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 are one of the best desserts – especially when they’re this cute! These Jack O’ Lantern Sandwich Cookies are one of 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 that 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 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 to 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!

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Jack O'Lantern Sandwich Cookies

Ingredients

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

Instructions

  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.





Chocolate Peanut Butter Sandwich (Wedding) Cookies

Chocolate Peanut Butter Sandwich (Wedding) Cookies

A year ago today, I married Bobby. It was truly the best day I could ever have imagined, but the planning was incredibly stressful. I did a lot of the detail work myself – I made the invitations and a lot of the centerpieces, which, looking back, I don’t really recommend. I would have enjoyed the planning process a lot more, if I’d been a little more hands-off. One DIY thing that I highly recommend is doing baked goods for wedding favors. But not just any baked goods: these peanut butter and chocolate sandwich cookies are absolutely perfect in every way. They’re delicious (we got SO many compliments on them), they freeze very well, and they’re that wonderful combination of salty/sweet, chewy/crunchy – and they look super cute in little boxes, tied with ribbon.

I asked my mom to make the favors for my wedding, partially to save money, and partially to send guests home with a favor that they would actually enjoy having. The wedding best favors are edible, tasty, and of course visually pleasing, and you can personalize them with a simple tag or sticker added to the packaging. We decided on peanut butter and chocolate for the cookies, since I chose a white chocolate raspberry wedding cake – something Bobby would have absolutely no interest in eating. And if you read my last post, you know that peanut butter and chocolate is the only flavor combination in the world, according to Bobby. We were inspired by Flourless Peanut Butter Chocolate Ganache Sandwich Cookies from Two Peas & Their Pod, and didn’t do a lot to change the look of the cookie itself, because they really are stunning. But the original version wasn’t exactly what I was looking for flavor-wise, or make-ahead-wise, so we had to do some serious recipe experimentation.

The first task was finding a peanut butter cookie recipe that was stiff enough to sandwich without falling apart, but soft enough to give when bitten into, so the frosting wouldn’t squish out the sides. It also had to freeze well, so it could be made ahead of time – I can’t imagine how we would’ve pulled this off if my mom hadn’t been working on them in the months leading up to the wedding. After rounds of testing, with different brands of peanut butter, flourless vs flour-filled dough, (The version we made is not gluten-free, but the original is, so give it a look if you want something gluten-free) and different levels of sweetness, we settled on our cookie, and got to work creating the fillings. We loved the way Two Peas & Their Pod did it, piling on a sweet creamy peanut butter filling and a rich chocolate ganache, but needed to experiment with them to make sure the flavors went perfectly with our peanut butter cookie. The thing about chocolate and peanut butter is that you have to be very careful with the balance of sweetness/saltiness/bitterness to keep the flavor from being cloying or bland. We used my brothers as taste testers, and had them try so many combinations that they actually started joking about wanting to eat anything but wedding cookies. They’ve gotten over it, I think, because the batch I made for this post got eaten in all of two hours, once I’d finished photographing it.

We put three cookies in each favor box, which meant we had to make about 300 of them – 600 peanut butter cookies to sandwich together. Starting about two months out from the wedding, we made the peanut butter cookies and the fillings in large batches, frosted and sandwiched them,  and then froze them. We weighed the dough and the exact amount of frosting that went on each cookie so they’d be perfectly uniform. They keep so well in the freezer, even with the frosting, that when they defrost they taste and feel like they were baked that morning. They’re little peanut butter and chocolate miracles. We put them in favor boxes the evening before the wedding, straight from the freezer. Since the frosting was rock-solid, they were easy to package neatly, and they defrosted perfectly overnight.

The process of making tons of these cookies wedding-perfect is time-consuming and repetitive and demands attention to detail and lots of freezer space. It would be monumentally more difficult to execute for a very large wedding, especially if you’re not already an experienced baker. That said, these can be made literal months in advance – so you’ll have plenty of time to practice, and the effort yields superbly satisfying results. The recipe I’m posting here is scaled to make about 36 sandwich cookies, as opposed to 300, so the concept is perfect for smaller events as well. If you don’t require perfection and uniformity, you can skip weighing the dough and fillings and the results will still be completely delicious. It’s my plan to make these every October 8th for the rest of my life…and freeze a bunch and save them to eat later in the year, because why not? They will always remind me of the most wonderful evening, being surrounded by my friends and family, wearing my princess dress, and marrying the love of my life. That’s a lot of pressure to put on a cookie, but I there’s no cookie better suited than these.

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Chocolate Peanut Butter Sandwich (Wedding) Cookies

This recipe is heavily adapted from Peanut Butter Chocolate Ganache Sandwich Cookies from Two Peas & Their Pod

Ingredients

Peanut Butter Cookies

  • 2 1/2 cups flour 300g
  • 1 tsp baking powder
  • 1 tsp baking soda
  • 1/4 tsp salt
  • 14 Tbsps butter 198g
  • 1 cup sugar 200g
  • 1 cup brown sugar 215g
  • 1 cup + 2 Tbsps peanut butter 284g
  • 2 eggs

Creamy Peanut Butter Frosting

  • 2 Tbsps peanut butter 32g
  • 1 Tbsp butter, softened
  • 3 Tbsps powdered sugar 25g
  • 2 Tbsp + 1 tsp milk
  • 1 cup powdered sugar 125g

Chocolate Ganache

  • 1/2 cup semi-sweet chocolate chips 85g
  • 1/4 cup heavy cream
  • 4 Tbsps salted butter 56g
  • 6 Tbsps cocoa 30g

Instructions

  1. Make the cookies: stir together flour, baking powder, baking soda, and salt. Set aside. Cream the butter with the two sugars, and then cream in the peanut butter. Stir in the eggs.

    2. Chill the dough at least 4 hours, or overnight. Roll into 18 g balls, and place on baking sheet. Press the balls with the back of a fork to create a criss-cross pattern on the tops. Chill dough balls while preheating oven to 350 degrees (or while previous tray is baking). Bake for 7 minutes, 40 seconds; turn tray, bake for 2 minutes. Cool on wire rack.

    3. Make the peanut butter frosting by adding all of the ingredients to a mixer in the order listed, and beating until well combined and fluffy. 

    4. To make the chocolate ganache, heat the heavy cream in the microwave for 25 seconds. Pour over chocolate chips in a heavy bowl. Let sit 1 minute, then stir until smooth. Melt the butter, stir in the cocoa until smooth. Combine the two chocolates. Allow to cool to room temperature.

    5. To assemble the cookies, place 8g of ganache (roughly 1/2 Tbsp) on one cookie, and 16g of peanut butter frosting on another cookie. Press the two cookies gently together. 

    Cookies will be good in the freezer for up to a year, but will be at their best quality if used within 4 months of freezing.