Heat oil in a wide heavy bottomed pan or Dutch oven to 375°F over medium-low heat. Make sure not to use too high a heat! If the heat is too high when you pour in your batter, it will cook too quickly and become very crunchy all the way through. Medium heat allows you to get a crunchy, golden brown outside with a soft, fluffy center!
Mix together the flour, sugar, baking powder, cinnamon, and salt. Set aside.
In a separate bowl, beat together the milk and eggs. Pour this mixture into your flour mixture and combine thoroughly. The batter should be thick but still pourable.
Use a clean squeezable condiment bottle with the spout cut down to create a larger opening or a funnel with a ½ inch opening. Fill your bottle with batter or pour about a cup of batter into your funnel (while holding the funnel closed with a finger).
Hold the bottle or funnel directly over the middle of hot oil. Squeeze the bottle or remove your finger from the hole, and move it in a circular motion, to spiral the dough as it goes into the pan. You want to make a (messy) spiral that is about the size of a small sized plate or a large dinner plate, depending on how big you would like to make them. As you are making your funnel cakes, your batter may thicken as it sits, just add a splash of milk and stir in before refilling your bottle/funnel for the next batch.
Fry until golden brown, flip with tongs, and allow the other side to cook. It should take about 2 minutes per side.
Transfer the funnel cake to paper towels and continue to cook off the batter until you have used it all up..
Serve with powdered sugar or chocolate sauce and berries on top. Best served warm.