In a large mixing bowl combine sugar, butter, milk and almond extract. Mix until combined. Knead into a large ball.
Roll into 1 in. balls and flatten into a 2 in. circle. Wrap around cherries and tightly roll in hands.
Place covered cherries on waxed lined baking sheet with stems pointing up.
Cover loosely and refrigerate 4 hours or overnight.
Melt the almond bark and shortening in microwave according to package directions.
Holding on to stem, dip cherries into chocolate, set on waxed paper to harden. Store in a covered container.
Refrigerate 1-2 weeks before serving.