Make sweet or savory challah-taschen for your Purim Seudah. With surprise fillings inside, they’ll be a huge hit! Here’s how to do it.
About 4 years ago, not long after I began my challah business, I came up with this idea as a fun twist on the traditional hamantashen. Since challah is kind of my “thing,” it was really a no brainer to turn this iconic Jewish cookie into stuffed challah-taschen.
The possibilities are endless. Over the years, I’ve been stuffing my challahs with everything from roasted garlic to chocolate ganache (*swoon*). Whether your family likes savory or sweet, you really can’t go wrong with this concept. Below are some of my favorites, along with step-by-step instructions on how to make sure your challah-tashen hold their shape and give your Seudah table a little extra “wow” this Purim.
Tip: These can made into individual sized “tashen,” to serve as a place setting for every guest. Alternatively, you can make a giant version with a full-sized challah dough to use as an eye-catching centerpiece. Since we all have our favorite challah recipe or flour we prefer, feel free to use your own challah dough to make these (or even a store bought frozen dough will do!).
- 1 recipe of your favorite challah dough
- 1 filling recipe (options below)
- 1 egg beaten with 1 Tbsp water
- For individual sized challah-tashen, divide your dough into 3 ounce portions (I like to do this before my dough rises for the first time). For large challah-tashen, divide dough into 24 ounce (1 ½ pound) portions. A 5 pound batch of dough should give you about 6 large portions or 48 individual portions.
- Form each piece of dough into a ball and place on parchment-lined baking sheets. Spray tops and sides with cooking spray and cover tray with plastic wrap. Place a clean kitchen towel over the top (this keeps the heat in and helps the dough to rise) and allow dough to rise for about 2 hours (less if your kitchen is warm, more if it’s on the colder side) or until doubled in size. (Note that egg-free recipes tend to rise much faster, and are often stickier than egg doughs. Adjust your rising time or flour as necessary to make sure your dough is easy to work with. If it’s too sticky it may be harder to fill and shape. I also do not like to flour my work surface, as the dough will not pinch together well, and you may end up losing your fillings. I prefer to gently oil my hands as necessary if the dough is a little too sticky.)
- Preheat oven to 350°F. Line additional baking sheets with parchment paper. Place one piece of dough onto a clean work surface, and using the palm of your hand, gently flatten dough into a about a 6-inch circle (for the larger dough, I use a rolling pin, and roll into about a 15-inch circle). Your flattened dough should be about a ½ inch thick. For small sized dough, place roughly 2-3 tablespoons of your desired filling into the center of your flattened dough circle, leaving about a 1-inch border. (Use your judgement when it comes to the amount of filling. You want a nice dough to filling ratio, but if you overfill your dough, it will split and seep out.)
- Fold the dough up on 2 sides and pinch to form one corner. Fold up the third side and pinch additional 2 corners to form a triangle (just like you would a traditional hamantash). Continue pinching all 3 corners all the way up to the center to seal filling in completely. Once tightly sealed, carefully flip your dough over so the sealed side is face down. Feel free to manipulate dough as needed to form a neat triangle.
- Repeat with remaining dough and place on prepared baking sheets. Be sure to leave enough space for dough to rise (I can usually fit about 10 small or 2 large doughs per baking sheet). Cover challahs once more with a kitchen towel and allow to rise an additional 45 minutes to an hour (depending on the heat of your kitchen – again, they should double in size).
- Brush each challah with egg wash and sprinkle with suggested toppings (ideas below). Bake small challah-tashen for 22-30 minutes and large for 35-45 minutes (this may vary depending on which filling/topping you are using – crumb toppings may take slightly longer to bake), or until browned on top and edges. Rotate your pans ⅔ of the way through baking. Transfer to baking racks to cool. Enjoy as an appetizer, accompaniment or even as dessert!
Caramelized Onion Filling
These onions can be made up to 3 days in advance and stored in the fridge in an airtight container. These can also be frozen for up to 3 months! Set aside a few thin slices of raw onion to top your challah with. This will help you to remember what’s inside!
- 4 large sweet onions (such as Spanish or Vidalia), thinly sliced lengthwise, or diced
- 2 sprigs fresh thyme
- 1 tablespoon balsamic vinegar
- 1 tablespoon brown sugar
- 2 tablespoons olive oil
- 2 teaspoons Kosher salt
- black pepper, to taste
- Sliced raw onion
- In a large skillet, heat oil over medium heat. Add onions, salt, and thyme, and allow to sweat for 10-15 minutes, stirring every minute or so to allow all the onions to reach the heat and break down.
- Once onions have released most of their moisture, the natural sugar in the onions will begin to caramelize and they will slowly start to brown. Reduce heat to low and keep stirring often for an additional 15-20 minutes, until they turn a deep golden color and become almost sticky.
