Instructions

1. Preheat oven to 350.
2. Prepare and bake the cobbler topping. In a mixing bowl, whisk together the flour, granulated sugar, baking powder, salt and cinnamon. In another mixing bowl, whisk together the egg, milk, melted butter and vanilla. Pour the mixture into the flour mixture and mix until all of the flour mixture is moist. Pour the mixture into a cast iron skillet and bake at 350 for 15-20 minutes. Once done baking, remove from the oven and allow to cool. Then cut into small chunks.
3. Prepare the cobbler filling. In a sauce pan over medium heat, mix together the cherries, cornstarch, bourbon and brown sugar. Cook until the cherries are mashable, about 10-15 minutes, and then mash the cherries. It's ok if you have chunks. You just want to break them up. Once done cooking, set aside and allow to cool.
4. Prepare the ice cream mixture. In the bowl of a stand mixer (or you can use a hand mixer) beat the heavy cream until soft peaks form. Slowly mix in the sweetened condensed milk and vanilla bean until well incorporated.
5. Prepare your Cherry Cobbler Ice Cream. Line a 9x5 loaf pan with parchment paper. Place 1/3 of the cherries in the bottom of the pan. Then top with some of the cobbler topping chunks. Pour enough of the ice cream mixture over top to cover the cherries and cobbler topping chunks. Add another 1/3 of the cherries and cobbler topping mixture. Then pour more ice cream over top, covering the cherries and the chunks. Carefully swirl this layer with a butter knife. Pour enough ice cream to come to just under the rim of the loaf pan. Add the remaining cherries and swirl with a butter knife. Cover with plastic wrap by pressing the plastic wrap onto the surface of the ice cream. Freeze for 6-8 hours or overnight.