Rugelach (especially these chocolate cherry rugelach) are the perfect way to say “I love you.” Whether the gift is motivated by romance, friendship, the desire to provide solace, rugelach provide fit the bill. Making these tiny treasures, hand-rolled and filled with sweets, is like offering someone a piece of your heart.

Big or small, chock full of tidbits or simply rolled with a slick of jam, they’re a joy to make and give, plus they are pretty wonderful to eat. 

These are chocolate and cherry filled because it’s close to Valentine’s Day and I love that combination. I’ve posted about rugelach before, as part of the Tuesdays with Dorie baking group. That time the filling was apricot-based filling and the dough was sweeter and smoother than this one. There are endless variations on filling and even recipes that use yeast in the dough. I love homemade rugelach so much I’m tempted to try at least a few more versions soon.

No matter which recipe you use, these 3 handy rugelach-making tips should help:

1. The dough needs time to rest/chill, as do the formed rugelach before baking, so count on at least 3-4 hours total resting time, if not more.
2. Use a silicone mat or waxed paper lightly floured when rolling out the dough. The crescents come off the mat or paper more easily than the counter and if the dough gets too soft after rolling it into the large, thin circle, you can lift the mat or paper to refrigerate the dough for a few minutes, firming it up before cutting and rolling the individual rugelach.
3. The smaller the pieces of filling, the easier it is to roll the individual slices of dough. Concentrating the filling toward the outer part of the circle also helps.

Chocolate Cherry Rugelach

Servings – 32 pieces    Cost – $5

Ingredients

Dough

• 1 cup flour
• ¼ teaspoon salt
• 4 ounces (½ package) cream cheese, chilled and cut into 4-6 pieces
• 8 tablespoons (1 stick) butter, chilled but into 6-8 pieces

Filling & Wash for Tops Before Baking

• ¼ cup red jam, preferably cherry
• ¼ cup (about 1.5 ounces) finely diced frozen or fresh cherries
• ¼ cup (about 1.5 ounces) finely chopped dark or semi-sweet chocolate (or mini-morsels)
• ¼ cup (about 1.5 ounces) chopped slivered or sliced almonds
• 1- 2 tablespoons sugar (optional, not pictured)
• 1 egg mixed with 1 teaspoon water (not pictured)
• 1-2 tablespoons sugar or cinnamon and sugar (not pictured)

Equipment

• Measuring cups
• Measuring spoons
• Bowl and 2 knives or pastry cutter or food processor
• Plastic wrap for refrigerating dough
• Chopping board
• Knife
• Pastry brush or spoon
• Small bowl or ramekin
• Small pot (if heating jam on stovetop)
• Pizza cutter (optional)
• Silicone mat or waxed paper
• Parchment or silicone-lined cookie sheets
• Metal spatula
• Wire rack

Preparation

• Mix the flour and salt. Add the chunks of chilled butter and cream cheese. Pulse those ingredients in the food processor until they form soft, cheese curd-like balls. Don’t overmix to the point where the dough sticks all together. (Mixing by hand with a pastry cutter or 2 knives works, it just takes longer.) Dump the dough “curds” onto the baking mat or waxed paper and divide them in half. Form each into a ball; you should still see bits of unmixed butter and cream cheese laced through the dough. It’s fine if the dough balls are crumbly. Wrap them in plastic wrap, form each into a 4-6 inch disc, and refrigerate them at least 3 hours – longer, even overnight, is better.

• On a lightly floured mat or waxed paper, roll one chilled disc into a thin circle about 10-12 inches in diameter. (Check out the fabulous marble rolling pin my sister-in-law gave me last week!) If the dough is too crumbly, you can knead it for a minute or two, as long as you don’t heat it up. The wider you roll out the circle, the thinner the dough (which makes it a bit more difficult to roll), but also the more elegant the crescents. Although perfect edges are lovely, they aren’t essential as the edge doesn’t show once the chocolate cherry rugelach are rolled. 

• After heating the jam slightly, brush or spread it onto the circle with the back of a spoon. (I microwaved the jam for 30-45 seconds, which loosened it enough to easily brush it over the dough.) Sprinkle the chopped/diced toppings and add optional sugar if you want it to sweeten it a little. (My frozen cherries were rather tart and I used dark chocolate. If you use sweeter cherries and/or semi sweet chocolate, you may find the toppings adequately sweet without extra sugar.) At the end, it looks like a sweet pizza. If you’re concerned about ease of cutting and rolling the slices, use less topping.

• Using a pizza cutter or sharp knife, cut the circle into quarters and each quarter into quarters again, so you end up with 16 thin slices of “pie.” Roll up one slice beginning at the wide end and working toward the center of the circle. Remove that rugelach and repeat the process with each slice. There is no need to be concerned if the chocolate cherry rugelach are slightly rough-looking or if filling oozes out, those features are part of their charm. 

• Place the rugelach on a silicone mat or parchment-lined pans with their points on the bottom to seal them so they don’t unravel. Refrigerate or freeze the rugelach for at least an hour. You can transfer frozen rugelach to a tightly closed freezer bag and keep them frozen for several months.
• Repeat the process with the second disc of dough.
• To bake: Preheat the oven to 375 degrees F. Brush the rugelach with the egg mixture and sprinkle them with sugar or cinnamon and sugar. I like to put a second pan underneath each pan to prevent the rugelach bottoms from burning. Bake for approximately 22-28 minutes. (You can bake them directly from the freezer; it just takes a few minutes longer than if they had been refrigerated.)  If you are baking two pans at the same time, rotate them midway during baking, from top to bottom and turn them each around, in order to promote even baking of all the individual rugelach. They are done when slightly puffy and golden brown. Remove to a wire rack for cooling.