Recipe: Drunken cherry chocolate hamantaschen

A (not too) tipsy treat that's perfect for Purim


Photo: Baila Gluck

  • place PRE 20 - 30 minutes plus chilling
  • place COOK 12 - 14 minutes
  • place SERVES Makes: 60 - 70 cookies
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"Hamantashen memories" from Naomi Ross, author of The Giving Table by Naomi Ross 

"As a kid in my mother’s house, I’d use a drinking glass to cut out my rounds of dough for hamantashen, the traditional triangular Jewish cookies made for the holiday of Purim. 

Dipping the rim in flour, it was a careful practice of cutting as close together as possible, leaving the least amount of scraps behind (the fewer scraps to re-roll, the better – the dough tends to get tougher with each redo).  

The tradition to give mishloach manot – festive food gifts – on Purim spurred my desire for fun after-school projects in the days leading up to the holiday. For a young person, taking ownership of preparing a package to give to others was a momentous experience. It required me to think about someone else and how to make it special for them. We kept it simple – traditional apricot or prune filled. No frills, but delicious all the same.

Now, as an adult with my own family, I have fun playing with different versions and more sophisticated flavors. Drunken cherry-Chocolate is a favorite that made it into my book. One year I used guava paste and lime.  Each year my family prepares and gives several packages to friends and neighbors, but lately, I also try to think of someone who in particular needs a lift or smile and make sure they get one too.  That extra attention and loving touch make a difference, especially when cooking for others. 

Those pesky, sealed edges of the hamantashen can re-open when baking… always pinch twice!"

In this recipe, despite the name, the alcohol cooks out…leaving a lusciously decadent filling.

Drunken Cherry-Chocolate Hamantaschen recipe:


  • Prepare dough: Cream the oil and sugar together in an electric mixer until a grainy paste forms. Beat in eggs, milk, and vanilla until well blended.

  • Mix: In a separate large bowl, sift together the flour, cocoa, baking powder, and salt. Slowly add the flour mixture to the batter, a little at a time, mixing at low speed until the dough comes away from the sides of the bowl and forms into a ball. Wrap in cling film and refrigerate for at least two hours or overnight. While dough chills, prepare the filling.

  • Filling: Combine all filling ingredients in a medium saucepan and stir to blend until all cornflour is dissolved and no lumps are visible.

  • Place saucepan over medium heat and bring to a simmer. Cook for 5–7 minutes, stirring often, until mixture is thickened and bubbly. Remove from heat to cool; chill to thicken.

  • Roll and fill: Preheat oven to 180°C. Line three baking sheets with parchment paper. Divide dough into four parts. Roll out the dough on a lightly floured board (it helps to flour rolling pin as well) into a very thin round — about 2 – 5mm thick. Using a 7cm – 9 cm diameter cookie cutter or glass, cut circles in the dough. Place one cherry with a little of the sauce in the centre of each circle. Shape into a triangle by folding the three sides inwards toward the centre (leaving space for the filling to be open and visible); pinch the sides together tightly.

  • Bake: Place hamantaschen 2cm apart on prepared baking sheets (pinch again to secure folds). Bake for 12–14 minutes. Be careful not to overbake. Repeat with remaining dough, using up dough scraps as well. Transfer baked hamantaschen to racks to cool.

Chef’s Touch: For a pretty look, drizzle with a little melted white chocolate (or dip one-half of the hamantasch into white chocolate).
Do Ahead: Dough can be prepared up to three days in advance. The filling can be made up to a week in advance.

Recipe adapted form The Giving Table by Naomi Ross with permission from Menucha Publishers.

First published in the JC February 2023



180 ml(3/4 cup)flavourlessoil

225g (1 cup) caster sugar

3 eggs

60ml (¼ cup) milk or soy/oat milk

1½ tsp pure vanilla extract

450g (3 ½ cups) flour, plus more for flouring

85g (2/3 cup) cocoa powder

4 tsp baking powder

¼ tsp salt

Drunken Cherry Filling

340g (12oz) frozen dark pitted cherries, thawed

80ml (1/3 cup) dry red wine

50g (¼ cup) sugar

1 tbsp cornflour

¼ tsp cinnamon

Special Equipment

Rolling pin

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