This cherry shortbread cookie has been one of my favorite nostalgic bakes for as long as I can remember. I first made a version of these during a holiday cookie swap years ago when I wanted something that tasted old-fashioned but still felt playful. The outside is tender and buttery with that melt-in-your-mouth shortbread texture, and the surprise maraschino cherry at the center gives each bite a pop of sweet, bright fruit that family and guests always comment on. I discovered the simple combination of cornstarch and whipped butter creates an unbelievably delicate crumb; it was the kind of discovery that convinced me it should live in my baking rotation permanently.

I typically make a double batch for celebrations because they disappear within an afternoon. The cookies are deceptively simple: pantry staples plus a jar of maraschino cherries and a little almond extract to coax out that classic cherry-almond flavor pairing. They feel special enough for gifting yet easy enough to bake on a weekday afternoon with the kids. The gentle vanilla-almond aroma and the sight of glossy red centers peeking through pale shortbread make these a small, joyful baking ritual in our house.

Ingredients

• Unsalted butter: 1 cup (2 sticks), softened. Use high-quality European-style butter if you want a richer flavor; softened butter whipped until airy gives the shortbread its delicate texture.
• Powdered sugar: 1/2 cup. Confectioners' sugar dissolves into the butter for a smoother bite and a finer crumb than granulated sugar.
• Cornstarch: 1/4 cup. A small addition that lightens the structure and adds to the tender, shortbread-like melt.
• All-purpose flour: 1 1/2 cups. Use a spoon-and-level measure to avoid overpacking; this keeps the cookies tender rather than dense.
• Almond extract: 1 teaspoon. A little goes a long way — it pairs beautifully with cherry and lifts the overall flavor.
• Maraschino cherries: 1 jar plus 1 tablespoon of the jar liquid. Pat cherries dry before using so they don’t add excess moisture to the dough; reserve a tablespoon of liquid for the glaze.
• For the cherry icing: 1/2 cup powdered sugar, 1 tablespoon butter melted, and 1 tablespoon maraschino cherry juice (from the jar) to thin and color the icing.

Instructions

Prep the oven and cherries: Preheat the oven to 350°F (175°C). Line a baking sheet with parchment paper or lightly grease it. Lay out 20–25 maraschino cherries on a paper towel and press another towel on top to remove extra syrup — this prevents the centers from making the dough too wet. Whip the butter: Soften the butter in short bursts in the microwave (15–20 seconds) or leave at room temperature until very soft. Transfer to a large mixing bowl and whisk vigorously by hand for about 5 minutes until the butter lightens in color and becomes aerated (or use a stand mixer on medium-high for 3–4 minutes). Proper whipping traps air which contributes to the delicate texture. Mix dry and flavor components: Add the powdered sugar, cornstarch, flour, and almond extract to the whipped butter. Combine with a whisk or mixer on low, then increase speed and mix for another 3–4 minutes until the dough is homogenous, slightly sticky, and holds together when pressed. If it looks crumbly, a teaspoon of milk can bring it together — but typically it’s soft and pliable. Portion and fill: Using a 1-tablespoon cookie scoop (or a tablespoon measure), portion dough and level it. Press your thumb into the center to form a small well, place one dried maraschino cherry inside, then use extra dough from the edges or a second small scoop to cover the cherry. Gently roll into a smooth ball and place on the prepared baking sheet about 1–2 inches apart. Bake: Bake for 12–14 minutes, rotating the pan halfway if your oven has hot spots. Look for the bottoms to begin to lightly brown — the tops should remain pale. Allow cookies to cool on the pan for several minutes before transferring to a wire rack; they are fragile when warm. Prepare the cherry icing: Whisk 1/2 cup powdered sugar with 1 tablespoon melted butter and 1 tablespoon maraschino cherry juice until smooth. Transfer to a small plastic bag, snip a tiny corner, and drizzle over cooled cookies for a glossy finish. Alternative: slice-and-bake method: If you prefer cookies without cherries inside, shape the dough into a 1.5-inch log using plastic wrap and chill in the freezer 5–10 minutes until firm but not frozen. Slice into rounds with a sharp knife and bake 12–14 minutes as above.

Storage Tips

Store completely cooled cookies in an airtight container at room temperature for up to 4 days to preserve the tender texture. For longer storage, freeze flat on a tray until solid, then transfer to a freezer-safe container with parchment between layers for up to 3 months. Thaw at room temperature for 30–60 minutes; if you like the glaze fresh, wait to drizzle until after thawing. Avoid refrigeration — it dries these cookies out more quickly than room temperature storage.

Ingredient Substitutions

For a dairy-free version, substitute vegan butter with similar fat content and chill the dough slightly before shaping to firm it up — texture will be close but slightly less rich. To make them gluten-free, use a 1:1 gluten-free flour blend and add 1 tablespoon of tapioca starch to mimic the lightness cornstarch provides. If you don’t have almond extract, use 1 teaspoon of vanilla plus a scant 1/4 teaspoon of almond-flavoring oil or omit entirely for a classic butter-forward taste.

Serving Suggestions

Arrange these cookies on a simple white plate or a rustic wooden board. They pair delightfully with a cup of black tea or espresso for a balance of sweetness. For holiday trays, alternate with darker cookies to enhance the visual contrast of the pale shortbread and glossy cherries. Garnish with a few whole cherries and a sprig of fresh mint for color when serving at brunch or parties.

Cultural Background

Shortbread traces its roots to Scottish baking traditions where butter, sugar, and flour create a simple, rich biscuit. The addition of maraschino cherries and almond extract is a more modern American twist — a mid-century nod to jarred cherries as an easy, festive ingredient. Combining the classic shortbread technique with a preserved fruit center creates a hybrid that feels both heritage-driven and distinctly American in its convenience and visual charm.

Seasonal Adaptations

In winter, use spiced maraschino cherries or add a pinch of cinnamon to the dough for warmth. For spring and summer, top with a thin lemon glaze and a half-cherry for freshness. Swap the almond extract for orange extract around citrus season to give a bright, seasonal lift. You can also dye the glaze with a drop of food coloring for themed cookie platters.

Meal Prep Tips

Make dough ahead: prepare the dough and shape into logs for slice-and-bake in the morning, then chill until ready to bake. For gifts, freeze baked cookies on a tray and pack in waxed paper between layers; include a small note about thawing before serving. If you need perfect rounds, chill scooped dough balls briefly on the tray before baking to maintain shape and prevent excessive spreading.

These cookies manage to be both humble and festive — a small, bright bite that’s easy to share. Give them a try and personalize the fillings and glaze; once you start experimenting with flavors, they become wonderfully addictive to adapt and gift.