Step 1: Puree watermelon and sugar in batches in your blender or food processor until smooth and strain into a medium bowl. Cover and freeze until puree is slightly slushy, but not quite solid, about 2 to 3 hours. Remove from freezer, stir well and add in chocolate chips.
Step 2: Place twelve 5-ounce disposable cups in a shallow baking pan and spoon watermelon puree into cups, leaving about a 1/2 inch left from the rim. Place pan in freezer for 2 hours, or until puree is solid, but not rock hard.
Step 3: Allow lime sherbet to soften a bit, then spread over top of each portion of watermelon puree so that it comes up to the edge of the cup.
Step 4: Smooth sherbet with the back of a spoon and cover each cup with plastic wrap. Cut a small slit in the center of each cup and insert a popsicle stick into each pop so that it almost reaches the bottom of the cups.
Step 5: Freeze until solid (about 6-8 hours or overnight).
Step 6: Allow pops to sit at room temperature for about a minute, then gently pull out from the cups -- enjoy!
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