Poke a few holes in the sweet potatoes and bake for 1 hour or until soft and tender. When the sweet potatoes are cooked, slice them in half and allow to cool.
Meanwhile, add the maple syrup and cinnamon to a large soup pot, bring to a boil and then reduce the heat to a simmer, simmer for 10-15 minutes or until the maple has thickened and reduced to a syrup. Be careful not to let it get too thick, you just want it to thicken to a honey consistency.
Once the sweet potatoes are cool enough to handle, peel away the skins and add the orange flesh to the bowl of a food processor or high powered blender. Add 1 cup of broth and puree until smooth. Slowly stir the sweet potato mixture into the thickened maple syrup. Add the remaining 1 1/2 cups broth, the apple cider, thyme, nutmeg, cayenne and a pinch of salt + pepper. Cook over medium heat until warmed through, about 10 minutes. Stir in the bourbon (if using) and cream. Continue to cook another 5 minutes minutes and then add the cheese + butter, cook until the cheese is melted and the soup is silky smooth. If the soup seems too thick, add more broth to thin. Keep over low heat until ready to serve.
Cheddar Cinnamon Sugar Twist
Heat oven to 350 degrees F. Line two baking sheets with parchment paper.
Add sugar and cinnamon to small bowl and mix to combine.
Open one sheet of puff pastry on cutting board. Brush surface lightly with the melted butter. Sprinkle surface generously with cinnamon sugar, leaving some for sprinkling on just before baking.
Sprinkle with 1/2 cup cheese to evenly cover entire surface. Use your hands and press cheese into puff pastry to adhere. Cut puff pastry into long 1/2-inch-wide strips. Gently twist each strip several times. Repeat with remaining puff pastry strips until everything has been used. Place finished twists on prepared baking sheets. Brush twist with melted butter and sprinkle generously with cinnamon sugar. Bake 12-15 minutes or until puff pastry is golden. Be careful not to over bake. Serve with the warm soup.
*The soup can be made up to two days in advance and stored in the fridge. Simmer over low heat until warmed through to serve.