and vanilla.
2. Add the flours, cocoa, guar gum, baking powder and salt, and mix to form a slightly crumbly dough.
3. By hand, knead until smooth. If too dry, add water slowly, 1 teaspoon at a time, using your hands to knead the liquid into the dough.
4. Wrap in plastic and chill 1 hour.
5. Heat oven to 350 F.
6. Roll the dough out to ⅛” thick and use a 3” cookie cutter or glass rim to cut circles out of the dough. Reroll dough as needed.
7. Place cut out shapes on a lined baking sheet and place a scant teaspoon of jam into the center of each circle.
8. Fold or pinch the hamentashen into their triangle shapes (I like this tutorial).
9. Bake at 350 degrees F for 18-20 minutes. Do not overbake.

*Be sure to use certified “Kosher for Passover” products if need be (all Bob’s Red Mill products are Kosher but not necessarily for Passover). 

Amount Per Serving
Calories: 65.9
Total Fat: 2.1 g
Cholesterol: 10.3 mg
Sodium: 5.2 mg
Total Carbs: 12.1 g
Dietary Fiber: 0.9 g
Protein: 1.3 g