Combine all filling ingredients except bourbon in saucepan. Cook over medium-low heat 2-4 minutes or until bubbly and thickened.
Remove from heat; stir in 1 tablespoon bourbon. Refrigerate until completely chilled.
Place flour into food processor bowl fitted with metal blade. Add butter; pulse until mixture resembles coarse crumbs.
Add 1 egg and 1 tablespoon water at a time, pulsing between each addition, just until dough forms.
Shape dough into disk; flatten slightly. Wrap in plastic food wrap; refrigerate 1 hour or until firm.
Line baking sheet with parchment paper; set aside. Place 1 egg and 1 teaspoon water into bowl; beat with whisk. Set aside.
Roll out dough on lightly floured surface to 15-inch square about 1/8-inch thickness.
Cut dough in half horizontally, then cut dough vertically at 5-inch mark and 10-inch mark, forming 6 (7 1/2×5-inch) rectangles; brush edges with egg wash.
Divide filling evenly among rectangles, mounding on one side of each rectangle, leaving 1-inch border around edge.
Fold remaining dough over filling; crimp edges using fork.
Place onto prepared baking sheet; brush tops with egg wash. Refrigerate at least 10 minutes.
Heat oven to 375°F.
Combine 1/2 cup powdered sugar and 1 teaspoon bourbon in bowl. Add enough half & half for desired glazing consistency. Set aside.
Bake pies 18-20 minutes or until golden brown. Immediately spread glaze over top of pies.