This chocolate cinnamon rugelach recipe gives you soft, flaky, sweet pastry you won’t soon forget! With only 20 minutes of prep, and 15 minutes in the oven – these are a quick family favorite.
When describing a rugelach to people who haven’t tried them, I always say they are a blend of both a cookie and a pastry. These chocolate cinnamon rugelachs have a crispy cream cheese dough and a smooth chocolate and cinnamon filling. Brushed with sugar, these stunners are absolutely addicting!
I also love that these freeze really well, so you can make them in advance easily and enjoy throughout the year. The prep for these is only about 20 minutes, and after an overnight chill, these chocolate cinnamon rugelach puff up in the oven after about 15 minutes.
What is a chocolate cinnamon rugelach?
This traditional Jewish pastry is found in cafes all over the world, and comes in tons of varieties. I love learning about the history of the treats I make, and this one has a lot of rich tradition as well as arguments over the meaning of the name.
In Yiddish, it loosely translates to “little twist” (which may be the most precious pastry name I’ve ever heard). Alternatively, some say that the root words are closer to “royal” in reference to its rich flavor.
The earliest recipes for this included a yeasted, or occasionally sour-cream based, dough. Since the 1940s, cream cheese dough has become popular, and it is what we use here in the chocolate cinnamon rugelach. This type of dough gives a rich, creamy base for a variety of fillings both savory and sweet.
For the dough, you will need butter, cream cheese (at room temp), flour, salt, powdered sugar, an egg yolk, vanilla, and almond extract.
The chocolate cinnamon rugelach filling needs milk chocolate chips, cinnamon, an egg, sugar, sea salt, and cinnamon.
Note that the recipe initially calls for sanding sugar, which has larger crystals and a bit of crunch to it. If that isn’t available to you, granulated works great too!
How to Make // The Steps
- First, with an electric or stand mixer, whip the butter and cream cheese until smooth.
- Next, add flour, salt, powdered sugar, egg yolk, vanilla and almond extracts. Mix until the dough just starts to come together. Be careful not to overwork the dough, and don’t worry if there are small bits of butter throughout.
- Turn the dough out and separate into two discs and wrap tightly with plastic wrap.
- Let the dough chill in the fridge for at least four hours – but I prefer overnight!
- When it’s time to bake, take your dough out of the refrigerator and let it sit to room temperature.
- While the chocolate cinnamon rugelach dough sits, line two baking sheets with parchment paper.
- Using a double boiler, or the microwave (in 30 second bursts), melt your chocolate until smooth.
- Add in the cinnamon and mix.
- Dust your work space with flour and roll the dough out to a circle about 1/16th of an inch thick.
- Spread the filling mixture evenly across the dough, almost reaching the edges. I find that an offset spatula is easiest for this process, and it doesn’t tear the dough.
- With a pizza cutter, cut the dough in half, then half again. (I love this compact one for baking!) You will now have four pieces, each of which you cut into another four. This gives you a total of 16 pieces of dough.
- Shape your dough like a crescent roll, starting from the longest edge.
- Once rolled, put the chocolate cinnamon rugelach on the baking sheet and slide them into the fridge for 30 minutes to chill.
- When you’re ready to bake, preheat your oven to 350 degrees F.
- Once chilled, brush egg wash over the chocolate cinnamon rugelach and dust on the cinnamon sugar combination.
- Bake the chocolate cinnamon rugelach for 15-18 minutes, or until golden brown
What makes this chocolate cinnamon rugelach so good?
I love a good pastry, and I have never met a rugelach I didn’t like! But this recipe stands out for a few reasons:
- The chocolate and cinnamon combination is not as common as I think it should be, and this is a great way to try it out!
- Rolling these is really fun, and a great family activity because even tiny hands can turn these into little twists!
- I really enjoy baking something that comes with a story, and the history of these chocolate cinnamon rugelachs is a great reminder of why it is so important to pass down recipes while also modernizing and updating them.
Storing and Freezing your Chocolate Cinnamon Rugelach
Here are a few ideas for storing these beauties:
- To have fresh rugelach on hand whenever you want, you can freeze the rolls before they are baked. Once they are twisted up and ready to go, line an air-tight container with parchment paper and carefully stack your chocolate cinnamon rugelach between more layers of parchment paper.
- No need to thaw these out – because you can bake these from frozen! All you have to do is reduce the baking temperature to 350 degrees, and leave it in for an additional 3 to 4 minutes.
- I like leaving the baking instructions on a post-it attached to the container. This makes it so easy when you crave one of these months after you make them!
- For an even fresher version of the cinnamon chocolate rugelachs, you can simply freeze the wrapped dough and pull them out when you’re ready. Because the chocolate is melted, I do not suggest trying to make the filling prior, as it won’t reheat properly and will dry out.
There are various combinations of rugelach worldwide, including some places where savory rugelach is gaining popularity. I may love these chocolate cinnamon rugelach, but there are a few combinations I am really excited about trying next:
- Apricot jelly and almond slices
- Orange preserves and pine nuts
- Chocolate hazelnut
- Berry jams and rosemary
- Cheddar and pecan
- Spinach and sun dried tomato
More Pastry Recipes //
- Crackle Top Cream Puffs
- Braided Cardamom Bread
- Cranberry Cheddar Scones
- Ham Cheddar and Rosemary Pinwheels
- Whole Wheat Spiced Pumpkin Muffins
Chocolate Cinnamon Rugelach
- 1 cup butter room temperature
- 1 brick 8-oz. cream cheese, room temperature
- 2 ¼ cups flour
- ¼ teaspoon salt
- ¼ cup powdered sugar
- 1 egg yolk
- 1 teaspoon vanilla
- ½ teaspoon almond extract
- 2 cups milk chocolate chips
- 3/4 teaspoon cinnamon
- 1 egg
- 2 tablespoons sanding sugar or regular sugar
- 1 teaspoon flaked sea salt
- Mix together butter and cream cheese in the bowl of an electric mixer until combined.
- Add flour, salt, powdered sugar, egg yolk, vanilla and almond extracts. Mix until the dough just comes together, being careful to not overwork the dough. It’s okay if there are still some pieces of butter.
- Turn the dough out, separate into two pieces, form into two disks, wrap in plastic wrap, and chill for at least 4 hours, preferably overnight.
- When ready to bake, remove the dough from the fridge and let sit at room temperature for 15 to 20 minutes.
- Line 2 baking sheets with parchment paper and set aside.
- Melt chocolate using a double boiler or microwave and mix in 1/2 teaspoon cinnamon.
- Dust your surface with flour and roll dough into a circle about 1/16th of an inch thick.
- Spread a generous amount of chocolate out to the edges of the dough and even out with an offset spatula.
- Using a pizza cutter, dive the dough in half, then quarters, and slice the quarters into 4 pieces. Roll up the dough from the longest edge, like a crescent roll.
- Place on a baking sheet and chill for 30 minutes.
- Preheat oven to 375°.
- Whisk egg. Combine sanding sugar, sea salt, and remaining cinnamon in a small bowl.
- Brush tops of cookies with egg wash and sprinkle with cinnamon sugar.
- Bake for 15 to 18 minutes or until golden brown.