Chocolate Cherry Rugelach

2012 is winding down, bringing us the last First on the First of the year. Thank you for joining us, whether you baked along, salivated over the photos and descriptions, or made the recipes we tried! Kate and I are looking forward to another year of culinary challenges and hope you will join us in executing them! The more, the merrier–there can’t be too many cooks in this virtual kitchen!

Chocolate Cherry Rugelach

Rugelach. I had a bad experience with rugelach before. Filling oozing out, messy little bites that were pretty darn ugly. Great idea, poor end product. (Or poor skills on my part–I’ll take ownership of that.) It’s taken me nearly 2 years to build the courage to attempt rugelach again. Something that should be so easy has gained epic pedestal status because of my inability to attain a satisfactory sweet with my last try. This is ridiculous!

Chocolate Cherry Rugelach

The making of the cookies themselves is fairly easy (though a tad messy, with all the flour on your counters). It’s the chilling of the dough that makes the task seem daunting. You need to add 90 minutes to your prep and baking times to accommodate hang time in the fridge; leaving this to the last minute, as I’m prone to do, is a recipe for disaster. Or a panicked crash on the couch for two hours, entirely in denial of the fate that awaited me. Whichever.

Chocolate Cherry Rugelach

Even done correctly, these are still messy. You’ll get cinnamon sugar and chocolate chips all over your counter. (Though I scooped the remnants up into my mouth–have to clean up, after all.) The preserves will ooze out of the cookies a bit. Cinnamon sugar will be everywhere, after you’ve sprinkled it on the cookies. In all this chaos, you’ll find that you really don’t care. It doesn’t matter. There are painstakingly perfect cookies, with intricately detailed royal icing…and then there are cookies like these. A little like you look when you wake up late and have no time to shower… yet brilliant. It doesn’t matter what they look like. It’s all about the flavor.

Chocolate Cherry Rugelach
Prep time
Cook time
Total time
Recipe type: Cookie
Serves: 48
  • 8 ounces cream cheese, softened
  • 1 cup (16 Tablespoons or 2 sticks) unsalted butter, softened
  • ¼ cup granulated sugar, plus 9 tablespoons
  • ¼ teaspoon kosher salt
  • 1 teaspoon vanilla extract
  • 2 cups all-purpose flour
  • ¼ cup light brown sugar, packed lightly
  • 2 teaspoons ground cinnamon
  • ¾ cup mini chocolate chips
  • 1 cup pecans, toasted and then finely chopped
  • ½ cup cherry preserves
  • 1 egg beaten with 1 tablespoon milk, for egg wash
  1. In the bowl of a stand mixer, cream the cream cheese and butter together until light and fluffy.
  2. Add ¼ cup of the granulated sugar, the salt, and vanilla extract, beating on medium-low for 3 minutes.
  3. On low, add the flour, beating until just incorporated.
  4. Flour a work surface and turn the dough out onto it, shaping into a disc. Cut the disc into 4 portions, wrap each in plastic wrap, and chill in the fridge for one hour.
  5. For the filling, in a medium bowl, mix 6 Tablespoons of the granulated sugar, all of the brown sugar, 1 teaspoon cinnamon, chocolate chips, and pecans.
  6. Flour a work surface, remove a dough disc from the fridge, and flatten it out until you have a 9-inch diameter circle.
  7. Spread 2 Tablespoons of cherry preserves over the disc and sprinkle ¼ of the filling (approximately ½ cup) over that, pressing the filling lightly into the dough.
  8. Using a pizza wheel, cut the disc into 12 triangles (cut into quarters first, then each quarter into thirds).
  9. Roll each triangle from the long side to the point, making a little crescent.
  10. Line 2 baking sheets with parchment paper and place the crescents on the prepared baking sheets, point side down.
  11. Place baking sheets in fridge for 30 minutes to chill (you can also freeze the cookies at this point and bake them off later).
  12. Preheat oven to 350 degrees Fahrenheit.
  13. Brush each cookie with the egg wash. Combine 3 tablespoons granulated sugar and 1 teaspoon cinnamon and sprinkle on the cookies.
  14. Bake on the middle rack of the oven for 15-20 minutes, or until lightly browned.
  15. Transfer to a wire rack to cool.

To ring in the new year, we’ll be making Swiss Rolls. Your interpretation, your twist, however you’d like to make them. For details on how to bake along with us, check out the First on the First tab above. If you don’t have a blog of your own, feel free to post your results in the comments on Kate’s or my blog post for Swiss Rolls–we’d love to hear about it! January 1st… be there!

And now…for all the other yummy rugelach!

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