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In a large bowl add the peaches, bourbon, 1/4 cup sugar, cornstarch, and cinnamon and mix well to coat the peaches evenly; set aside.
Prepare the dumplings: Into food processor add the flour, 1/2 cup sugar, baking powder, and salt. Cut 12 tablespoons (1 1/2 sticks) butter into small pieces. Add it to the flour mixture and pulse until the mixture looks like wet sand. Mix just until the dough comes together. Don't overwork; the dough should be slightly sticky but manageable.
In a 10-inch cast iron skillet over medium-low heat, melt the remaining 2 tablespoons butter. Add the peaches and cook gently until heated through, about 5 minutes. Drop the dough by tablespoons over the warm peaches. There can be gaps; the dough will puff up and spread out as it bakes. Brush the top with some heavy cream and sprinkle with some sugar, put it into the oven on a baking sheet to catch any drips. Cook for 40 to 45 minutes until the top is browned and the fruit is bubbling.