In bowl, whisk together flour and baking powder. Set aside. In large bowl, with electric hand-mixer, beat butter with sugar until light and fluffy. Beat in egg until blended. Beat in milk and vanilla. Gradually beat in flour mixture -- switching to wooden spoon as required -- until fully incorporated. Shape into 2 disks; wrap each in plastic wrap. Chill at least 1 hr. or overnight.
Preheat oven to 350°F (180°C). Position racks in top and bottom third of oven. On lightly floured surface, roll dough to ¼-in. (5-mm) thickness. Cut out 12 bats with 3.5-in. (9-cm) wide bat-shaped cookie-cutter. Place cut-outs on parchment-lined baking sheet. Re-roll scraps to make 6 more bats. Repeat with remaining disk of dough. Make 36 bat cut-outs total.
Bake, rotating trays once, 10 to 12 min., until cookies are lightly golden around edges. Transfer cookies to wire rack to cool completely.
In microwaveable bowl, melt chocolate in microwave on HIGH, 1 min. at a time, stirring. Cool slightly. Scrape into small re-sealable plastic bag; snip off small corner. Pipe chocolate around edges of each cookie. Pipe 2 dots for bat’s eyes; place silver dragee on each chocolate dot for eyes. Let stand until chocolate sets.
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