Add crushed graham crackers to a small plate. Add either store-bought or homemade caramel to another shallow plate, ensuring it is relatively thin. Dip the rim of a martini or coupe glass first into the caramel and then into the crushed graham cracker until the rim is evenly coated. Set glasses aside and discard remaining graham crackers and caramel.
1 graham cracker, ⅛ cup caramel
Add heavy cream, powdered sugar, and vanilla extract to the bowl of a stand mixer fitted with a whisk attachment or to a medium bowl if using a hand mixer. Beat on medium-high speed for 2-3 minutes until soft peaks form but whipped cream is slightly less whipped than usual.
½ cup heavy cream, 1 tablespoon powdered sugar, ¼ teaspoon vanilla extract
Fill a cocktail shaker with ice cubes and add pumpkin puree, Baileys, vodka, and pumpkin pie spice. Shake well for at least 20 seconds, then immediately strain into prepared glasses.
2 tablespoons pumpkin puree, 2 ounces Baileys, 4 ounces vodka, ¼ teaspoon pumpkin pie spice
Top with whipped cream and sprinkle with additional pumpkin pie spice.