Preheat the oven to 375℉. Line cupcake pan(s) with paper cups. Set aside.
In a large bowl, whisk together the oil, sugar, and vanilla. Add the pumpkin, eggs, and milk. Whisk until well-combined.
In a separate bowl, stir together the flour, baking soda, baking powder, salt and pumpkin pie spice. Add the dry ingredients to the wet mixture. Stir until just combined.
Fill prepared cupcake wells each 3/4 full; to make 16 cupcakes. Bake at 375˚F for 18-20 minutes or until a toothpick inserted in the center comes out with just a few moist crumbs. Do not over-bake. Cool completely.
CREAM CHEESE FROSTING: Place the cream cheese in a large mixing bowl. Beat until smooth with an electric hand mixer. Gradually add the butter 2 Tablespoons at a time, and continue beating until smooth and well blended. Add powdered sugar and vanilla all at once. Blend until combined and smooth.
Add frosting to a piping bag fitted with a tip (I used a Wilton 1M) and swirl on top of cupcakes. Should be just enough for 16 cupcakes if piped as pictured. If the frosting gets too soft, throw it in the fridge for 15 minutes to firm it up, as needed.
Notes
Spices: Use 2 ½ tsp ground cinnamon, ¾ tsp ground ginger, ¼ tsp ground nutmeg, ¼ tsp ground cloves, and ¼ tsp ground allspice in place of pumpkin pie spice.
STORAGE INSTRUCTIONS
Room Temperature:Unfrosted cupcakes can sit at room temperature in an airtight container for up to 3 days.
Refrigerator:Frosted cupcakes should be stored in an airtight container in the fridge for up to 5 days. Let them sit out for about 20 minutes before serving for the best texture. Unfrosted cupcakes can last up to 1 week in the fridge.
Freezer: You can freeze unfrosted or frosted cupcakes for up to 3 months if individually wrapped in plastic wrap and stored in a freezer-safe bag or container. Be sure to flash freeze frosted cupcakes for 1 hour, or until the frosting is frozen solid, before wrapping and freezing.