Preheat your waffle iron as per the manufacturer’s instructions.
Whisk together flour, sugar, baking powder, baking soda, salt, and cinnamon in a large bowl. In a separate medium bowl, whisk eggs, buttermilk, oil, and vanilla. Combine the wet and dry ingredients, then gently fold in blueberries.
Grease the waffle iron and pour 1/2 cup of batter onto each side. Close and cook for 2-3 minutes until golden brown. Transfer to a wire rack on a baking sheet.
Mix powdered sugar and milk in a shallow bowl. Dip each waffle into the glaze, allowing it to drip down the sides.
Serve immediately. Store in the refrigerator in an airtight container. To reheat, place on a lightly greased baking sheet in a 350°F oven for 5-7 minutes.