- Add vinegar and brown sugar and allow vinegar to evaporate and sugar to melt into the onions. Season with black pepper and additional salt if desired. Set aside to cool.
Roasted Garlic Filling
Save any extra roasted garlic to use for everything from mashed potatoes, to a challah spread, or in an endless number of savory recipes. This will also stay well in the freezer in an airtight container for up to 3 months.
- 1 large bag of peeled garlic (I buy the Costco sized bag)
- 3 tablespoons olive oil
- 2 whole sprigs fresh rosemary
- 2 additional sprigs fresh rosemary, leaves removed from stems, and finely chopped (for topping)
- Coarse sea salt (for topping)
- Fresh rosemary
- sea salt
- Place a large piece of foil on top of a metal baking sheet. Place peeled garlic on top of foil and drizzle with olive oil. Toss well and top with rosemary sprigs. Wrap foil around garlic to form a sealed pouch. Roast for about 1 hour and 15 minutes, or until soft and slightly browned.
Chocolate Ganache Filling (Pareve)
A ganache is usually made with heavy cream, so I like to use canned coconut milk, because it has a similar fat content to cream (but it’s a much healthier fat). Also, the ratio of coconut milk to chocolate does not make the entire ganache taste like coconut. My kids could eat this by the spoonful if I let them.
- 8 ounces good quality semi-sweet chocolate, chopped, or chocolate chips (I love Enjoy Life mini chocolate chips or mega chunks)
- ½ cup coconut or almond milk
- 1 teaspoon instant coffee grinds, dissolved in milk
- ¼ teaspoon ground cinnamon
- 2-3 pinches of sea salt or kosher salt
- 1 recipe Funfetti Topping (recipe below)
- Put first 4 ingredients into a heatproof bowl (I recommend a metal mixing bowl, but a Pyrex will work as well), and set over a pot of simmering water on the stove. As the milk heats it will begin to melt the chocolate. Stir until chocolate is fully melted and ingredients are well combined, and no lumps remain. Be patient! If you try to heat your ingredients too quickly you will burn your chocolate.
- Remove from heat, add a couple of pinches of salt and stir well (salt brings out the flavors in anything you cook, especially sweet things!). Allow ganache to cool for at least 1 hour in the fridge. You can also make this ahead! This ganache freezes well for at least 3 months, and will also stay in your fridge in an airtight container for at least 2 weeks. Bring ganache to room temperature before using, to make it easy to spread.
Funfetti Crumb Topping
These can also be made ahead and refrigerated or frozen until ready to use. I store extra crumbs in freezer bags in my freezer, so I always have some on hand when I want to top a challah, fruit crisp or even cupcakes before putting in the oven!
I know this recipe calls for margarine, which is definitely not a healthy fat, but margarine/butter gives a much better crunch to your crumbs than oil does, so I do not recommend swapping the margarine for oil. Everything in moderation!
- 6-7 tablespoons cold margarine or butter, cut into small cubes
- 1 cup all-purpose flour
- 1 cup sugar
- ½ teaspoon fine sea salt
- 3 tablespoons rainbow sprinkles
- Combine first 4 ingredients in a bowl and using a pastry cutter, fork, or even your fingers, cut “butter” into flour until it becomes the texture of crumbs. Add sprinkles and gently toss together until evenly distributed.
Lotus Cookie Butter Crunch
- 1 jar Lotus cookie butter (for filling)
- 6-7 tablespoons cold margarine or butter, cut into small cubes
- 1 cup all-purpose flour
- 1 cup sugar
- 1 teaspoon King Arthur Speculaas Spice (available on Kingarthurflour.com)
- ½ teaspoon fine sea salt
- Lotus cookies, broken into small pieces
- Prepare the topping. Combine first 5 ingredients in a bowl and using a pastry cutter, fork, or even your fingers, cut “butter” into flour until it becomes the texture of crumbs.
- Add broken cookies and gently toss together until evenly distributed.
Additional Filling & Topic Suggestions:
*Fill with Nutella or pareve hazelnut chocolate spread and topped with classic crumbs or rainbow sprinkles.
*Fill with creamy peanut butter and raspberry jam (serve warm for a PB&J on steroids!).
*Fill with apricot pie filling (I love Solo brand, but note it is labeled DE), brush challah-taschen with some more apricot filling, and sprinkle with almonds.
To make traditional hamantaschen, check out this post!
Thanks Kayla! Made them and they look beautiful!
I love this idea. Can you give us some idea of how much dough (in weight) you used for each individual challah-tashen.
The measurements are in the instructions. About 3oz for each. The large one is 1.5 lbs.
These sound amazing – have you frozen them baked? Assume they defrost fine like any challah?
I want to make the large tashen. How much chocolate filling do I put inside?
How long do I bake it?
These are likely a mezonos ask your LOR
Any meat options?