This pie is best when made ahead and baked straight from the freezer. Leftovers—should there be any—are great for breakfast.
Ingredients
For the filling
1/2 cup granulated sugar
1 cup (about 5 oz.) dried tart cherries
2 lb. (about 4 large) firm, tart apples (such as Braeburn, Jonagold, or Pink Lady)
1 lb. (about 3 medium) firm-ripe pears (such as Anjou)
3 Tbs. all-purpose flour
1/2 tsp. ground cinnamon
1/4 tsp. ground nutmeg
Pinch kosher salt
For the dough
9 oz. (2 cups) unbleached all-purpose flour
2 Tbs. granulated sugar
1/4 tsp. table salt or 1/2 tsp. kosher salt
8 oz. (1 cup) very cold unsalted butter, cut into 1/2-inch cubes
2 Tbs. to 1/4 cup ice-cold water
For baking
1 egg yolk, beaten
2 Tbs. heavy cream or milk
Preparation
Make the filling
In a small saucepan, combine 1/4 cup of the sugar with 1/2 cup water; bring to a boil. Add the dried cherries and simmer for 3 minutes. Set aside to cool to room temperature. Drain. (Save the liquid to drizzle on ice cream.) Peel, core, and cut the apples and pears into 1/3-inch-thick slices. In a large bowl, toss the apples, pears, and cherries with the remaining 1/4 cup sugar, flour, cinnamon, nutmeg, and salt. Set aside.
Make the dough
Put the flour, sugar, and salt in the bowl of a stand mixer fitted with the paddle attachment (or in a large bowl, if mixing by hand). Mix for a second or two to blend. Add the butter, and with the mixer on low or by hand with a pastry cutter, work the mixture until it’s crumbly and the largest pieces of butter are no bigger than a pea, about 2 minutes. Test the butter to make sure it is still cold enough by collecting a small amount and molding it into a small cube. If after handling it your fingers are greasy, refrigerate the mixture for 15 minutes before proceeding. With the mixer still on low (or tossing with a fork if mixing by hand), sprinkle 2 Tbs. of the cold water evenly over the flour and butter. Work the dough until it just pulls together in a shaggy mass, adding more water, if needed, 1 tsp. at a time. Divide the dough in half and pat each piece into a disk; refrigerate one piece.
Assemble and freeze the pie
On a floured work surface, roll the other piece of dough into a 12-inch circle, turning the dough and reflouring as necessary to prevent sticking. Transfer the dough to a 9-inch pie plate, fitting it into the plate without stretching. Trim so that there is 1 inch of dough hanging over the edge of the plate.
Pour the filling into the pie shell and press down with your palms to arrange it evenly. (This will keep the apples from poking holes in the top crust.) Refrigerate while you roll out the other half of the dough.
Roll out the other piece of dough the same way as the first half. Drape it over the pie and trim the edge of the top crust to the same size as the bottom. Roll the edges together and under so they rest on the rim of the pie plate and form a tall edge. Crimp the edge, making sure the crusts are sealed. Vent the top by poking the tip of a paring knife through it in a few places.
Wrap the pie in plastic wrap and freeze for at least 1 day.
Bake the pie
Position a rack at the bottom of the oven. Line a rimmed baking sheet with foil and set it on the rack. Heat the oven to 350°F.
In a small bowl, whisk the egg yolk with the milk or cream. Brush the top of the pie with the egg wash (you won’t need it all). The egg wash may freeze as you are applying it; re-pierce the steam vents if they become clogged. Bake on the heated baking sheet until the crust is deep golden and the juices are bubbling, about 1 hour, 45 minutes. If the edges start to get too dark, loosely drape foil around the sides or cover the edges with a pie guard.
Cool on a rack to room temperature, about 4 hours, before serving.
Make Ahead Tips
You can assemble the pie up to 6 weeks ahead. Freeze the pie wrapped in foil, and it’s ready to bake.