Here's what I did - (we didn't carve our pumpkin so here's the steps from the beginning). Cut open the pumpkin and remove all seeds and guts.
Slice pumpkin into several small pieces.
Fill a large pot with hot water and place pumpkin pieces in water. Boil until soft. Let pumpkin cool.
If outer shell of the pumpkin is really tough, you may remove it or you can leave the shell on if you think it will blend well. (*Note: I left the shell on a few pieces and it added nice little darker orange specs to the drink, which I liked).
Place as much of the pumpkin in the blender as possible (you may want to slice into smaller pieces) and blend with part of the water it was boiled in).
Mixture will be thick.
Pour pumpkin mixture back into pot and bring to boil with a cinnamon stick or two. Stir often. Add sugar to taste. Then add milk to thin to your preferred thickness - the drink is meant to be somewhat thick.
Stir until milk/pumpkin have blended and drink has heated through. Add a bit of vanilla 1/2 to 1 tsp. Serve warm.
Annie visited the other night and we enjoyed a delicious cup as we talked. I love this season of warm drinks and being inside talking with friends and family. As we talked and I analyzed how it turned out, I thought it would be pretty to serve with a little whip cream on top with a dash of cinnamon for decoration. If you try this, let me know if you like it.