Preheat oven to 350° Fahrenheit.
Add 2 pounds pitted cherries, ⅔ cup granulated sugar, 2 tablespoons fresh lemon juice, and 3 tablespoons cornstarch to medium saucepan. Place saucepan on stovetop over medium heat.
Simmer filling ingredients, stirring frequently, approximately 5 to 10 minutes or until cherries have burst and mixture has thickened. Once thickened, remove saucepan from heat and set aside.
Place 5 tablespoons unsalted butter in baking dish, then place baking dish in preheated oven. Bake butter 3 to 5 minutes or until butter is completely melted.
While butter melts, add 1 cup all-purpose flour, 1 cup granulated sugar, 1 cup whole milk, and 1 teaspoon fresh baking powder to mixing bowl. Mix ingredients together until incorporated into wet batter with no lumps of dry ingredients remaining.
Carefully remove baking dish from oven. Pour prepared batter into baking dish, covering melted butter completely. Do not stir batter and butter together.
Pour prepared cherry filling evenly over layer of batter. Filling may settle into batter slightly - do not stir filling and batter together.
Return baking dish to oven. Bake cobbler 45 minutes or until filling is bubbly and crust is baked through and golden brown.
Carefully remove baking dish from oven and set aside. Allow cobbler to cool 10 minutes.
After 10 minutes, serve cobbler warm with vanilla bean ice cream if desired.