Using a medium bowl, add milk, brown sugar and yeast; stir until well combined. Let sit for 5 minutes.
Using a countertop mixer, add flour, salt, cinnamon, ginger, nutmeg and allspice; mix on low speed until well combined.
Add yeast mixture, pumpkin and melted butter; mix 4-5 minutes on medium speed, or until a smooth dough forms.
Transfer dough into an oiled bowl; cover and let rise in a warm place for 1 hour.
Spray a 9” or 10” cast iron skillet with non-stick baking spray.
Working on a well-floured surface, roll dough into a 16”x12” rectangle.
Using a small bowl, stir together filling ingredients (butter, brown sugar and cinnamon) until well combined. Spread this mixture evenly on top of dough.
Starting with a long edge, roll dough into a tight log. Pinch seams to seal.
Place dough seam-side down and cut into (8) 2” pieces. Place rolls in greased skillet. Cover skillet and let dough rise in a warm spot for 45 minutes.
Preheat oven to 350°F.
Bake rolls for 30-35 minutes, or until tops are golden brown. Let rolls stand for at least 10 minutes before adding glaze.
Using a small bowl, whisk together powdered sugar and milk for the glaze. Drizzle glaze over rolls before serving.