For the waffles: Whisk together dry ingredients (flour, brown sugar, cinnamon, baking powder, and salt). Add remaining ingredients (egg, milk, vanilla, and butter) and whisk until combined.
For the cinnamon topping: Stir together melted butter, cinnamon, and sugar. Transfer to a piping bag with a small tip cut off, or use a squeeze bottle.
To make the waffles, pour just enough batter to cover the waffle maker. (I used a 3 tablespoon cookie scoop and spread to cover.) Pipe a drizzle of the cinnamon topping over the batter and close the lid. Let waffles cook about 4-6 minutes, or until golden brown. Repeat with remaining batter.
For the cream cheese glaze: Whisk together cream cheese, melted butter, vanilla. powdered sugar, and milk. (I put my cream cheese in the microwave in 5 second intervals until it was soft enough to stir in with the other ingredients.)