The Chocolate Sandwich Cookies I Beg My Sister to Bake Every Year

The perfect holiday treat for everyone on your list.

December 21, 2018
Photo by Posie Brien

My favorite gift from my younger sister is cookies. Chocolate sandwich cookies to be exact. When we were in high school, she uncovered—and perfected—a recipe for homemade Oreos. I can picture her in the kitchen, earnestly focused on filling each cookie with a generous dollop of buttercream. I'd beg her to make them when we were home together.

Ever since then, she'll occasionally surprise me with a package of them in the mail. When I see a box outside my door with her return address in Maine, I hold my breath hoping it's cookies. I unpack them and store them in the freezer. I savor each one, eating them in tiny bites to make them last. I love how good they taste: the rich chocolate wafers, the sweet filling with a touch of vanilla and salt to balance the sugar. I love that the cookies are crisp on the edges and slightly soft in the center so they don't shatter too much under your teeth. And, most of all, I love that they're a labor of love.

There are so many homemade goodies that make excellent gifts. You can make your own caramels, wrap up miniature pound cakes, or pack a jar with your own cocktail cherries. But I believe there's something especially alluring about homemade sandwich cookies, and not just because of my sister. (Although that helps!)

The nostalgia of faux Oreos appeals to just about everyone, and with this recipe, you can customize them with fun fillings. I can't imagine anything more whimsical for the holidays.

Basically Christmas magic. Photo by Posie Brien

I've tried all manner of fillings from birthday cake (flavored with imitation vanilla and sprinkles) to dark chocolate espresso. But my top three favorites are whipped tahini (like a more sophisticated cousin of a peanut butter filling), peppermint (because what's better for the holidays?), and matcha white chocolate (a wildly green creation that will win over every kid on your list).

Start with the base recipe for the cookies. Be sure to let them cool fully, then fill with your favorite frosting or filling.

Now, Pick Your Filling

Matcha White Chocolate Sandwich Cookie Filling

Peppermint Sandwich Cookie Filling

Whipped Tahini Sandwich Cookie Filling

What's your favorite holiday cookie? Share recipes in the comments section below!

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See what other Food52 readers are saying.

  • Kat
  • Posie (Harwood) Brien
    Posie (Harwood) Brien
I like warm homemade bread slathered with fresh raw milk butter, ice cream in all seasons, the smell of garlic in olive oil, and sugar snap peas fresh off the vine.


Kat November 13, 2019
I’d love to make this for work. I was wondering though, if I wanted to have the cookies be red or green velvet, is there a good way to achieve that? I think red and green cookies with a white icing inside might be a bigger hit with kids, but I’m not sure. I’m planning on using a button shaped cookie cutter to amp up the cute factor
Posie (. November 13, 2019
Instead of trying to adapt this cookie recipe, I think you'd be better off searching for a cookie recipe that's designed to be red velvet! I imagine red velvet cookies are best when they are cakier, more like a whoopie pie, so I'd search for that. Or, you could go the route of using food coloring in a classic roll-out sugar cookie recipe.