As part of last weekend’s baking extravaganza, I made several batches of hamentashen. For those of you who don’t know (and you wouldn’t be alone), hamentashen are triangular-shaped cookies that are typically filled with prune, apricot, or raspberry jam. They also happen to be one of my favorite things ever.

Now I will warn that hamentashen are fairly time-consuming as far as cookies go. The classic dough recipe I use is easy enough and takes no time to throw together, but the process of rolling out the dough, filling it, and shaping it requires a decent amount of time and patience. And the dough sometimes doesn’t like to cooperate. And the cleanup is atrocious (imagine sticky, caked-on dough particles all over your countertop and flour everywhere). But the end result is undeniably delicious, so if you’re up for the challenge, go ahead and make these one day. If anything, the people you share them with will get a kick out of the fun shape.

I like to make a variety of hamentashen, including some non-traditional variations. This year’s batch included classic prune, Nutella, apple-caramel, peanut butter and jelly, peanut butter and chocolate chip, and pumpkin. To create this assortment, I used three separate dough recipes, the most challenging of which is by far the classic one.

As far as my favorite version of the hamentashen goes, that’s hard to say. I really enjoyed the peanut butter and jelly combination, but there’s just something about classic prune-filled hamentashen that makes me keep going back for more. It’s a good thing I made almost 200 of these bad boys over the weekend. No, I’m not kidding. I gave most of them away but kept a few dozen on hand for myself…most of which are already gone…

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Classic Hamentashen (my mom’s recipe)
5 eggs, plus one more for brushing on the dough
1 and ½ cups vegetable oil
3 tsp baking powder
1 and ½ cups granulated sugar
¾ cup orange juice
6 cups AP flour
1/8 tsp salt
Water as needed, up to ¾ of a cup

1. Combine eggs, oil, baking powder, sugar, orange juice, flour, and salt in a large mixing bowl. Use a spoon and then your hands to form a dough that is soft but not too sticky. Add water as needed if the dough is too crumbly. If you end up incorporating too much water, you’ll need to compensate by adding more flour.
2. Cover the dough with plastic wrap and refrigerate for 30 minutes.
3. Preheat your oven to 350 degrees once the dough has come out of the fridge. Prepare as many baking sheets as you can by lining with aluminum foil and lightly greasing. (This recipe makes anywhere from four to six dozen hamentashen depending on big you make them, so unless you’ve got an endless supply of cookie sheets, prepare to bake these in several batches.)
4. Divide the dough into four sections and roll it out on a well-floured surface to ¼ inch thickness.
5. Cut the dough into circles using either a cookie cutter or a regular drinking glass (the latter is my preferred method). Place the circles on the prepared baking sheets.
6. Place a small amount of your desired filling in the center of each circle. Be careful not to overfill your hamentashen.
7. Form the circles into triangles by folding the dough over one side at a time. Lightly pinch each corner to seal the hamentashen.
8. Lightly brush each formed hamentashen with beaten egg.
9. Bake for 20-30 minutes, or until the tops are golden brown. Baking times can vary based on the size of your hamentashen as well as your oven, so be sure to check on them frequently once you hit the 20-minute mark.
10. Let the hamentashen cool on their baking sheets for 2-3 minutes, then transfer them to a rack to cool completely.

I used this classic recipe to make my prune, Nutella, and caramel-apple hamentashen. For the caramel apple, I simply used apple pie filling for the cookies and then drizzled them with a caramel sauce I made by heating about 15 Kraft caramel squares with a few teaspoons of milk.


Peanut Butter Hamentashen

2 sticks of unsalted butter at room temperature
3 cups Ap flour
1 and 1/2 cups granulated sugar
2 large eggs
2 and 1/2 cups smooth peanut butter
1 and 1/2 teaspoons salt
1 teaspoon baking powder
1 teaspoon pure vanilla extract

1. Using a hand or stand mixer, beat the butter and sugar on medium until the mixture is light and fluffy. Beat in the eggs one at a time. Add in the peanut butter and beat on medium for 2-3 minutes, or until well-combined.
2. Whisk together your flour, salt, and baking powder; then add to the peanut butter mixture and beat at low-medium speed until well-combined. Add your vanilla and mix well.
3. Cover the dough and refrigerate for 30-60 minutes. Then follow the steps above to roll it out and form it into triangles. (No need to use an egg wash for this dough).
4. Bake for 18-22 minutes at 350 degrees, or until the tops are golden brown. Follow the instructions above for cooling.

I filled my peanut butter hamentashen with grape jelly, strawberry jelly, and chocolate chips. I also threw in a couple of smashed-up Butterfinger bars as a filling. Feel free to get creative by adding raspberry jam, Nutella, white chocolate, or your favorite crushed-up candy bar.


