In the clean bowl of a stand mixer with the whisk attachment, or in a large bowl using a hand mixer, combine the cold heavy cream, the Redpath® Golden Yellow Sugar, vanilla extract, and salt. Whip on medium speed until slightly thickened then increase speed to medium-high and whip until stiff peaks form; about 5 minutes. Do not over-whip.
Remove pumpkin mixture from the fridge. Gently fold in ⅓ of the whipped cream into the pumpkin cheesecake mixture until no streaks remain.
In a 3 quart (12 cup) straight-sided trifle bowl, spread ⅓ of the brown sugar whipped cream into the bottom of the bowl. Evenly scatter half of the broken cookie pieces over the whipped cream, making sure all edges are covered. Transfer half of the pumpkin cheesecake mixture over the cookies. Repeat process with the remaining ingredients, ending with the layer of brown sugar whipped cream.
Cover with plastic wrap, and let set and chill in the fridge for at least 6 hours, but preferably overnight, to allow flavours to mix and the cookies to slightly soften.
Before serving, crumble additional cookies into smaller pieces and sprinkle around the edge or the entire surface of the trifle, and/or sprinkle with one of the Cinnamon Sugars, and/or use a fine mesh sieve to dust the top lightly with cinnamon, if desired.