Heat 4 to 5 inches of vegetable oil in a deep cast iron skillet to 375 degrees.
In a separate dish, mix the 1/4 cup sugar and 1 teaspoon ground cinnamon. Set aside.
In a 3 quart saucepan, add water, brown sugar, salt and butter, heat to a good boil.
Remove from heat and add the flour, stirring in the flour vigorously, mix it in until well blended.
In a separate bowl mix the eggs and vanilla together.
Then add this mixture to the flour mixture.
Stir until well blended and all the egg is completely mixed in.
Fill your decorating tool with the churro dough.
Attach the largest star tip you have, you can also use a decorating bag filled with dough and a large star tip.
Test your oil by placing a small amount of dough in the oil.
The dough should bubble up right away, if it doesn't the oil is not hot enough and you will end up soggy churros.
Once the oil is hot enough, squeeze dough into hot oil about 4 inches long.
Use a knife to release the dough from the decorator tip or use your finger to release the dough but be very, very careful. Cook for 1 minute, turn over with a slotted spoon.
Cook an additional minute or two. (you want a nice golden brown color)
Remove churros with slotted spoon and drain on paper towels.
While still warm, roll each churro into the cinnamon/sugar mixture.