Preheat oven to 350 F and prepare baking pan with parchment paper. Oil paper a little.
In a a large bowl, beat the butter with a stand mixer for 1 minute. Add brown sugar and beat on low speed until smooth and creamy. Add egg and vanilla extract. Mix in egg and vanilla extract. Beat on medium speed until all ingredients are combined. Mix in pumpkin puree.
In a separate bowl, mix flour, baking soda, cinnamon and pinch of nutmeg.
Add wet ingredients into the dry and mix on low speed until all well combined.
Fold in chocolate chips.
Place about 1 Tbsp. of cookie dough on the baking pan and flatten a little with fork, shape to make a circle.
Bake for 12 - 15 minutes until golden brown. Remove from oven and cool off.