Make and blind bake your pie crust, then cool completely.

Add the maple syrup, half-and-half, eggs, brown sugar, cornstarch, and salt to a medium saucepan and whisk together until completely combined. Heat over medium-low heat and whisk, almost continuously, until the custard is thick like pudding. This step may take 20 minutes (or even longer depending on your stovetop).

When the custard is thick, remove from the heat and whisk in the vanilla and butter. Continue whisking until the butter is melted.

Transfer the pudding to the cooled pie shell and place a piece of plastic wrap or wax paper directly on top of the custard to prevent a skin from forming, but do not cover the crust. Refrigerate 6 hours or overnight.

To make the whipped cream, use a handheld mixer to whip the heavy cream, bourbon, vanilla extract, and powdered sugar together. Evenly spread the whipped cream over the maple pudding. After topping with the whipped cream, refrigerate at least 30 minutes before serving or up to 2 hours.

Leftover pie must be refrigerated and is best within 3 days.