Pour caramel topping on small plate. Dip rim of martini glass in caramel topping; let caramel drip down sides of glass. Set aside.
In cocktail shaker stir together milk, pumpkin, brown sugar and pumpkin pie spice. Cover; shake 30 seconds. Pour into caramel rimmed glass. Top with whipped cream and sprinkle with pumpkin pie spice, if desired.
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