Mix graham cracker crumbs, brown sugar, and melted butter. Divide between cups (about 2–3 tbsp each) and press down.
Beat cream cheese until smooth. Add pumpkin, brown sugar, pumpkin pie spice, vanilla, and bourbon; mix until creamy.
In another bowl, whip heavy cream to stiff peaks.
Fold whipped cream into pumpkin mixture until smooth.
Spoon or pipe filling into cups over the crust. Chill 3–4 hours or overnight.