Preheat oven to 350°F. Prepare Mini Whoopie Pie Pan with vegetable pan spray.
Press cookie dough into prepared pan, filling each cavity 1/2 full.
Bake 10-12 minutes or until cookies are golden brown. Cool in pan 3 minutes. Remove from pan and cool completely on cooling grid.
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. 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 or cookie.