For the filling: Preheat the oven to 400 degrees F. Toss the butternut squash with some olive oil and salt. Place onto a baking sheet and into the oven for 10 to 12 minutes. Remove from the oven and set aside.
Put a saute pan over medium-high heat and melt the butter. Add the apples and salt to taste, and saute until softened. Hit it with the brown sugar and toss until melted. Hit it with the bourbon off the flame, and then carefully tip the pan to the flame to flambe and let the alcohol burn off. Add the apple cider and bring back to a boil. Reduce to a simmer and cook until glazy and delicious, about 10 minutes. Toss in the roasted butternut squash and half of the chopped walnuts.
To assemble: Add about 1/4 cup of the filling into the bottom third of a crepe. Roll the crepe and place seam-side down on a plate. Repeat this process with the remaining ingredients.
To serve: Arrange 1 crepe roll on each serving plate and spoon more butternut squash and apple filling over the top. Garnish with toasted walnuts and serve with Cinnamon Gelato. Dust with powdered sugar.
For the batter: In a mixing bowl, add the flour and salt and make a well in the center. Add the eggs, milk and club soda into the center of the well and whisk together until just combined. The mixture should be like VERY loose pancake batter. If the mixture is a little thick, whisk in a little more milk. Let the batter sit for at least 30 minutes before using. The crepe batter can be made up to 2 days in advance, covered and refrigerated.
For the crepes: Melt about 1/2 teaspoon of the butter in a small nonstick saute pan. The butter should coat the bottom of the pan; if there is a lot of excess, wipe it out with a paper towel. Keep the paper towel handy in case you need it again (you will).
Put the pan over medium heat. Fill a 2-ounce ladle almost to the top with batter and pour it into the preheated pan, tipping and rolling the pan as you ladle the batter to evenly cover the bottom. This will take a little practice; even when you are an experienced crepe maker, the first couple always get wasted. Accept it and move on.
When the edges of the crepe begin to pull away from the edges of the pan and the bottom begins to brown a little, flip the crepe over and cook it for about 1 minute on the other side. Remove the crepe from the pan to a plate and let cool. Stack the crepes as they are cooked between parchment paper squares.
Repeat this process until all the batter is used, wiping the pan with your paper towel or melting a little more butter to the pan as needed.
In a medium saucepan, combine the heavy cream, 1/4 cup of the sugar, the vanilla extract, salt and cinnamon sticks. Bring to a boil, turn off the heat and let sit.
In a small bowl, combine the egg yolks and the remaining 1/4 cup sugar and beat to a homogeneous consistency.
Bring the heavy cream-cinnamon mixture back to a boil and turn the heat off. Whisk a third of the heavy cream mixture into the egg-sugar mixture, and then immediately whisk the egg mixture back into the remaining heavy cream mixture. Bring the mixture back up over medium heat, stirring constantly, until thickened and coats the back of a spoon, about 10 minutes. Strain the mixture and chill over an ice water bath.
Churn the chilled mixture in an ice cream/gelato machine according to the manufacturer's directions.
Use extreme caution when igniting alcohol. Remove the pan from the heat source before adding the alcohol. Pour the alcohol into the pan and carefully ignite with a match or click lighter. Return the pan to the heat and gently swirl to reduce the flames.