Jack O’Lantern Sandwich Cookies

Jack O’Lantern Sandwich Cookies

I didn’t intentionally theme this month based on sandwich cookies, but would that really upset anyone? Sandwich cookies rank with the best desserts – especially when they’re this cute! These Jack O’ Lantern Sandwich Cookies are among my absolute favorite childhood Halloween memories. I grew up helping my mom make them, and to this day I think they’re one of the most delicious treats I know how to make. The cookies are firm without being crunchy, and they have a wonderful sweet, buttery flavor that evokes a cross between a sugar cookie and a perfectly baked shortbread. Filled with a classic vanilla buttercream frosting, they become the kind of sandwich cookie that packaged cookies only dream of being.

The beauty of this recipe is that it doesn’t require any crazy cookie decorating skills. All you have to do is use a great pumpkin cookie cutter (perhaps while you watch The Great Pumpkin), and a paring knife to slice little triangles in the dough for the eyes and noses of your jack o’ lanterns. A yellow buttercream goes between the cookies, so it looks like the jack o’ lantern has a lit candle inside – no extra skill work required. I like these cookies sans mouths because I think they’re elegant in their simplicity, while still looking fun, and most importantly, delicious. Halloween baking always has the potential to go to a very goofy, over-the-top place, where treats look festive, but not necessarily appetizing. It’s one of my baking mantras to never sacrifice how mouth-wateringly edible something looks in the name of making it look cute.

There are a few things you should know before you make these cookies. The first is that the dough does require time to chill, so plan accordingly. The dough itself comes together in all of about five minutes, so you can make a batch now and be ready to cut and bake it tonight. The second is that these cookies are fairly fragile, so one or two will break no matter what you do. You’ll want to eat these broken ones immediately, which is fine, since broken cookies have no calories. It’s a well-known scientific fact. That said, as long as you handle them gently, and frost them with the cookie laying on a flat surface, too much breakage won’t be an issue. You can also roll your dough out slightly thicker than the 1/8 of an inch that I usually go for, to yield sturdier cookies.


Halloween theme aside, this cookie recipe is like the holy grail of roll-and-cut cookie recipes: easy to whip up, buttery without being too soft, crisp without being crunchy, and perfect for all forms of cookie decorating because it’s endlessly versatile. You can use food coloring to make the dough and frosting any color of the rainbow, and cut it into just about any shape you desire. I use this recipe to make Christmas cookies, and heart-shaped cookies for Valentine’s day. You can also substitute any flavor frosting or even a chocolate ganache for the filling, or just bake the cookies a little thicker and top them with frosting and sprinkles – no sandwiching required. Jack O’ Lanterns are easily my favorite way to use this recipe because Halloween is the best, but I won’t blame you if you find yourself loving this recipe for beautiful frosted Christmas cookies instead!


Jack O'Lantern Sandwich Cookies


Jack O' Lantern Sugar Cookies

  • 3/4 cup butter, softened
  • 1/4 cup sugar
  • 1/4 cup brown sugar
  • 1 egg yolk
  • 12 drops yellow food coloring
  • 4 drops red food coloring
  • 1 3/4 cups flour
  • 1/8 tsp salt
  • 3/4 tsp baking powder

Vanilla Frosting

  • 1/2 cup butter
  • 1 1/2 cups powdered sugar, divided use
  • 1 Tbsp milk
  • 2 dashes salt
  • 10 drops yellow food coloring
  • 1/4 tsp vanilla


  1. Make the cookie dough: cream together butter and sugars. Beat in the yolk, and red and yellow food colorings.

    2. Stir remaining ingredients together, and add to butter mixture. Mix well. Chill for 4 hours or overnight.

    3. Roll dough to 1/8" - 1/4” thickness, and cut into pumpkin shapes with a cookie cutter. Using a small, sharp knife, cut triangle eyes and noses on half of the pumpkins. You can also draw curved lines with the tip of a knife on the surface of the cookies, to mimic the ridges on a real pumpkin - just be careful not to cut all the way through the cookie.

    4. Bake at 350° F for 8 - 10 minutes, or until the edges are just barely, or just about to, brown. Cool completely on a wire rack.

    5. To make the frosting, cream together butter and 1 cup of the powdered sugar. Stir in vanilla, salt, and milk. Stir in remaining powdered sugar. When sugar is completely incorporated, add food coloring and stir until frosting is uniform. Optional: Whip in a stand mixer on high speed, to yield more fluffy, voluminous frosting.

    5. When completely cool, spread the non-face pumpkins with the icing, and top with the pumpkins with faces. DO NOT try to press the top cookies down to make the icing squeeze up through the cut-outs - it will just break the cookies.