In a bowl, break the speculoos cookies (or gingersnaps) into 1-inch pieces or into thirds or quarters. Set aside until needed.
In the bowl of a stand mixer fitted with the paddle attachment, cream the cream cheese on medium speed until smooth and no lumps remain. Scrape down the bowl as necessary.
Add in the pumpkin puree, the Redpath® Golden Yellow Sugar, vanilla extract, cinnamon, ginger, nutmeg, salt, allspice, and cloves. Beat on medium to medium-high speed until mixture is thoroughly combined and free of any lumps.
If using the stand mixer for the brown sugar whipped cream, transfer the pumpkin mixture to another bowl, cover with plastic wrap and place into the fridge.
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.
*Ensure all ingredients for the pumpkin cheesecake filling are at room temperature before proceeding with the recipe.
*If possible, chill the bowl and whisk attachment(s) for at least 10 minutes in the freezer before making the brown sugar whipped cream.
*For an aesthetically pleasing trifle, ensure all layers reach the outer edges of the trifle bowl, so there are no gaps and definite layers can be seen.
*Graham crackers, vanilla wafers, chocolate wafers, or digestive biscuits can be substituted for the speculoos cookies (or gingersnaps).
*If a trifle bowl is not available, use any large bowl or container that can hold 3 quarts (12 cups). Alternatively, make individual servings using Mason jars or drinking glasses.
*For a more pronounced caramel flavour, Redpath® Dark Brown Sugar can be substituted for the Redpath® Golden Yellow Sugar in the pumpkin cheesecake filling and the brown sugar whipped cream. Note that the filling and whipped cream will be darker in colour.