Preheat oven to 350 degrees F. Prepare a large cookie sheet with parchment paper.
In a large mixing bowl, mix pumpkin, sugar, oil, milk, and vanilla until well combined.
In another large bowl, combine the flour, baking soda, powder, salt, and pumpkin spice. Add the wet ingredients to the dry ingredients and stir until well combined.
Fold in dark chocolate chips.
Drop the cookie dough by large cookie scoops onto a prepared baking sheet.
Bake for 12-14 minutes or until cookies are just beginning to brown around the edges.
Let the cookies cool on the baking sheet for 5 minutes, then transfer to a wire cooling rack to cool completely.