Serves 6
¾ cup turbinado sugar, plus more for sprinkling
½ cup light rum
1 tablespoon vanilla extract
½ teaspoon grated orange zest
Kosher salt
3 pounds Bing cherries, pitted and halved
3 tablespoons cornstarch
Cooking spray
6 tablespoons cold unsalted butter, cut into pieces
1½ ounces semisweet chocolate, chopped (about ¼ cup)
All-purpose flour, for dusting
1½ 14-ounce packages refrigerated piecrust dough (3 pieces)
Heavy cream, for brushing
Vanilla ice cream, for serving
Whisk the sugar, rum, vanilla, orange zest and ¼ teaspoon salt in a large bowl until the sugar dissolves. Add the cherries and cornstarch and toss; set aside until juicy, about 30 minutes.
Line a baking sheet with foil and coat with cooking spray. Place six 5-to-6-inch ceramic tart dishes on the prepared pan. Add ¾ cup cherries to each dish using a slotted spoon; top each with 1 tablespoon butter and 2 teaspoons chocolate. Transfer the remaining cherry mixture to a saucepan; add ½ cup water and simmer over medium heat, stirring occasionally, until thickened, 5 to 7 minutes. Divide among the dishes; cool completely.
Dust a surface with flour. Using a paring knife, cut out 6 circles from the piecrust, ½ inch bigger than the tart dishes (use the dishes as a guide). Place on another baking sheet; chill until ready to bake.
Position a rack in the lower third of the oven and preheat to 375˚. Top each dish with a piece of dough, pressing the edge against the dish to seal; pierce several times with a knife. Bake 45 minutes, then brush each pie with heavy cream and sprinkle with sugar. Continue baking until golden, about 15 more minutes. Serve with ice cream.