Nutrition per serving may change if servings are adjusted.
2½ cups all-purpose flour
2 tablespoons sugar
1 teaspoon salt
½ cup shortening
¼ cup butter, cut up
½ to ⅔ cup ice water, divided
2 tablespoons seedless raspberry jam
20 paper or wooden lollipop sticks
⅔ cup peach pie filling
¼ teaspoon ground cinnamon
¼ teaspoon almond extract
20 fresh raspberries
Milk for brushing
½ cup powdered sugar
2 teaspoons milk, plus more as needed
⅛ teaspoon almond extract
To prepare pastry: Preheat oven to 400°F. Line two large baking sheets with parchment paper or foil; set aside. In a large bowl, stir together flour, 2 tablespoons sugar and salt. Using a pastry blender, cut in shortening and butter until pieces are pea size.
Sprinkle 1 tablespoon ice water over part of the flour mixture; toss gently with a fork. Push moistened dough to side of bowl. Repeat with additional ice water, 1 tablespoon at a time, until all of the flour mixture is moistened. Gather the dough into a ball and gently knead until it holds together. Divide in half; shape each portion into a ball.
On a lightly floured surface, roll half of the dough at a time into a 12-inch circle. Using a 2½-inch round or scalloped cookie cutter, cut dough into rounds; reroll scraps as necessary (you should have 40 rounds total). Place half of the pastry cutouts 2 inches apart on the prepared baking sheets, allowing space for sticks.
To assemble pops: Spread each round with some of the raspberry jam, leaving a ½ inch border. Press lollipop sticks gently into the pastry cutouts on the baking sheets, positioning a stick about three-fourths of the way over each round.
Place pie filling in a medium bowl. Using kitchen scissors, snip fruit into small pieces. Stir in cinnamon and the ¼ teaspoon almond extract.
Spoon 1 teaspoon of the peach mixture onto the center of each of the pastry cutouts on the baking sheets. Top each with a raspberry. Brush edges with milk. Top with the remaining pastry cutouts; seal edges with a fork. Brush with a little milk.
Bake for 14 to 16 minutes or until golden brown. Using a spatula, transfer pastry pops to wire racks (do not pick up by sticks while hot); cool completely.
To prepare icing: In a small bowl, whisk together powdered sugar, 2 teaspoons milk, and ⅛ teaspoon almond extract. If needed, stir in additional milk, 1 teaspoon at a time, until icing reaches drizzling consistency. Drizzle icing over cooled cookies. If desired, sprinkle evenly with chopped almonds. Let stand until icing is set.
To make ahead: Layer pops between sheets of wax paper in an airtight container; cover. Store at room temperature for up to 2 days.