Raspberry Chocolate Hamentaschen

by rivka on February 19, 2013 · 14 comments

in cookies and bars, events

The Jewish holiday of Purim was my favorite as a kid. It was the one day of the year when I got to skip the skirt in favor of sweat pants at school (clue: put on a whistle and, oh look, you’re a coach). We got dismissed early, had a carnival for most of the day, and ate ourselves silly. Most of that eating was hamentaschen, which friends give each other on Purim.

The one major design flaw: my mom’s hamentaschen were way better than everyone else’s. In the weeks before Purim started, I’d watch my mom make enough hamentaschen to feed a small army – but by the end of Purim, we’d have only one small box left, and lots of slightly-less-delicious hamentaschen from friends. Call me biased, but every year, I became something of a hoarder, finding and saving my favorite (poppy!) cookies before they were gone for another year.

Why not make more? Because “these hamentaschen came together in a flash!” said no one, ever. But the fruits are worth the labor. And while I always make some poppy seed filling for myself and the three other people who enjoy it, this year, I’ve found a real crowd-pleaser: raspberry chocolate filling.

(For those of you who looked at this picture and balked, fret not! Shortcuts after the jump.)


The filling isn’t a sauce, but it isn’t jam, either. Cathy, who shared a Christine Ferber recipe that I then adapted for this purpose, calls the mixture “chocolate raspberry whatever.” It’s a fitting name for an indescribable but very good thing. One batch will fill about 50 hamentaschen, but if you find yourself sneaking spoonfuls of the stuff straight, don’t say I didn’t warn you.

The easiest way to make chocolate raspberry whatever is to mix a jar of raspberry jam with the listed amount chocolate and a squeeze of lemon juice. If you’re in the mood for some fussing, you won’t regret making the riff on Cathy’s recipe that I share below.

I’m planning to take a couple three-pointed cookies in to work this week, if only to elicit the legitimate questions, “whaaa?” and “why not just make sandwich cookies?” Because then it wouldn’t be Purim. (Though, this recipe would make a damn good sandwich cookie. If you try that out, give a shout in the comments.)

GIVEAWAY RESULTS! Thanks to everyone who participated in last week’s Shabby Apple giveaway. I picked a random number using the random number generator, and the result is below:

Of the 31 comments not including duplicates and mine, lucky #22 won – congratulations Laura! The lovely folks at Shabby Apple will get in touch with you shortly.

Onward: let’s make some hamentaschen.

Raspberry Chocolate Hamentaschen
adapted from my mom and Mrs. Wheelbarrow
Makes 75 cookies

the dough:
10 1/2 tablespoons butter
1/2 cup sugar
1 large egg
1 teaspoon vanilla extract
zest of 1 lemon
1 teaspoon baking powder
1/2 teaspoon salt
2 1/4 cups flour, plus another 1/2 cup for rolling out the dough

For the filling:
12 oz. frozen raspberries
1/2 cup sugar
juice of half a lemon
3 oz. bittersweet chocolate

First, make the sauce: Put the raspberries in a microwave-safe bowl, and heat until raspberries have thawed and exuded their liquid, about 2 minutes. don’t stir the berries at all. Just let them heat up and let out their liquid. Once raspberries have thawed, strain them and either discard the liquid, or save it for another purpose.

If you want an extra-smooth filling, pass the raspberries through a food mill. This is totally not necessary.

Put the raspberries, sugar, and lemon juice into a medium pot, and heat on medium heat for a few minutes, until the sugar dissolves. Remove from the heat, and, if you didn’t pass the raspberries through a food mill earlier, use a fork to mash them up now.

Add in the chocolate, return the pot to the heat, and bring just to a simmer, stirring frequently. Simmer for about 5 minutes, stirring frequently, until sauce has thickened slightly and is uniform in texture. Remove from the heat, transfer to a bowl, and either set over an ice water bath (which will cool the sauce in 10 minutes flat) or transfer to the fridge for 1 hour.

Make the dough: In the bowl of a stand mixer, cream butter and sugar for about 1 minute on medium speed. Add the egg and lemon zest, and mix 1 minute more, scraping down the bowl a couple times in between.

In a separate bowl, combine baking powder, salt, and flour. Add the dry ingredients to the butter mixture, and mix on low speed just to combine.

Gather the dough into plastic wrap or a plastic bag, compress into a solid disk, and refrigerate 30-45 minutes (much longer, and it’ll be tough to work with).

