Preheat oven to 375°F.
Prepare baking sheet by lining it with parchment paper and lightly spray the paper with non stick spray.
Unroll one can of the crescent sheets. If using the rolls, pinch the seams together well.
In a small bowl, mix the cream cheese, white sugar, cinnamon and 1 teaspoon of vanilla until well blended and smooth.
Using a spatula, spread half the cream cheese over the crescent sheet. Sprinkle with half of the maraschino cherries (reserve approximately 9 halves to decorate at the end) and half of the nuts.
Roll up crescent sheet starting on the long side. Move the roll to the edge of the parchment paper and repeat the steps with the second crescent sheet.
Move the rolls to the center of the baking sheet and form a circle.
Using a sharp knife cut two-thirds of the way through at one inch intervals all the way around the circle. This should make approximately 13 thin pieces for each half of the roll (26 slices total)
Separate the rolls slightly and twist the rolls sideways to show the filling.
Place in the oven and bake for 20-30 minutes. Cover with aluminum foil if the top is browning too quickly.
Remove the baked crescent ring from the oven and gently slide it on the parchment paper from the baking sheet to a cooling rack to cool.
While it cools combine the powdered sugar and 1 teaspoon of vanilla in a small bowl. Add the milk a little at a time, stirring in between each addition, until you have a thick but pourable icing.
Once cooled completely drizzle with icing and decorate with maraschino cherries on top in groupings of three, like little holly berries.