This Cherry Kiss cookie has been a holiday staple in my kitchen for years, the kind of recipe I reach for when I want something that sings of nostalgia yet feels fresh on the plate. I first adapted this combination from a vintage cookie tin recipe during a December baking marathon; the dough came together easily, the little pops of maraschino cherries brightened both the flavor and the color, and once I pressed a warm Hershey’s Kiss into the center, the result looked like a dozen tiny, edible ornaments. The texture is tender and buttery with gentle chew, the cherries give bursts of sweet cherry juice, and the chocolate center melts just enough to create a gooey contrast to the sugar-crisp exterior.

I learned early on that a few simple technique choices make a huge difference: patting the cherries dry so they don't add excess moisture, tossing them in a touch of flour so they don't sink, and not overbaking the rounds so they remain soft under the crisp edges. When I make a batch for parties, neighbors always ask for the recipe, and kids crowd the cooling rack waiting for that moment you press the Kiss in the warm cookie—it's a small ritual that gets everyone smiling. Whether you bake them for a cookie swap, a school fundraiser, or a rainy afternoon, these cookies are approachable, forgiving, and delightful.

Ingredients

• Maraschino cherries: 3/4 cup finely chopped from a 12-ounce jar, reserved 1 1/2 tablespoons juice—choose a high-quality brand for less artificial flavor. Pat dry before chopping to avoid extra moisture and for better color and texture in the dough.
• All-purpose flour: 2 cups for the dough plus 2 tablespoons to toss with the chopped cherries—King Arthur or Gold Medal are dependable choices; spoon and level the cup for accuracy.
• Salt: 1/2 teaspoon—use fine salt like table or fine sea salt to distribute evenly in the dough.
• Unsalted butter: 1 cup (2 sticks), room temperature—soft but still slightly cool; if it's too soft the dough will spread too much in the oven.
• Powdered sugar: 1 cup, sifted—gives a tender crumb and matte finish; sifting eliminates lumps for a silkier creaming process.
• Maraschino cherry juice: 1 1/2 tablespoons reserved from the jar—this adds authentic cherry flavor; do not replace with almond extract alone.
• Almond extract: 1/2 teaspoon—adds a warm, nutty backbone that complements cherry; if allergic, increase vanilla by 1/4 teaspoon instead.
• Vanilla extract: 1/2 teaspoon—for depth and balance; pure vanilla provides the best aroma.
• Red food coloring (optional): 4–6 drops—start with 2–3 drops to tint the dough a light pink, adding more if you want a more vibrant color.
• Granulated sugar: 1/4 cup—for rolling the dough balls to give a slight crunch and shine to the exterior.
• Hershey’s Kiss chocolates: 36 pieces—unwrapped and ready to press into warm cookies for a classic finish.

