Preheat your oven to 350°F (175°C) and line two baking sheets with parchment paper.

In a large mixing bowl, cream together the softened unsalted butter and brown sugar for 2 to 3 minutes until light and fluffy.

Add the maple syrup, large egg, and vanilla extract, and mix until combined, about 1 minute.

In a separate bowl, whisk together the flour, baking soda, salt, and cinnamon, then gradually combine with the wet ingredients on low speed.

Form dough into 1½-inch balls and place them on the prepared baking sheets, flattening each slightly.

Bake for 8 to 10 minutes until edges are golden and centers are soft.

Cool on the baking sheets for 5 minutes, then transfer to a wire rack to cool completely.

Prepare glaze by whisking together powdered sugar, maple syrup, and milk. Drizzle over cooled cookies and let set before serving.