In a medium heavy-duty soup pot, heat the olive oil over medium-high heat. Add the chopped shallots and cook until they are starting to caramelize, about 5-6 minutes.
Mash the roasted acorn squash. Add the mashed squash, stock, maple syrup, cinnamon, ½ teaspoon of salt, and ¼ teaspoon of pepper. Bring to a gentle boil, reduce the heat, and simmer for 10 minutes. Remove from the heat and let cool slightly. Puree with an immersion blender.
Adjust the seasoning and serve in shot glasses garnished with a sprinkle of black pepper. If you don’t mind an additional ingredient, I suggest garnishing each glass with a rosemary sprig.