Preheat the oven to 375 degrees and line 2 large baking sheets with parchment paper or silpat.

Sprinkle a work surface liberally with flour, and roll out the dough to 1/8-inch thick. Use a 2.5-inch cutter to cut disks of dough, and immediately plop the disks onto the lined baking sheet. When the work surface is floured, the disks will pop right out when you pull up the cutter. If not, don’t worry – just use a bench scraper or metal spatula to lift the disks and put them onto the baking sheet. Don’t worry about spacing the disks evenly; these hamentaschen don’t need much breathing room, and folded hamentaschen take up much less space than the disks.

This dough has very little liquid, so it lends itself well to re-rolling scraps. I generally work with half the dough at a time, and refrigerate the bunched scraps from one round while I bake the next batch. My oven only fits one of my cookie sheets at a time, but if yours fits multiple, feel free to shape and bake these in fewer batches than I did.

Once you’ve got a baking sheet full of disks, prepare your workstation: bring over your cooled filling and two small spoons, fill a small bowl with water, and get out a pastry brush.

Put a scant teaspoon of filling into the center of each disk. Use the pastry brush to brush water along the edge of each disk, and then use your thumbs and pointers to fold each disk into a triangle shape (see here for pictures).

Bake cookies for 15 minutes, until tops are slightly golden. Remove from the oven and let cool for 10 minutes before transferring. Meanwhile, fill your second sheet with cookies. By the time round 2 is ready to bake, round 1 will be cool enough to transfer, and that baking sheet will be free for batch 3.

Hamentaschen will keep in an airtight container for at least a week, probably more. They also freeze very well.

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1 Natasha February 19, 2013

I’ve never had hamentaschen before, but they look so pretty and the raspberry chocolate filling sounds delicious!

2 Hunny@SealedWithACookie February 19, 2013

Filling sounds really good, I love fruit and chocolate.

3 dena February 19, 2013

I love love LOVE chocolate raspberry rugelach, so hamantaschen with the same filling must be total heaven!

4 rivka February 20, 2013

Good call – this filling would be amazing in rugelach, incidentally.

5 Astheroshe February 20, 2013

We ate this cookies all the time!-my favorite as a kid with the prune and apricot. . I have my aunts recipe. I’m not sure exactly the connection i have to the Jewish religion sine I was raised Catholic – but we did eat these every Christmas lol .thanks for sharing the different filling . .

6 rivka February 20, 2013

glad you’ve enjoyed them!

7 Lisa February 20, 2013

These look wonderful! I am going to make them this afternoon! They will go great with a good cuppa tea! Thanks for sharing.

8 rivka February 20, 2013

Hope you enjoy them!

9 ISM February 20, 2013

Chag Semeach Rivka; thank you….these look great….chocolate & raspberry is my favorite. However, what kind of chocolate: unsweetened, semi-sweet, bittersweet…..or doesn’t it matter. I will pass this on to my daughters; I never make hamentachen….I count on shalich manot. Speaking of….are you planning on sharing a recipe for poppy seed cookies? My mother made batches and batches of poppy seed cookies and hamentachen for shalich manot then brought packages to those who were infirmed. I miss those poppy seed cookies.

10 ATG February 21, 2013

ANy tips for making sure the corners stay pinched together? Do you ever have a problem with this?

11 rivka February 21, 2013

brush water (or egg, if you prefer) around the inside edge of the disk before folding up. Works like a charm. When I make my mom’s, none of them open. I did try a certain other recipe last night (a double batch! Serves me right) and wound up with 50 thumprint cookies.

12 Rivki Locker February 21, 2013

I made these this evening and they are wonderful. I found the dough difficult to work with. I couldn’t get it thin enough. They still came out delicious but I only got about 20 cookies and they are definitely thicker than yours. Any thoughts on where I went wrong? the dough was crumbly and really hard to roll out. And, when I pinched them, a few of the cookies completely fell apart.

13 rivka February 22, 2013

Hmm, that’s so strange. I’ve never had them entirely crumble, but my best guess is that your eggs were smaller than mine or your cups of flour more (by weight) than mine. If the dough gets very very crumbly, don’t hesitate to add water by the tablespoon until it reaches a workable consistency.

14 Karyn February 25, 2013

These were amazing!

I had to use the water-by-the-bit a couple of times to keep the dough workable, I suspect my egg was too small.

My only question… when does the vanilla get added?

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