“Cherry Square” Cookies
If you grew up eating cherry squares at family holidays, this cookie version is going to hit you right in the nostalgia. These soft, yellow cake–style sugar cookies have a tender crumb, a sweet cherry center, and a snowy dusting of powdered sugar — just like the original dessert, but in hand-held form. They’re easy to make from scratch (no cake mix here), freeze beautifully for holiday baking, and are perfect for gifting, cookie swaps, or adding something a little different to your Christmas spread.
"Cherry Square" Cookies
The cookie version of one of my favorite childhood desserts, cherry squares! Super soft sugar cookies with cherries in the center, and dusted with powdered sugar.
Ingredients
- ¾ cup (150 g) granulated sugar
- ½ cup (113 g) unsalted butter, room temperature
- 1 large egg + 1 egg yolk, room temperature
- 1 teaspoon vanilla extract
- 1 ½ cups (180 g) cake flour
- 1 tablespoon cornstarch
- ½ teaspoon baking powder
- ¼ teaspoon baking soda
- ½ teaspoon salt
- 2 tablespoons milk
- 1 can cherry pie filling (you’ll only use the cherries, not all the gel)
- Powdered sugar, for dusting
Instructions
- Spoon the cherry pie filling into a fine-mesh strainer set over a bowl.
- Let it drain at least 30 minutes, gently stirring once or twice.
- Transfer cherries to a plate and blot lightly with paper towels.
- Cream butter and sugar together for 2–3 minutes until pale and fluffy, then beat in the egg, egg yolk, and vanilla until smooth.
- In a separate bowl, whisk together cake flour, cornstarch, baking powder, baking soda, and salt.
- Add dry ingredients to wet ingredients, mixing just until combined.
- Mix in the milk. Dough should be soft, creamy, and scoopable—almost like thick frosting.
- Cover and chill dough 30–45 minutes. (This helps keep the cookies thick and soft.)
- Once done chilling, preheat oven to 350°F (175°C). Line baking sheets with parchment. Then scoop 2-tablespoon portions of dough and roll gently into balls. Place on baking sheet, spacing 2½ inches apart.
- Use your thumb or the back of a teaspoon to make a shallow indentation in the center of each cookie, then place one well-drained cherry into each indentation. Don’t press all the way through.
- Bake for 11–13 minutes, until: edges are set, the tops look matte, and the bottoms are just barely golden. The centers should look soft and slightly underbaked—that’s the yellow cake magic.
- Cool cookies completely on the baking sheet. Dust generously with powdered sugar right before serving.
Notes
If wanting to freeze and bake later, follow steps 1-6 (but don't preheat the oven), Do NOT indent yet, then place dough balls on a parchment-lined baking sheet, and reeze until solid, about 1–2 hours. Once frozen, transfer frozen dough balls to a freezer-safe zip-top bag or airtight container, and label with: cookie name, oven temp (350°F), and bake time (13–15 min from frozen)
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There are certain recipes that instantly take you back to being a kid — standing in the kitchen while someone you love pulls a pan from the oven, powdered sugar floating through the air like edible snow. For my family, that dessert has always been cherry squares.
If you’ve never had them, cherry squares are beautifully simple: a yellow cake baked in a cookie sheet pan, cherry pie filling dotted across the top so every slice gets its own little pocket of fruit, and a generous dusting of powdered sugar once everything cools. No frosting, no fuss. Just sweet, soft cake and tart cherries. They showed up at holidays, potlucks, and random family gatherings, and somehow always disappeared faster than anything else on the table.
As someone who loves honoring family recipes (and maybe tweaking them just enough to make them my own), I’ve been itching to turn those cherry squares into a cookie for a while now. Something you could tuck into a Christmas cookie box, stack on a platter, or wrap up for a friend. A cookie that still felt nostalgic and familiar — not trendy or overcomplicated — but just as comforting as the original dessert.
And that’s exactly how these Cherry Square Cookies came to be.
Instead of a sheet pan cake, we’re making a soft sugar cookie with a subtle yellow cake vibe. Think tender crumb, buttery vanilla flavor, and just enough richness to feel bakery-worthy without being heavy. Each cookie gets a cherry tucked into the center, then a snowy dusting of powdered sugar once cooled. They look festive without needing sprinkles or icing, and they taste like the kind of dessert you’d expect to find on your grandma’s table.
The key to getting that “yellow cake” texture without using cake mix comes down to a few small choices: cake flour for tenderness, a little cornstarch for softness, and an extra egg yolk for richness and color. A splash of milk helps keep the dough creamy and soft, so the cookies bake up pillowy instead of crisp. The result is a cookie that almost eats like a mini cake — exactly what we’re going for here.
For the cherry center, I use classic canned cherry pie filling, but with one important step: draining it well. You want the cherries, not all the gel, so they don’t bleed into the dough or make the centers soggy. Once drained and lightly blotted, the cherries bake beautifully and stay juicy without overpowering the cookie.
One of my favorite things about this recipe is how practical it is for holiday baking. These cookies were designed with Christmas cookie boxes in mind. The dough freezes incredibly well, which means you can make it once, portion it out, and bake fresh batches throughout the week as you’re visiting friends and family. Fresh-baked cookies always feel extra special, and this method keeps the texture perfect every single time.
When baking from frozen, you simply let the dough balls sit out for a few minutes, make the indentation, add the cherry, and bake. No complicated thawing schedules or last-minute stress. Just warm cookies, powdered sugar on your sweater, and the smell of vanilla in the kitchen — exactly how holiday baking should feel.
These cookies also hold up nicely once baked. They stay soft for several days at room temperature, making them ideal for gifting or setting out on a dessert table. I recommend dusting them with powdered sugar right before serving or boxing so they keep that fresh, snowy look.
Flavor-wise, they’re sweet but not cloying, with just enough tartness from the cherry to balance everything out. If you want to lean slightly more bakery-style, you can add a tiny splash of almond extract to the dough — it plays beautifully with the cherry without overpowering the classic vibe.
Mostly though, I love how these cookies keep the heart of the original cherry squares alive. They’re familiar, comforting, unfussy, and meant to be shared. The kind of recipe that feels just as appropriate on a fancy holiday platter as it does on a paper plate in a busy kitchen full of people you love.
If you’re building your holiday baking lineup this year, I really hope these make the cut. They’re a little different than the usual sugar cookies or chocolate crinkles, but still approachable and crowd-pleasing — the best kind of addition to any cookie box.
And if you grew up with a dessert like cherry squares in your own family, I’d love to hear about it. Those recipes are the ones worth preserving, reinventing, and passing along — powdered sugar and all.
