Position a rack in the center of the oven; preheat to 400 degrees . Line a large baking sheet with parchment. In a bowl, toss the cherries with 1/4 cup sugar; let sit while you make the shortcakes.
In a large bowl, whisk the flour, 1/4 cup sugar, the baking powder and salt. Using your fingertips, work the butter into the flour mixture until it forms fine crumbs (it should look like cornmeal). Make a well in the center of the mixture; pour in 3/4 cup cream. Using a rubber spatula, stir the dough until it just comes together.
Turn out the dough onto a lightly floured work surface. Knead twice, then pat into a 3-by-9-inch-rectangle. Using a thin, sharp knife, cut the dough into 3 squares. Cut each square diagonally into 2 triangles, creating biscuits. Transfer to the prepared baking sheet. Brush the biscuit tops with about 1 tbsp. cream. Bake until golden and springy to the touch, about 15 minutes. Transfer to a rack. Brush with another 1 tbsp. cream; let cool.
Whip the remaining cream with the vanilla and remaining 1 tbsp. sugar until soft peaks form. Split the biscuits horizontally; place the bottoms on plates. Top with the cherries and their juices. Dollop (liberally!) with the whipped cream; cover with the biscuit tops. Serve immediately.
The Quickest Way to Pit Cherries