Prepare the Wreath Base

1. Crush the Graham Crackers: In a food processor or using a plastic bag and rolling pin, crush the graham crackers until they form fine crumbs.
2. Mix the Base: In a large bowl, combine the graham cracker crumbs, cocoa powder, powdered sugar, melted butter, milk, and vanilla extract. Mix until the crumbs are well-coated and the mixture sticks together when pressed.
3. Shape the Wreath: Transfer the mixture to a parchment-lined baking sheet. Press it into a circle, forming a wreath shape. Use your hands or the back of a spoon to smooth the edges and create a solid base. Chill in the fridge for at least 30 minutes to firm up.

Make the Whipped Cream Filling

1. Whip the Cream: In a large mixing bowl, beat the heavy whipping cream, powdered sugar, and vanilla extract with an electric mixer until stiff peaks form.
2. Fold in Cherries: Gently fold in the chopped maraschino cherries into the whipped cream mixture, ensuring an even distribution.

Assemble the Wreath

1. Fill the Wreath: Carefully spread the whipped cream and cherry mixture on top of the graham cracker wreath base. Use a spatula to spread it evenly and smooth the top.
2. Chill Again: Return the wreath to the fridge for an additional 30 minutes to set.

Finish with Chocolate Drizzle

1. Drizzle the Chocolate: Melt the chocolate chips in the microwave in 20-second intervals, stirring in between, until smooth. Drizzle the melted chocolate over the whipped cream and cherry filling for a glossy finish.
2. Garnish: If desired, top with additional maraschino cherries or chocolate shavings for extra flair.

Serve and Enjoy

1. Serve: Slice the wreath into wedges and serve chilled. This dessert pairs wonderfully with a hot cup of cocoa or festive holiday drinks.