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.
- ¾ cup powdered sugar
- ¼ cup non-hydrogenated shortening*
- Pinch salt
- ½ teaspoon peppermint extract
- Matcha powder, optional (for color, but tasty too!)
- 2 tablespoons Enjoy Life Mini Chocolate Chips
- 1 teaspoon lemon extract (or to taste)
- Turmeric, optional (for color)*
- ¼ cup freeze-dried raspberries, ground into a powder**
- ¾ teaspoon pure vanilla flavoring or extract
- ½ teaspoon maple flavoring
- 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.
- 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!
- Mint Chocolate Chocolate Chip - I use Enjoy Life Soft Baked Double Chocolate Brownie Cookies or Handcrafted Crunchy Double Chocolate Cookies
- Lemon-Iced Gingerbread - I use Enjoy Life Soft Baked Gingerbread Spice Cookies
- Raspberry Sugars - I use Enjoy Life Handcrafted Crunchy Sugar Crisp Cookies
- Maple-Doodles - I use Enjoy Life Soft Baked Snickerdoodles
**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!
146 Comments
I don’t care what time of year it is–soft chocolate chip or peanut butter win my vegan heart.
The classics can’t ever be beat, I agree Abby.
Such beautiful cookies!!
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At holiday time I really like gingerbread cookies. Maybe a caramel flavor filled filling or peanut butter filling.
Hmm, caramel sounds tricky but doable! And I think I might make a PB one today!
hmmmmm….I think it’s a tie between almond crescent cookies and frosted sugar cookies. both a holiday must-bake!
I would have taken you for a crispy cookie gal Sarah 🙂
My kids love cut-out sugar cookies. I’m more of a dairy free ice cream gal myself. 😉
I’m with you – ice cream first, crumbled cookies (or cookie dough) on top!
I love holiday sugar cookies
I’m betting the gingerbread spice is also quite good with a lavender filling. I made ice cream sandwiches this summer with ginger snaps and lavender ice cream that were out of this world!
Mmm, indeed, that would be so unique and fragrant.
My favorite holiday cookie is the chocolate crinkles.
Sugar cookies rock but i now eat pumpkin or snicker doodle type! I think a vanilla cream center would be lovely or chai spice. Another creative combination would be chocolate cookies with coconut cream center. Thank you.
Ooh, chai spice! I love that idea. And coconut cream would be decadent, too. Great suggestions Jackie!
My family loves peanut butter cookies all year long! Now I make them gluten free and dairy free since both of my kids have been diagnosed with food allergies and we are still able to enjoy them!
The mentioned chocolate chip butterscotch cookies make me remember an old recipe I used to be asked to make all the time, I can’t wait to try that one DGF! 🙂
My favorite holiday cookie is rainbow cookies! Always so yummy!
hi, without a doubt my favorite cookie is and always has been frosted sugar cookies, thanks
Oh my favorite is gluten free thumbprint cookies! My grandmother always made them when I was little and a favorite of mine! I missed them so much after being diagnosed with Celiac disease. I am loving all the new flours…so I can make them gluten free for me! Such beautiful memories!
That is so wonderful Laura!
My first year doing cookie swap I was given these mouthwatering cookies and cream cookies. They were so delicious I ate them up so fast but unfortunately have lost the recipe.
Well if you find that recipe, you’ll have to share Carrie-anne!
How creative!! Loving the idea of mint chocolate chip brownie cookies. My taste
buds are craving…
The lemon filled gingerbread cookies sound delicious! I’m a huge fan of anything lemon, especially sweets! Enjoy Life cookies are a family favorite too. I’ll definitely have to try the lemon filling with the sugar crisp cookies. Thanks for sharing!
They used to have a “Lively Lemon” soft cookie, did you ever get to try that one Lacy? I thought it was quite good, bummer it was discontinued!
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Can’t beat cut-out cookies!
My son really likes the enjoy life sugar cookies I think the lemon filling would be good in between them or the recipe for the whip cream the you have for Mini Apple pies from thanksgiving. Yummm?
Mmm, yes, that would be good!
My favorite holiday cookie is buckeyes (I’m from Ohio, I think some other people call them chocolate covered peanut butter balls). I make them dairy free, which still tastes just as yummy as the original, in my opinion. That being said, I also love all things pumpkin. I don’t usually get to eat very many holiday cookies because no one I know bothers to make them dairy free. I haven’t seen any of the enjoy life soft cookies around here. I would love to try them. Honestly, it’s difficult for me to find any dairy free products to enjoy. So, without tasting them, it’s hard to suggest a flavor, but I think pumpkin would go well with snickerdoodles (or gingerbread, but I like snickerdoodles better). I think a pumpkin pie dip kind of filling would be good or maybe a pumpkin cheesecake filling. Pumpkin doodles.
Or the crispy vanilla honey or sugar cookies would be good too.
I love buckeyes! I actually have a dairy-free version in my book, actually, too. Sounds like we’re on the same page Barbara 🙂 Their soft-baked cookies are so unique, yet addictive, very hard to describe. Yet even people who don’t follow any type of special diet love them. They’re just so darn soft, chewy and flavorful!