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To make the crust, place flour and 3 tablespoons of the sugar in the bowl of a food processor and pulse to combine. Or, stir together flour and sugar in a medium bowl.
Add butter and pulse in the food processor, or cut butter in using a pastry blender just until mixture resembles coarse crumbs.
Add buttermilk, a couple tablespoons at a time, until dough just comes together (adding 1 to 2 tablespoons more if needed).
Gather up dough, pat into a disc, cover and chill at least 30 minutes.
Preheat the oven to 375°F. Line a large baking sheet with parchment paper. Set aside.
On a lightly floured surface, roll out dough to about 1/8-inch thick.
Cut into 24 (3-inch) circles, rerolling dough as needed.
Place 1/2 cup chopped cherries in a large bowl and mash with a fork or potato masher.
Stir in remaining chopped cherries, 2 tablespoons sugar, tarragon and vanilla and stir until blended. (Do this just before filling the pies; if done too far in advance, the mixture can get too juicy.)
Spoon about 1 tablespoon filling into the center of a circle of dough; brush edges with water.
Top with a second dough circle and crimp edges to seal. Brush top with water and sprinkle with some of the 2 teaspoons sugar. Repeat with remaining ingredients.
Bake on the prepared baking sheet until golden brown, about 30 minutes.