Special equipment: Six 5-inch disposable mini pie plates
For the crust: Put 1 1/2 cups of the flour and the salt in the bowl of a food processor and pulse a few times to combine. Add the shortening and continue to pulse until the dough comes together into small clumps, about the size of a grape. Sprinkle the remaining 1/2 cup flour over the clumps and pulse just until the dry flour is no longer visible, 3 to 5 times. Add 3 tablespoons of the ice water and pulse a few times to moisten the dough. The dough will not come together into a large ball. Squeeze a clump of the dough with your hands. If it is moist and holds together easily, it is ready. If it seems a bit dry still, add an additional tablespoon of water and pulse to blend into the dough. Scrape the dough onto a piece of plastic (it should be in a few large pieces), flatten into a disk and wrap. Chill for at least 1 hour or up to 4 hours to allow the dough to rest.
Divide the dough into 6 even pieces and flatten each piece with your hands. Place a piece into each mini pie plate. Evenly press into the bottom and up the sides of the tin. Fork or crimp the edges, and then place on a rimmed baking sheet. Chill the dough an additional 30 minutes. Preheat the oven to 375 degrees F.
Poke the bottom and sides of the shell with a fork, 6 to 8 times total. Bake the shells until pale golden, about 25 minutes. Cool completely on a wire rack, about 30 minutes.
For the filling: Meanwhile, put the frozen cherries in a strainer set over a bowl to catch the juices as they thaw, 30 to 45 minutes.
When thawed, squeeze the cherries to get more of the juice out of them. Coarsely chop the drained cherries and the maraschino cherries and set aside. Pour the cherry juice into a medium pot and add the maraschino cherry syrup, sugar, cornstarch, salt and 1/2 cup water. Whisk until smooth and then turn the heat to medium. Continue to cook, whisking, until the mixture comes to a boil and thickens slightly, 3 to 5 minutes. Add the chopped cherries and continue to cook until the mixture is very thick and reaches almost a jam consistency, 7 to 9 minutes. Remove from the heat and cool. When the filling is cooled, evenly divide the filling among the pie shells.
For the topping: Combine the heavy cream, sugar and vanilla in a medium bowl and whip, using a whisk, to medium peaks. Spoon a dollop onto each cherry pie or transfer the whipped cream to a piping bag fitted with a star tip and pipe the whipped cream onto each pie.