No it’s not alcoholic.
Yes, the alcohol cooks out . . . leaving a lusciously decadent filling.
Yes, cherries and chocolate belong together.
And yes, give some to your friends . . . if there are any left.
Yields: 5–6 dozen
Prep Time: 20–30 minutes plus chilling time
Cook Time: 12–14 minutes
Difficulty: Worth the Wait
Freezer Friendly
Chef’s Note: DO AHEAD—Dough can be prepared up to 3 days in advance. Filling can be made up to a week in advance.
For Dough:
• 3⁄4 cup oil
• 1 cup sugar
• 3 eggs
• ¼ cup milk or soymilk/oatmilk
• 1½ teaspoons pure vanilla extract
• 3½ cups flour (plus more for flouring board/pin)
• 2⁄3 cup Dutch process cocoa
• 4 teaspoons baking powder
• ¼ teaspoon salt
For Drunken Cherry Filling:
• 1 (12-ounce) bag frozen dark pitted cherries, thawed
• 1⁄3 cup dry red wine
• 1⁄4 cup sugar
• 1 tablespoon cornstarch
• 1⁄4 teaspoon cinnamon
Directions:
1. For 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.
2. 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 plastic wrap and refrigerate for at least two hours or overnight. While dough chills, prepare the filling:
3. For Filling: Combine all filling ingredients in a medium saucepan and stir to blend until all cornstarch is dissolved and no lumps are visible.
4. 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.
5. Roll & Fill: Preheat oven to 350° Line 3 baking sheets with parchment paper. Divide dough into 4 parts. Roll out the dough on a lightly floured board (it helps to flour your rolling pin as well) into a very thin round—about 1⁄8–1⁄4 inch thick. Using a 3–3½” diameter cookie cutter or glass, cut circles in the dough. Place 1 cherry with a little of the sauce in the center of each circle. Shape into a triangle by folding the 3 sides inwards toward the center (leaving space for the filling to be open and visible); pinch the sides together tightly.
6. Bake: Place hamantaschen 1 inch apart on prepared baking sheets (pinch again to secure folds). Bake for 12–14 minutes. Be careful not to overcook. Repeat with remaining dough, using up dough scraps as well. Transfer baked hamantashen to racks to cool.
Chef’s Touch: For a pretty look, drizzle with a little melted white chocolate (or dip one half of the hamantash into white chocolate).
Naomi Ross is a cooking instructor and food writer based in Woodmere, New York. She teaches classes throughout the country and writes articles connecting delicious cooking and Jewish inspiration. She is the author of The Giving Table (Brooklyn, NY, 2022).