In a medium bowl, beat heavy cream until it begins to thicken. Add powdered sugar, and beat heavy cream until stiff peaks form. Set aside.

In a large bowl, beat together cream cheese, 1/4 cup sugar, and vanilla until smooth. Add pumpkin puree, cinnamon, nutmeg, ginger, and all spice; beat until smooth. Fold whipped cream into pumpkin mixture until well combined.

Refrigerate about 4 hours, or until cheesecake is firm.

When cheesecake is set, heat 1/2" oil in a large skillet over medium-high heat.

Mix 1/2 cup sugar and 1 tablespoon cinnamon in a bowl, and pour evenly onto a plate. Set aside.

Place about 1/4 cup cheesecake on the lower 1/3 of a tortilla. Fold the bottom edge up away from you and over the filling, then fold in both side edges, and finally roll the burrito away from you until closed.

Fry the burritos in hot oil for 30 to 45 seconds per side, until the tortilla is crispy and golden.

Immediately transfer to a paper towel lined plate, and drain briefly. Roll each chimichanga in the cinnamon-sugar mixture. Place chimichangas on a plate to rest.

Refrigerate chimichangas at least 2 hours (to overnight) to let the filling set up again.

To serve, cut chimichangas in half at an angle with a serrated knife and drizzle with caramel sauce, if desired.