Prepare the vanilla pudding mix according to the package instructions. Transfer to a bowl and stir in the brown sugar and pumpkin pie mix. Cover and refrigerate for 30 minutes.
Break the pumpkin chocolate chip cookies into 3/4-inch pieces. Layer the bottom of the glasses or trifle bowl with ingredients in the following order: cookies, pudding mixture, whipped topping. Repeat layers.
Cover and refrigerate for at least 4 hours (this dessert can be refrigerated overnight). Top with caramel topping before serving.
Note: You can substitute Cheryl's Pecan Pie Bars for the pumpkin chocolate chip cookies for an even more decadent Thanksgiving dessert!