Prepare the Baking Pan: Preheat your oven to 350°F (175°C). Grease a 9x9-inch baking pan with baking spray and line it with parchment paper, leaving some overhang for easy removal.
Mix the Dry Ingredients: In a medium bowl, whisk together the flour, baking soda, cinnamon, and salt. Set aside.
Cream the Butter and Sugar: In a large mixing bowl, beat the softened butter and brown sugar together until light and fluffy—about 2-3 minutes. Scrape down the sides of the bowl as needed.
Add Eggs and Vanilla: Add the eggs one at a time, beating well after each addition. Stir in the vanilla extract.
Combine Wet and Dry Ingredients: Gradually add the dry ingredients to the wet ingredients, mixing until no flour streaks remain. Fold in the oats and raisins until evenly distributed. The dough will be thick and sticky.
Bake the Cookie Bars: Spread the dough evenly into the prepared baking pan. Press it down gently with a spatula. If desired, sprinkle a few extra raisins on top. Bake for 18-20 minutes or until the edges are golden brown. Let the bars cool in the pan for 5-10 minutes before lifting them out using the parchment paper. Transfer to a wire rack to cool completely.
Make the Maple Cinnamon Frosting: While the cookie bars are cooling, beat the softened butter until smooth. Gradually add the powdered sugar, mixing until combined. Stir in the maple syrup, heavy cream, cinnamon, and maple extract (if using) until the frosting is light and fluffy.
Frost and Serve: Spread the frosting evenly over the cooled cookie bars. Cut into squares and serve.