Cut a half-inch round slice from the center of the watermelon, rind on, for Jack's face. Set aside.
Peel remaining watermelon and use a heart cookie cutter to cut pieces. Halve each heart vertically into ghost shapes. Punch eye and mouth holes with a drinking straw. Pat dry.
Place the round watermelon slice on your board. Sketch Jack's features lightly with a toothpick, then carve out the eyes with a paring knife, punch nose holes with a straw, and cut the jagged smile. Blot with a paper towel.
Thread grapes and blackberries onto mini skewers, alternating fruit as you go.
Slice kiwi into rounds and orange into rounds or half-moons. Arrange along the outer edge of the board.
Place watermelon ghosts and berry skewers around Jack. Fill gaps with cherries and loose grapes.
Tuck in fresh mint sprigs and drizzle with balsamic reduction just before serving if desired.