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. Pingback: Flourless Chocolate Pecan Cookies - Around My Family Table

  2. my favorite would have to be chocolate and mint for the holidays… and I do this often with the Enjoy Life cookies – make my own frostings for them! 🙂

  3. Hm… have to say that my favourite traditional holiday cookies are gingersnaps. But I have a new recipe for a chocolate chip cookie with toffee and pretzels that I’m dying to try out! 😀

  4. Stephanie labile on

    I Would love to make these. My daughter would love having the chance to make and eat them, our favorite cookie would have to be our homemade traditional sugar cookies! Yummy

  5. Tough question! When it comes to favorite crowd-pleasing cookie for gift giving, I would have to go with millionaire’s shortbread bars, but for me personally, I would go with peppermint matcha pizzelle cookies. Of course, those preferences tend to change every year!

  6. I only made them once, and my husband keeps asking me to make them again, but we both loved the Carrot Cookie Sandwich cookie that I made. It was so moist and had a cream cheese filling inbetween. I would need to make them gluten free now, so I would have to try and see what I could come up with, but they are sooooo good!! Thank you for the giveaway!! Love these cookies too! <3

  7. I love pumpkin chocolate chip cookies and candy-cane cookies. I think a gingersnap/eggnog sandwich cookie would be amazing!

  8. Pingback: Snickerdoodles {gluten free} | Only Taste Matters

  9. OMG, I want to eat them all! I LOVE Enjoy Life cookies. In fact, I just bought two more boxes today. My son is in a tree nut free classroom and they are perfect for sending him for a snack. My favorite holiday cookie would have to be gingerbread, but snickerdoodles are a close second because we always had them with my Dad’s family at every holiday!

  10. I have been wanting to try these, I will have to get a box soon.
    My favorite cookie recipe is Russian Tea Cakes, also known as Mexican Wedding Cookies. I substitute butter with Earth Balance Spread.

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