Pour enough oil into a large skillet so it's about 1 inch deep. Heat the oil over medium-high heat until a deep-fry thermometer registers between 280 to 300 degrees F.
Meanwhile, whisk together the flour, granulated sugar, baking powder, cinnamon and salt in a large bowl. Make a well in the center and add the milk, egg and 1 tablespoon of the maple syrup. Whisk the dry and wet ingredients together until smooth.
Transfer the batter to a large pastry bag fitted with a #3 or 4 open tip. Working in batches and making a few at a time, carefully squeeze the batter into the oil in a circular pattern and then back and forth, to make a free-form spider web-like design, 3 to 4 inches in diameter. Cook until the bottoms are golden, about 2 minutes. Using tongs or a slotted spoon, turn the fritters over and cook until golden on the other side, about 1 minute more. Transfer the fritters to paper towels to drain briefly. Repeat with the remaining batter.
Brush the webs lightly with maple syrup and dust with confectioners' sugar. Serve warm or at room temperature garnished with jelly spiders or nonpareils if using.
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