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Preheat your oven to 350°F (175°C) and line two baking sheets with parchment paper.
In a medium bowl, whisk together the flour, baking soda, baking powder, salt, and cinnamon. Set aside.
In a large bowl, beat the softened butter, brown sugar, and granulated sugar together until light and fluffy. Add the egg, maple syrup, and vanilla extract, and beat until well combined.
Gradually add the dry ingredients to the wet ingredients, alternating with the buttermilk. Mix until just combined.
Drop rounded tablespoons of dough onto the prepared baking sheets, spacing them about 2 inches apart. Bake for 10-12 minutes, or until the edges are lightly golden and the centers are set. Let the cookies cool completely on a wire rack.
In a medium bowl, beat the softened cream cheese and butter until smooth. Gradually add the powdered sugar, maple syrup, and vanilla extract, beating until the filling is creamy and smooth.
Once the cookies are completely cooled, spread or pipe a generous amount of maple filling onto the flat side of half of the cookies. Top with the remaining cookies to create whoopie pie sandwiches.