Pumpkintashen (Pumpkin Hamentashen)
Recipe from allrecipes.com

3/4 cup unsalted butter
1/2 cup packed brown sugar
1 tablespoon orange zest
1/2 cup pumpkin puree
1 egg yolk
1 tsp vanilla extract
2 and 1/4 AP flour
1/4 teaspoon ground cinnamon
1/4 teaspoon ground ginger
1/4 teaspoon ground nutmeg
Pinch of salt

1. Cream together the butter, brown sugar, and orange zest.
2. Stir in the pumpkin.
3. Add the egg yolk and vanilla; mix well.
4. Sift together the flour, cinnamon, ginger, nutmeg, and salt; stir into the pumpkin mixture.
5. Cover the dough with plastic wrap and chill in the fridge for 30 minutes.
6. Follow the steps above to roll out the dough and form it into triangles. (No need to use an egg wash for this dough).
7. Bake at 375 for 20-25 minutes.
8. Follow the instructions above for cooling.

I filled my pumpkintashen with chocolate chips, white chocolate chips, and butterscotch chips. I think a sweet cinnamon-cream cheese filling would taste fantastic with these, but I kept things simple and stuck to the chips.


Peanut Butter and Jelly Bars

Sometimes it pays to keep things simple flavor-wise. Case in point: the classic peanut butter and jelly combination. Growing up, PB&J sandwiches were a steady part of my school lunch rotation; and while I suppose I enjoyed them, they certainly didn’t stand out at the time as anything particularly special. But as I got older, I began to develop a fondness for PB&J. Maybe it’s because your coworkers look at you funny when you’re sitting around the break room table and they’re all eating their tandoori chicken takeout while you’re eating something they haven’t tasted since 1987. Or perhaps it’s because there’s just something about the awesome flavor combination that simply brings back memories of being a carefree kid.

Either way, peanut butter and jelly is a winner in my book, so it was only natural take the concept one step further by turning it into dessert. I found this Martha Stewart recipe and decided to give it a go, and the result was a batch of peanut butter and jelly bars that are good enough to make any adult feel like a kid again.

For some reason, these bars took a little longer to make than I initially expected. The peanut butter dough was really thick, and so I had to keep scraping down the sides of my mixer bowl and adjusting the speed up and down. And then it took me awhile to chop up the peanuts and make the crumbly dough topping, but that’s partly because for some strange reason, I love the feeling of balled-up dough in between my fingers and probably wasn’t in a particular rush to get the process over with.

This recipe makes a nice amount of PB&J bars—which means you’ll probably have enough left over to divvy up among your coworkers in exchange for their promise to stop mocking you for your peanut butter and jelly lunches, at least for the foreseeable future.


Peanut Butter and Jelly Bars
Recipe from Martha Stewart

1 cup (2 sticks) of unsalted butter, room temperature, plus more to butter the pan
3 cups of AP flour, plus more for the pan
1 and 1/2 cups granulated sugar
2 large eggs
2 and 1/2 cups smooth peanut butter
1 and 1/2 teaspoons salt
1 teaspoon baking powder
1 teaspoon vanilla extract
1 and 1/2 cups of your favorite jam flavor (I used strawberry and classic grape—I’ll explain)
2/3 cup salted peanuts, roughly chopped

1. Preheat your oven to 350 degrees. Grease a 9-by-13-inch pan with butter, and line the bottom with parchment paper. Grease the parchment, and coat inside of the pan with flour; set aside.
2. Place the butter and sugar in the bowl of an electric mixer fitted with the paddle attachment. Beat the mixture on medium-high until fluffy, about 2 minutes. Add eggs and peanut butter; beat on medium until well-combined (this took me about 3-4 minutes; the original recipe estimates 2).
3. Whisk together the salt, baking powder, and flour. Add dry ingredients to mixture and beat on low-medium speed until well-combined (this took me another 3-4 minutes, alternating between speeds).
4. Add vanilla and mix until incorporated.
5. Transfer 2/3 of the mixture to your prepared pan, and spread evenly.
6. With a spatula, spread jam on top of peanut-butter mixture. **
7. Crumble remaining peanut butter mixture on top of the jam layer, and sprinkle with peanuts.
8. Bake until the tops turn golden, about 45-55 minutes. (The inserted toothpick test doesn’t really work here because the jelly layer is always going to be gooey.)
9. Transfer to a wire rack and make sure to cool these completely before cutting into them. I stuck them in the fridge to set for about an hour and then left them out on my counter for another hour before slicing them up—and that totally did the trick.

**I wanted to see what these would taste like with both strawberry and grape jelly, so I decided to put strawberry over half of the base and grape over the other half. While I don’t think the two versions taste remarkably different from one another, I do like the way the strawberry version gives you a touch of tanginess while the grape bars really take you back to that classic old-school flavor. I also wound up with a few hybrid bars as a result of the strawberry and grape jellies melting into each other in the middle of the pan during the baking process, but happily, those tasted just as good as their individual strawberry or grape counterparts.