3 and 3/4 cups all-purpose flour, plus more for rolling
4 teaspoons baking powder
1 and 1/2 teaspoons salt
1 cup sugar
3/4 cup (1 and 1/2 sticks) very cold unsalted butter
2 cups cold heavy cream, plus more for brushing
2 and 1/2 pounds frozen cherries (or 3 pounds fresh cherries, pitted)
4 teaspoons cornstarch
1 teaspoon pure vanilla extract
Preheat oven to 400 degrees. In a bowl, combine flour, baking powder, salt, and 1/2 cup sugar. Using large holes on a box grater, grate butter into flour mixture. With a fork, stir in cream until dough comes together. On a floured work surface, roll out dough to a 3/4-inch thickness with a floured rolling pin. With a biscuit cutter, cut out rounds of dough. (I used a cookie cutter, and if I had a do-over I would have just used a plain old biscuit cutter so the tips wouldn't all burn.)
In a bowl, combine cherries, 1/2 cup sugar, cornstarch, and vanilla.
Divide mixture among four 1-cup ramekins.
Top each with dough pieces. Brush tops with cream.
Bake cobblers on a rimmed baking sheet until biscuits are golden and juices are bubbling, 40 to 45 minutes, rotating sheet halfway through.
Let cool 15 minutes. Serve warm with vanilla ice cream.