Put the cold water in a wide, shallow bowl and sprinkle the gelatin over it. Set aside for 8 minutes to let the gelatin to soften and absorb the water.
In a blender, combine heavy cream, buttermilk, maple syrup, pumpkin pie spice, vanilla and squash puree. Lightly blend just so that it combines and is smooth. Pour into a medium sized saucepan and stir in softened gelatin. Gently bring to medium heat, so the steam rolls off of it, but it does NOT boil, and whisking so that the gelatin dissolves. Cook at this temperature for 3 minutes, then remove from heat and strain through a colander into a liquid measuring cup.
Then pour and divide the mixture among 6 ounce, or 4 ounce ramekins/pots/bowls. Let pots cool to room temperature, then cover and refrigerate for at least 4 hours, up to 3 days.
When ready to serve, top with crushed cinnamon cookies and swirl of maple syrup. If you’ve reserved some of the squash, you can add that to the top as well.