I am pretty much a purist when it comes to Hamantaschen, which are definitely near the top of my list of favorite Jewish holiday treats. The flavor I crave is very specific- Poppyseed filling (mohn) with a buttery-lemony flavored dough that is both crisp and tender. However, I am seeing a whole bunch of fancy, non-traditional flavors popping up all over lately. I started dreaming up ideas, only to discover that they had been done already. Apple pie…done. Cheese Danish….done. The following Chocolate-covered Cherry Hamantaschen was my brain child, and after a pretty thorough search, I don’t think they exist yet: ) Here’s to trying something new!
For those of you new to the world of Hamantaschen, they are triangular shaped cookies traditionally eaten on Purim. Purim is a fun holiday where Jews dress up in costume and retell the story of Mordechai, Haman, Queen Esther, and King Ahashueros (Ahashveros). There are good guys, bad guys, a bit of drinking, near death for all, and a happy ending. It is a great time. Please look up the holiday for better details, as I didn’t mean to get into that here… However, the cookies are meant to represent Haman’s (the bad guy’s) hat or more literally and disturbingly…his ears. Hmmm, yum? But they are good, really!
First cream the butter, sugar, vanilla, salt, and baking powder together in your mixer. A hand mixer will work fine, as well. Add in your egg, and beat until well combined.
Then add your flour and cocoa powder. Mix until a thick dough forms. Do not over mix.
Form dough into a disk and cover in plastic. Stash in the fridge for 15 minutes.
In the meantime, line your pans with parchment. I love these new “cookie sheets” by Reynold’s. So easy!
Get your fillings en place. Although I am making chocolate covered cherry flavor, I can’t just leave it at one, so I have other accoutrements at the ready.
I dust the counters lightly with powdered sugar when making any type of roll out sugar cookie. I find that it makes re-rolls work out better, and doesn’t add a heavy over-floured feel.
Roll out dough to 1/8 inch.
Cut out circles or fluted circles, approximately 2 1/2″, but can be made smaller or larger as desired.
Line up circles on parchment.
Fill each circle with 3 cherries, no more, no less. A couple of years ago, I learned that there is an actual proper way to fold Hamantaschen, which involves folding each edge over the edge next to it, instead of pinching together. Check it out at the bottom of Tori Avey’s genius post here.
Here is a triple chocolate version I am making for my daughter who is not a fan of cherries…or cooked fruit in general. But that is a story for another day.
After filling and folding all the cuties, bake at 350 degrees for 12-14 minutes. You can see how well most of my cookies stayed together, but I did have one renegade. There is always one….
This is what you are going for!
Let cool completely. Melt chocolate chips in microwave in 30 second intervals, stirring in between. Drizzle, dunk, or dollop cookies with chocolate. I tried all three methods, and I settled on dollops.
Here is a finished cookie. I feel that it would be lovely with chopped walnuts sprinkled on top, but we are nut-free, so that is a no-go.
My hot chocolate version was adorable, if I do say so, though! They are filled with mini-mallow bits (the kind in a canister that don’t puff when heated), then topped with more chocolate and marshmallows. You could totally fill these with anything you want- Peanut Butter, caramel, jams, white chocolate, etc….
Chocolate Covered Cherry Hamantaschen
For the dough:
- 1/2 cup (1 stick) unsalted butter, room temperature (or margarine, if pareve is desired)
- 3/4 cup sugar
- 1 teaspoon vanilla extract
- 1/2 teaspoon salt
- 1/2 teaspoon baking powder
- 1 egg
- 1 3/4 cup flour
- 1/2 cup unsweetened dark cocoa powder
- Powdered sugar for dusting
For filling and topping:
- 1 can cherry pie filling (or make your own, like I did)
- 3/4 cup semi-sweet chocolate chips
- 1/4 cup chopped walnuts (optional)
Preheat oven to 350 degrees. Line two baking sheets with parchment paper.
In the bowl of a stand mixer, cream butter, sugar, vanilla, salt, and baking powder until fluffy. Add in egg, mixing well to combine. Mix flour and cocoa powder, and add to mixer. Starting on lowest speed, mix just until stiff dough comes together. Wrap in plastic and refrigerate for 15 minutes or up to 1 day. Let dough come back to room temperature before rolling.
Sprinkle work surface with powdered sugar. Roll out dough to 1/8 inch. Using round cookie cutters, cut out as many rounds as possible. Can re-roll scraps once, if necessary. Place rounds onto parchment.
Place three cherries in the center of each round. Fold dough into a triangle around the filling, pinching points together gently. If dough is a tad crumbly (from being cold or too much powdered sugar), just pinch together and it will still work when baked. Bake for 12-15 minutes (mine took 14). Cookies will still be slightly soft when hot, but will firm up as they cool. Cool completely.
Melt chocolate in microwave safe bowl by 30 second intervals, stirring in between. Dollop approximately 1 teaspoon melted chocolate over top of filling triangle in center. Sprinkle with nuts, if desired. Let chocolate set up at room temperature or in fridge, and serve.
* for hot cocoa variation, stuff each cookie circle with chocolate chips and mallow bits. Do not use mini-marshmallows, as they will puff when baked! Bake and top with melted chocolate and more mallow bits. Enjoy!