Preheat oven to 375 degrees.

In a mixing bowl cream mix together cream cheese, sugar, flour and vanilla until combined. Set aside.

In a different mixing bowl mix together pumpkin and pumpkin pie spice.

Unroll crescent roll dough leaving it in one big rectangle and press together seams. Lay the crescent roll dough on an ungreased half sheet baking pan. Cut 1/2 inch strips on each side of crescent roll dough rectangle leaving a 3-4 inch center piece that is not cut. Carefully spread the cream cheese mixture down the center of dough. Top with pumpkin mixture.

Fold cut pieces of crescent dough forming a braid. Some of the filling will be visible. Tuck the end over and into the braid.

Bake for 15-20 minutes or until crescent dough is golden brown. Cool 5 minutes. Remove to serving platter.

In a small mixing bowl combine cinnamon, powdered sugar and milk. Drizzle over crescent braid.