It all started with a batch of pumpkin chocolate chip cookies and we still had a bowl of our cinnamon cream cheese frosting sitting in the fridge. The two came together perfectly to form a little magic! Put on a flannel jacket, cozy up in a blanket, and indulge in a cookie destined to be a fall favorite for pumpkin lovers everywhere.

We did something similar once with carrot cake cookies and the result was also magic.

Why Our Recipe

  • All the pumpkin spice and chocolate chip goodness in these classic soft pumpkin cookies.
  • A cinnamon buttercream filling that’ll have you licking your fingers to get every last bit!
A close up view of a pumpkin chocolate chip cookie topped with a cream filling, next to other pumpkin sandwich cookies.

It may seem like a lot at first glance, but I promise it’s okay. All you have to do is whip up a batch of your basic melt-in-your-mouth pumpkin chocolate chip cookies and a quick batch of frosting to go with it. Easy as pumpkin pie. You deserve this.

Ingredient Notes

An overhead view of dry and wet ingredients needed to make pumpkin sandwich cookies.
  • Granulated Sugar: Just your standard white sugar doing its job and keeping things sweet.
  • Salted Butter: We just use salted because it’s convenient. If you’ve only got unsalted, add in an extra pinch of salt. Make sure it’s softened to room temperature.
  • Pumpkin Purée: Be sure to grab pure pumpkin purée, not the stuff meant for pie-filling.
  • Vanilla Extract: Just pour with love.
  • Pumpkin Pie Spice: Or use 1 teaspoon ground cinnamon, 1/2 teaspoon ground nutmeg, 1/2 teaspoon ground cloves, and 1/8 teaspoon ground ginger.
  • Milk Chocolate Chips: If you prefer something less sweet, you can always go for semi-sweet or dark chocolate chips. We’re just team milk chocolate.
  • Powdered Sugar: You’ll want to sift this before mixing it into the frosting unless you’re into the whole “lumpy frosting” vibe (which I’m guessing you’re not).
  • Cream Cheese: Make sure it’s at room temperature. You can use the lower fat if you want. You probably won’t notice a difference.

Evenly Sized Cookies

When it comes to sandwich cookies, it sure helps when all the cookies are the same size so they match up.

A cookie scoop is the easiest way to get evenly sized cookies without guessing. A medium-sized scoop (about 1 1/2 tablespoons) is an excellent choice. Level off the dough with the edge of the bowl to ensure each scoop is the same amount.

Once you’ve ensured it’s the same amount, be sure to roll them nice and round. If they are all roughly the same size and roundness, they’ll spread out uniformly, resulting in cookies that are all the same size.

A close up of a pumpkin chocolate chip cookie sandwich with a cream filling.

Storage & Freezing Instructions

Refrigerate cookies in an airtight container for up to 5 days. The cream cheese frosting needs to stay cold. Let them sit at room temperature for about 10 minutes before eating if you can wait that long.

To freeze, place the sandwiches in a single layer on a baking sheet and freeze for about 1-2 hours until solid. Then, wrap each sandwich individually in plastic wrap and store them in a resealable freezer bag or airtight container. They’ll keep in the freezer for up to 2 months. To thaw, transfer them to the fridge for a few hours or overnight.