• Cooking Time: 1 hour
  • Servings: 12
  • Preparation Time: 30 minutes


Caramel Filling adapted from Rick Bayless's Cajeta


  • 1 medium butternut squash, peeled, halved, and seeded (or 1 cup pumpkin puree)
  • 1 1/2 sticks unsalted butter, divided
  • 1 2/3 cup whole wheat pastry flour
  • 2 tsp. baking powder
  • 1 tsp. kosher salt
  • 1/2 tsp. ground cinnamon
  • 1/2 tsp. ground ginger
  • 1/4 tsp. ground nutmeg
  • 1 cup brown sugar
  • 1/2 cup granulated sugar
  • 2 eggs
  • Caramel Filling: 1 cup sugar
  • 1 quart whole milk
  • 1/4 tsp. baking soda, dissolved in 1/2 Tbls. water.
  • 1 Vanilla Bean
  • Ginger Salt and cooked, crumbled bacon for garnish
  • 1 Batch of Maple Brown Butter Icing


  • Preheat your oven to 400 degrees.
  • Slice squash into four equal pieces and place in a baking dish.
  • Top each with a pat of butter and roast in the oven for 35-40 minutes or until very tender.
  • Mash with a potato masher or a fork until squash becomes like a thick puree. Set aside to cool.
  • Reduce oven temperature to 350 degrees.
  • Line muffin tins with paper liners.
  • Melt remaining butter and set aside to cool.
  • In a medium bowl, whisk flour, baking powder, salt, cinnamon, ginger, and nutmeg.
  • In another bowl, whisk sugars, egg, and 1 cup of the cooled squash puree. Slowly whisk in cooled melted butter.
  • Pour squash mixture into flour mixture and fold to combine.
  • Using a cupcake scoop, fill lined muffin cups 3/4 full.
  • Bake for 20-25 minutes or until a tester inserted in the center cake comes out clean.
  • Allow to cool completely before inverting tins.
  • Prepare the caramel filling by first splitting open your vanilla bean lengthwise, scrape out about a 1/4 tsp. and set aside for the icing.
  • Toss the bean along with the sugar and milk into a large heavy bottomed pot.
  • Simmer, stirring constantly, over medium heat until sugar dissolves.
  • Remove from heat and stir in baking soda mixture.
  • Once bubbling subsides, return to heat.
  • Bring to a brisk simmer, but not a boil.
  • Cook, stirring regularly, until milk begins to turn golden. This takes about an hour.
  • Continue stirring and cooking until milk begins to brown, making sure it does not stick to the bottom of the pan.
  • Once a soft ball begins to form, the caramel is ready.
  • Remove from heat and remove vanilla bean.
  • Fill cupcakes by cutting a small inverted cone shape from the top of each. Spoon warm caramel into the hole and sprinkle with ginger salt.
  • Top with Maple Brown Butter Icing and garnish with more ginger salt and bacon.

Categories: Cupcakes  Filling  Sweet 
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