Beat the cream cheese in a medium bowl with an electric mixer on medium speed until smooth. Beat in the sugar & cinnamon. Fold in the whipped cream.
Spoon 1 C cheese mixture into a 4 C trifle bowl. Dip 6 of the cookies, one at a time, into the coffee & place over the cheese layer, overlapping slightly. Spoon 2 Tbsp raspberries over the cookies. Repeat the layers. Spread the remaining cheese mixture over the top. Garnish with the remaining cookies & raspberries. Refrigerate for 1 hour.
Garnish with the chocolate before serving.
Heavy cream will whip faster when the bowl & beaters are cold. Place the bowl & beaters in the freezer for about 15 minutes before using, then use the cream right from the refrigerator.