Preheat your oven to 350°F (175°C). Line a standard 12-cup muffin tin with festive cupcake liners.
In a medium bowl, whisk together the flour, baking powder, salt, cinnamon, and nutmeg (if using). Set aside.
In a large bowl using a hand mixer or stand mixer fitted with the paddle attachment, beat the softened butter and granulated sugar together on medium-high speed for 2-3 minutes, until light and fluffy.
Add the eggs one at a time, beating well after each addition. Beat in the vanilla extract.
With the mixer on low speed, add the dry flour mixture in three parts, alternating with the milk in two parts, beginning and ending with the flour mixture. Mix just until combined after each addition.
Divide the batter evenly among the prepared cupcake liners, filling each about 2/3 full. Bake for 18-22 minutes, or until a toothpick inserted into the center comes out clean.
While the cupcakes bake, prepare the cinnamon sugar coating. In a small bowl, mix the 1/2 cup sugar and 1 tablespoon cinnamon. In another small bowl, melt the 1/4 cup butter.
Let the cupcakes cool in the pan for 5 minutes, then transfer them to a wire rack. While still warm, gently brush the top of each cupcake with melted butter, then roll or dip the top into the cinnamon-sugar mixture. Let cool completely.
For the frosting, beat the softened cream cheese and butter together on medium speed until completely smooth and creamy, about 2 minutes. Reduce speed to low and gradually add the sifted powdered sugar, cinnamon, and vanilla. Beat until combined. Increase speed to medium-high and beat for 2-3 minutes until fluffy. Add heavy cream 1 tablespoon at a time if needed to reach a pipeable consistency.
Once cupcakes are completely cool, pipe or spread the cinnamon cream cheese frosting onto each one. Garnish with a light sprinkle of the remaining cinnamon sugar, a mini churro piece, or a drizzle of caramel.