Easy Holiday Sandwich Cookies with Fun Homemade Fillings (Mint Chocolate Chip, Raspberry, Lemon and Maple!)

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I love icing, but not fluffy cake. I know, I’m the odd one out, but stick with me here. To fulfill my cravings I frost another delicious dessert, cookies! Recently, I got the wild idea to create some unique frosted fillings for holiday sandwich cookies, and these delicious beauties were born: Mint Chocolate Chip, Lemon-Iced Gingerbread, Berry Sugars, and Maple-Doodles.

Easy Holiday Sandwich Cookies - Mint Chocolate Chip, Lemon-Iced Gingerbread, Berry Sugars, and Maple-Doodle Recipes (all are dairy-free, gluten-free, vegan & top allergen-free!)

I used an assortment of Enjoy Life Cookies in these recipes because a) they come in so many awesome mix & match flavors for making holiday sandwich cookies with both crunchy and soft options; b) they are just so darn good that EVERYONE likes them (and almost everyone can eat them – they’re allergy-friendly); c) they’re dairy-free and gluten-free so both Tony and I get to indulge; and d) they are perfect for joining in the virtual Gluten-Free Cookie Exchange!

18 Gluten-free Cookie Exchange Recipes Including Holiday Sandwich Cookies in Four Fun Flavors: Mint Chocolate Chip, Berry Sugars, Maple-Doodles, and Iced Gingerbread

Check out all 18 recipes in our virtual gluten-free cookie exchange, listed in the order they appear in the photo, left to right, row by row:

Easy Holiday Sandwich Cookies: Mint Chocolate Chip, Lemon-Iced Gingerbread, Berry Sugars, and Maple-Doodle Recipes (all are dairy-free, gluten-free, vegan & top allergen-free!)So which holiday sandwich cookies are my favorites? I have to go with the Mint Chocolate Chip filling with Soft Baked Double Chocolate Brownie Cookies (pictured at the top of this post and in the image below; with crunchy cookies just above – awesome from frozen!) followed by the Berry Creme Filling with Sugar Crisp Hand-Crafted Crunchy Cookies (pictured just above). But I must admit, they’re all pretty darn amazing.

 

Easy Holiday Sandwich Cookies - Mint Chocolate Chip, Lemon-Iced Gingerbread, Berry Sugars, and Maple-Doodle Recipes (all are dairy-free, gluten-free, vegan & top allergen-free!)This post is sponsored by Enjoy Life Foods, but we have been big fans (and consumers) of their cookies for years! 

Special Diet Notes: Holiday Sandwich Cookies with Fun Homemade Cookie Fillings

By ingredients, all of the flavors below are dairy-free / non-dairy, egg-free, gluten-free, nut-free, peanut-free, soy-free, vegan / plant-based, vegetarian, and generally top food allergy-friendly.

Easy Holiday Sandwich Cookies with Fun Homemade Fillings
 
Prep time
Total time
 
Many cookie filling recipes use a liquid to soften them. I stick with a simple shortening / sugar base with no added milk beverage in order to keep the sandwich cookies shelf-stable for the life of the cookies - yes, you can make these ahead. In fact, they taste even better on the second day! Simply store in an airtight container at room temperature to keep the cookies fresh.
Author:
Serves: As many cookies as you like!
Ingredients
Base Filling
  • ¾ cup powdered sugar
  • ¼ cup non-hydrogenated shortening*
  • Pinch salt
Mint Chocolate Chip Filling Add-Ins
Lemon Filling Add-ins
Raspberry Creme Filling Add-Ins
Maple Filling Add-Ins
Instructions
  1. To make the filling, place the powdered sugar, shortening, and salt in a medium bowl and mix until smooth (a hand mixer helps). It will be dry at first, but should come together.
  2. Stir in the add-ins for your desired flavor (using the color ingredients as needed to get the shade you desire). The mixture should be quite thick, like an Oreo icing. But if too thick, you can add a little more shortening - it will still be quite sweet!
Sandwich the Filling ...
  1. Mint Chocolate Chocolate Chip - I use Enjoy Life Soft Baked Double Chocolate Brownie Cookies or Handcrafted Crunchy Double Chocolate Cookies
  2. Lemon-Iced Gingerbread - I use Enjoy Life Soft Baked Gingerbread Spice Cookies
  3. Raspberry Sugars - I use Enjoy Life Handcrafted Crunchy Sugar Crisp Cookies
  4. Maple-Doodles - I use Enjoy Life Soft Baked Snickerdoodles
Notes
*I tested this recipe with both Spectrum Organic Shortening and Nutiva Organic Shortening. We liked the filling texture a touch better with the Spectrum, but used the Nutiva in the Lemon Filling for its natural yellow hue from red palm oil.
**I use a spice grinder to quickly grind the freeze-dried raspberries into a powder. Can't find raspberries? Sub in your favorite freeze-dried berries!
Easy Holiday Sandwich Cookies - Mint Chocolate Chip, Lemon-Iced Gingerbread, Berry Sugars, and Maple-Doodle Recipes (dairy-free, gluten-free, vegan & top allergen-free!)

About Author

Alisa is the founder of GoDairyFree.org, Senior Editor for Allergic Living magazine, and author of the best-selling dairy-free book, Go Dairy Free: The Guide and Cookbook for Milk Allergies, Lactose Intolerance, and Casein-Free Living. Alisa is also a professional recipe creator and product ambassador for the natural food industry.

142 Comments

  1. Those all look really good, especially the mint filling with the brownie cookies! Thanks for the filling recipes, I’ll have to try those 🙂 My favorite sandwich cookie is a classic… Oatmeal cookies with marshmallow creme! My favorite Enjoy Life cookie is the crunchy chocolate chip.

    • I just ate some more of the mint ones (we made A LOT of test batches) and I swear they just get better after a day or two – the flavors really settle.

      Oatmeal w/ marshmallow creme?! That sounds AMAZING! Thanks for sharing that idea Arianna.

  2. Can I pick my favorite filling flavor instead?!? I’m a huge LEMON fan and I think that one would go on just about ANY cookie and make it even better!! (But the maple is sounding pretty awesome too. Hmmmmm……).
    ~jules
    gfJules.com

    • Haha, of course! And I’m trying the lemon with the Sugar Crisps next – it is surprisingly awesome (I didn’t think I would like lemon so much but kept adding more extract!

  3. My favorite holiday cookie is cranberry pistachio biscotti. I know that they are not a traditional holiday cookie but this is the only time of year my mother makes them:-)

  4. Wow, I’m drooling! I love the Enjoy Life cookies, they are the only kind I will buy because they have such quality ingredients and making holiday sandwiches out of them is such a fabulous idea! YUM!

  5. For cookie sandwiches I love pistachio cookies with rose buttercream or the classic oatmeal cookies with vanilla buttercream.

  6. My house loves to do a cookie variety–one chocolatey, one graham/sugar/simple, and one more festive! In the past, for sandwiches, we bought little animal shaped molds and used brownies as the outside, instead of cookies!

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