For syrup, heat 1/2 cup cream until just steaming in medium saucepan. Do not boil. Remove from heat and add chocolate; stir until smooth and glossy. Add vanilla. Cool slightly.
For topping, whip cream and sugar with electric mixer in large bowl until soft peaks form.
To assemble: Place one cookie in bottom of treat pop. Add about 1 tablespoon ice cream onto cookie; top with chocolate syrup. Continue layering until treat pop is full. Top with swirl of whipped cream and cherry.