Gather all ingredients.

Beat cream in a chilled glass or metal bowl with an electric mixer. Gradually add confectioners' sugar and vanilla extract, continuing to beat until stiff peaks form.

Spread a generous teaspoon of whipped cream onto each cookie.

Press cookies together to make 3-inch stacks.

Spread whipped cream in a 1-inch-wide line down the center of a serving platter. Turn cookie stacks sideways and join into a log; place in the whipped cream to secure.

Frost cookie log with remaining whipped cream and sprinkle with grated chocolate. Cover tightly and refrigerate, 8 hours to overnight.

To serve, slice diagonally to create striped pieces.