All My Life's a Cookie Swap: Homemade Chocolate Peppermint Sandwich Cookie

by kellybakes in , ,

peppermint jo jos

The past two weeks have been the most cookie-laden weeks of my life. It all started with the #CookieSwapNYC, an event put on by Maggy Anderson-Keet and Lillian Huang of the amazing group, Bloggers Without Borders. Like most things in the blogging world, I'm a little late to the game, as this was the second annual swap, but my first time going. I'm certainly glad I did! Half of the ticket cost went to benefit WhyHunger, a leading advocate for community-based solutions to problems like poverty and hunger. I was excited to be a part of BWoB to begin with, but partnering with WhyHunger was even more meaningful for me because it was founded by Harry Chapin, who I've been a fan of since I was little. My mom listened to him while I was growing up and always spoke about what a good heart he had and how she admired his commitment to helping others.

Twenty-something years after learning the words to 'All My Life's a Circle,' my life indeed felt pretty circuitous, as I was at Hill Country Barbecue in New York City, with a bunch of good-hearted bloggers, learning about WhyHunger's programs and mission. It was clear both by the number of attendees present and the craftsmanship of the cookies they brought, that everyone in the room was passionate about food!

Maggy introduces WhyHunger

It was wonderful to see old friends, meet new ones and connect face-to-face with folks I had only 'met' on Twitter! [funny how common that's becoming these days, no?] Here's a taste of some of the cookies... [no pun intended, I swear!]

the spread
Gail's gorgeous country Christmas cookies

While I was there, I had the chance to meet the oh-so-sweet Tara of Chip Chip Hooray! This was especially neat because I had been paired with her as part of the Great Food Blogger Cookie Swap, yet another cookie-related blogging event I missed the boat on last year. Unlike CookieSwapNYC, the #fbcookieswap is done through the mail: each blogger gets three names of bloggers who they will mail cookies to at the beginning of December. Then, on Dec. 12th, everyone posts about their experience, including who they mailed cookies to and who they received them from. Normally, they don't get to meet the folks they mail their cookies to (unless they're geographically nearby), but I lucked out! And, as it turns out, she knows my roommate. Small world!

Participating in the #fbcookieswap was a double dose of good, too. In addition to receiving delicious cookies from talented bakers, we also helped raise money for Cookies for Kids' Cancer, national non-profit organization committed to funding new therapies used in the fight against pediatric cancer, which claims the lives of more children in the US than any other disease. Many thanks to Julie of The Little Kitchen and Lindsay of Love and Olive Oil for organizing the entire swap, including making adorable tags & posting packing & shipping tips. **SPOILER ALERT** Lindsay was also one of the bloggers who sent me cookies and her chocolate dipped brownie cookies with rainbow sprinkles were seriously addicting. So much so that I ate four in one sitting. whoopsie.

rainbow sprinkle chocolate brownie cookie from @loveandoliveoil

I also received a box of very festive and very delicious confetti cookies from Kristen of Dine & Dish. [pro tip: If you haven't seen her blog, you should go now. In addition to the delicious recipes, and gorgeous photos, she has one of the prettiest blog layouts I've seen!]

Confetti cookies

For my matches, I wanted to make something sturdy, so my matches wouldn't end up with crumbs. In addition to Tara, I was also sending cookies to Carrie of Bakeaholic Mama and Cayla of Cayla's Cookie Jar, so I wanted to be sure they'd all get their cookies safe and sound. [Instagram let me know that Tara & Carrie got their cookies intact, hopefully Cayla did too!] I decided to adapt a chocolate orange shortbread recipe I made for Valentine's Day to make a homemade version of Trader Joe's Jo Jo's, which are highly addictive chocolate peppermint sandwich cookies and the sole reason I gain 5 lbs each December.

peppermint jo jos 2

And as if that wasn't enough, [phew!] These guys were also entered in the Chocolate Party over at Roxana's Home Baking, where the secret ingredient was, you guessed it, peppermint! If, after making a batch of these, you've still got chocolate and peppermint on the brain, these bloggers have gotcha covered!


Chocolate Peppermint Sandwich Cookies

Recipe Type: dessert, sweets, cookies

Author: kellybakes

Prep time:

1 hour

Cook time:

15 mins

Total time:

1 hour 15 mins


  • For the shortbread
  • 1 stick (1/2 cup) unsalted butter, softened
  • 1/4 cup superfine granulated sugar
  • 1 tsp vanilla extract
  • 1/8 teaspoon salt
  • 3/4 cup all-purpose flour
  • 1/4 cup unsweetened Dutch-process cocoa powder
  • For the filling
  • 1/3 C shortening
  • 1/4 C water
  • 1 1/4 Tbs peppermint extract
  • 1 lb powdered sugar
  • 1/2 tsp salt
  • crushed candy canes, optional


For the shortbread dough

  1. Cream butter, sugar and salt in a bowl until well combined.
  2. Sift flour and cocoa into butter mixture and blend just until mixture forms a soft dough.
  3. Divide dough in half and place each half in between two sheets of parchment paper. Roll the dough out to roughly 1/8″. Chill dough, uncovered, until firm, about 30 minutes.
  4. Preheat oven to 375°F while dough chills.

For the filling

  1. In a stand mixer or bowl, combine shortening, salt, peppermint and water.
  2. Mix on lowest speed with paddle attachment or handbeaters. As liquid gets incorporated into shortening, gradually increase speed until creamy and combined (if you start off at a high speed, you’ll splash water and shortening everywhere–trust me on this one!).
  3. Reduce speed to low and gradually add 1/4 of the powdered sugar until incorporated (if you try to add it all at once, or if the mixer speed is too high, you’ll have powdered sugar all over your kitchen!).
  4. Slowly add the rest of the sugar, working in 4 additions. Taste test. The cream should be spreadable, but not too thin. If the mixture is too thin, you can add more powdered sugar and if it is too stiff, you can add more water.
  5. Remove one sheet of dough from the fridge. Cut circles with a 1" - 1.5" cookie cutter and place on cookie sheet. Bake shortbreads in middle of oven until centers are dry to the touch and edges are slightly darker, about 10-12 minutes. Cool on baking sheet on a rack 10 minutes. Transfer to rack to cool.

Assembling cookies

  1. Once the cookie shells are cool, take one circle, pipe with a piping bag and #7 tip or spread it with a layer of peppermint filling and top with another shortbread circle. Continue assembling cookie sandwiches until you’ve used up all the shells. Roll frosted edges in crushed candy canes, if desired.