Instructions

Preheat and prepare: Preheat the oven to 350°F. Line two large baking sheets with parchment paper and set aside. Position racks to allow even heat circulation; baking on the center rack gives the most uniform browning. Prep the cherries: Drain the jar of maraschino cherries, reserving 1 1/2 tablespoons of the juice. Pat the cherries dry with a paper towel to remove excess syrup—this prevents the dough from becoming too wet and keeps cookies from spreading excessively. Flour the cherries: Finely chop the cherries, add them to a small bowl and toss with 2 tablespoons of all-purpose flour. This light coating helps the cherries suspend in the dough rather than sinking to the bottom of each cookie during baking. Combine dry ingredients: Whisk the remaining 2 cups of flour and 1/2 teaspoon salt in a bowl and set aside. This ensures even distribution of salt through the dough and prevents pockets of unsalted flour. Cream butter and sugar: In a large mixing bowl, beat the butter and sifted powdered sugar on medium speed for 1–2 minutes until smooth and fluffy. Proper creaming traps air, resulting in a lighter texture—scrape the bowl once to ensure even mixing. Flavor the base: Add the reserved 1 1/2 tablespoons cherry juice, almond extract, and vanilla extract to the butter mixture. Beat until fully incorporated, scraping the sides so flavors are evenly distributed. Incorporate the flour: Slowly mix the flour-salt mixture into the butter mixture on low speed until just combined. The dough will be stiff—do not overmix. If using red food coloring, add 2–3 drops now, mix, then add up to 2 more drops if you want a deeper pink. Fold in cherries: Use a rubber spatula to gently fold in the floured, chopped cherries until evenly dispersed. Excess stirring will develop gluten and yield a tougher texture, so fold only until distributed. Scoop and roll: Using a 1 tablespoon cookie scoop, portion level amounts of dough. Roll each portion into a smooth ball, then roll lightly in granulated sugar to coat. Place 1 1/2 to 2 inches apart on the prepared sheets; a large baking sheet will hold 12–15 cookies comfortably. Bake: Bake in the center of the oven for 10–12 minutes, or until the bottoms are just lightly golden. Visual cues matter more than time—watch the edges for gentle color change to avoid overbaking. Add the Kiss and cool: Remove cookies from the oven and immediately press a Hershey’s Kiss into the center of each warm cookie. Press just enough to slightly spread the cookie and secure the candy on top. Allow cookies to cool on the sheet for 10 minutes, then transfer to a wire rack to cool completely.

Storage Tips

Store completely cooled cookies in an airtight container at room temperature for up to 3 days. To freeze, arrange cookies in a single layer on a sheet tray and flash freeze until firm, then transfer to a freezer-safe container with parchment between layers; they will keep for up to 3 months. To reheat from frozen, place on a baking sheet and warm at 300°F for 5–7 minutes or until the chocolate softens—this restores a just-baked texture without overcooking.

Ingredient Substitutions

If you prefer a nut-free option, omit almond extract and increase vanilla to 3/4 teaspoon—this keeps aromatic depth without introducing nut allergens. For a gluten-free version, substitute a 1-to-1 gluten-free flour blend and be mindful of cross-contamination with the cherries; you may need to add 1–2 tablespoons extra flour if the dough seems too soft. For a lower-sugar twist, swap half the powdered sugar for a confectioners-style erythritol, keeping in mind texture will be slightly drier.

Serving Suggestions

Serve slightly warm with a glass of cold milk or alongside coffee. For holiday presentation, arrange on a white platter dusted with powdered sugar and garnish with a sprig of fresh mint. These cookies pair well with shortbread and biscotti on a mixed cookie platter, and their bright color makes them an excellent choice for Valentine’s Day or festive cookie exchanges.

Cultural Background

The idea of pressing a chocolate into a soft cookie is a classic American technique that blends simple dough techniques with iconic chocolate brands. While many variations exist—thumbprint cookies, Lindt-studded rounds, and filled sandwich cookies—the Cherry Kiss is a playful twist that blends mid-century jarred cherry preserves with modern convenience, capturing a nostalgic flavor profile often found in community bake sales and family gatherings.

Seasonal Adaptations

In summer, swap maraschino cherries for chopped glacé cherries or quick-pickled cherries to reduce sweetness and add brightness. For winter, stir in 1/2 teaspoon orange zest and a pinch of cinnamon for warmth. Swap the Hershey’s Kiss for a peppermint chocolate in December for a festive variation with cool mint and cherry.

Meal Prep Tips

For make-ahead prep, shape dough into 1 tablespoon balls, arrange on a tray, and freeze until firm; store in labeled bags and bake from frozen, adding 1–2 minutes to the baking time. Alternatively, bake the cookies completely and freeze cooled rounds in stacks separated by parchment—thaw at room temperature and gently rewarm before serving for best texture.

These cookies are small joys: easy to make, easy to share, and full of flavor. Whether you bake them for an event or a quiet afternoon treat, they’re the kind of recipe that becomes part of your kitchen’s rhythm. Make a double batch and gift a dozen—watch them vanish.