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

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.

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!

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:

• Gluten-free Chocolate Chip Butterscotch Cookies Recipe from Vegetarian Mamma
• Dairy-free Gluten-free Vegan Orange Chocolate Chip Cookies Recipe from Sarah Bakes Gluten Free
• Gluten-free Snickerdoodles Recipe from Only Taste Matters
• Dairy-Free Gluten-free Vegan Ninjabread Men Recipe from Flippin’ Delicious
• Dairy-Free Gluten-free Vanilla Wafers Recipe from gfJules
• Dairy-Free Gluten-free Cranberry Bliss Oatmeal Cookies Recipe from Making It Milk Free
• Dairy-Free Gluten-free Strawberry Thumbprints Recipe from Learning to Eat Allergy-Free
• Dairy-Free Gluten-free Holiday Sandwich Cookie Assortment Recipes from Go Dairy Free
• Gluten-free Cranberry Lime Cornmeal Cookies Recipe from Cafe Johnsonia
• Gluten-free Caramel Hot Chocolate Cookies Recipe from Faithfully Gluten Free
• Dairy-Free Gluten-free No Bake S’mores Cookies Recipe from My Gluten-free Kitchen
• Dairy-free Gluten-Free Sugar Cookies Recipe from Allergy Free Alaska
• Gluten-free Pfeffernusse Recipe from Fearless Dining
• Gluten-free Dark Chocolate Peppermint Cookies Recipe from Maebells
• Dairy-Free Gluten-free Flourless Chocolate Pecan Cookies Recipe from Around My Family Table
• Dairy-Free (option) Gluten-free Chocolate Gingerbread Bars Recipe from Gluten-Free Palate
• Gluten-free Snickerdoodles Recipe from Gluten-Free Homemaker
• Gluten-free Christmas Wreath Cookies Recipe from Gluten-free Frenzy

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.

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

 

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Prep time

15 mins

Total time

15 mins

 

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: Alisa Fleming

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

• ½ teaspoon peppermint extract
• Matcha powder, optional (for color, but tasty too!)
• 2 tablespoons Enjoy Life Mini Chocolate Chips

Lemon Filling Add-ins

• 1 teaspoon lemon extract (or to taste)
• Turmeric, optional (for color)*

Raspberry Creme Filling Add-Ins

• ¼ cup freeze-dried raspberries, ground into a powder**
• ¾ teaspoon pure vanilla flavoring or extract

Maple Filling Add-Ins

• ½ teaspoon maple flavoring

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!

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