In a small bowl, combine the sugar, butter, milk and extract. Knead until smooth and pliable. Shape into 1-in. balls and flatten each into a 2-in. circle.

Wrap one circle around each cherry and lightly roll in hands. Place with stems up on waxed paper-lined baking sheet. Cover loosely and refrigerate 4 hours or overnight.

In a microwave, melt chocolate and shortening; stir until smooth. Holding on to the stems, dip cherries into chocolate; allow excess to drip off. Place on waxed paper until set. Store in a covered container. Refrigerate 1-2 weeks before serving.