Chocolate Cinnamon Fantails


I remember two things about New Year’s Day from my youth: First, the family loved to sit around on New Year’s morning and watch the Rose Parade. Second, my mom used to warn me that whatever I did on New Year’s Day would set the trend for the rest of the year. Although I know that her warning simply reflects an old European wive’s tale, it crosses my mind every New Year’s and makes me think about how I spend my day.

So, if the old wive’s tale holds any stock, January 1st determined that my year thus far is comprised of recuperating (still) from a sinus infection and awakening in the middle of the night (2 a.m. to be exact) and not able to fall back asleep for a couple hours. Does that mean, then, that my year will be filled with sickness and insomnia?! Yikes!

Well, at least I used that early early morning time to have a bowl of granola with milk and to read a few pages of a novel.

And later in the morning, I spent some time playing in the kitchen to create a New Year’s  morning treat. Uh oh, does that mean I’ll be eating sweets all year, too? So be it :  )

Using leftover dough and spice filling from cinnamon rolls I made the other day, I modified several recipes (Cinnamon Cream Cheese Rolls and Cinnamon Pull-Apart Bread and a few from other blogs) to create these delightfully scrumptious Chocolate Cinnamon Fantails.

I could eat these darn delicious treats all year long if my mom’s old wive’s tale holds any truth :  )


Chocolate Cinnamon Fantails

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Note: The dough can be in advance and stored in the refrigerator for about 3 days. It is much more pliable to work with after refrigeration; plus, it’s handy to have the dough ready to go in the morning. I suggest doubling the batch.



1 cup whole milk

1/4 cup vegetable oil

1/4 cup granulated sugar

1 1/4 tsp. active dry yeast

2 cups + 1/4 cup unbleached all-purpose flour

1/2 tsp. baking powder

1/4 tsp. baking soda

1/2 tsp. salt


  • 8 ounces bittersweet chocolate (I used Ghriadelli’s chips)
  • 1/4 cup sugar
  • 1/2 tbsp. cinnamon
  • 1/4 tsp. salt
  • pinch ground cloves
  • 3 tbsp. unsalted butter, room temperature


  1. For the dough: Heat milk, oil, and sugar in large saucepan over medium heat to just below a boil (that’s called scalding). Set aside and cool until warm, about 30-60 minutes.
  2. Once the milk/oil/sugar mixture cools to lukewarm, sprinkle the yeast on top and let it sit on the milk for one minute.
  3. Add 2 cups flour. Stir until just combined, then cover with a clean kitchen towel and set aside in a relatively warm place for one hour for dough to rise.
  4. After one hour, remove the towel; add the baking powder, baking soda, salt, and the remaining 1/4 cup of flour. Stir thoroughly to combine.
  5. Dough can be used right away, but it will be sticky at this point. Or, refrigerate for up to 3 days, punching down the dough if it rises to the top of the bowl. (Dough is much easier to work with when it has been chilled for at least an hour or so.)
  6. For filling: In a food processor, combine chocolate chips, sugar, cinnamon, salt, and cloves; pulse until chocolate is chopped into small, coarse pieces.
  7. Cut butter into small pieces, about 1/2 inch squares. Place in food processor and pulse until it is mixed in with chocolate, sugar, and spices.
  8. To assemble rolls: When ready to assemble rolls, preheat oven to 350 degrees F. Grease the wells of cupcake tins.
  9. On a generously floured baking surface, roll the dough into a large rectangle, about 14 X 18 inches (my dough was about 1/8 inch thick). I find it easiest to roll from the center toward the ends.
  10. Distribute filling mixture evenly onto rolled-out dough. Use your hands to press filling into dough, or cover with plastic wrap and gently roll over it with the rolling pin.
  11. Use a pizza cutter (easiest method) or knife to slice dough into 2 inch strips (either direction works). Stack 2-3 strips, then cut into 2 inch pieces again.
  12. Stack about 6-7 squares, turning last one so chocolate mixture faces downward. Place stacks into greased wells of cupcake tins.
  13. Bake at 350 degrees F for 20-25 minutes, until golden brown on top. Cool slightly, then remove from pan and serve.

Yield: about 10-12 fantails, depending on how many slices you stack to make each one

SOURCES: adapted from & inspired by The Pioneer Woman, Joy the Baker, Brown-Eyed Baker, Naturally Ella, and Annie’s Eats via Smitten Kitchen

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