This Cherry Kiss cookie has been a joyful, slightly cheeky addition to my holiday baking rotation for years. I first made these on a snowy December afternoon when a jar of maraschino cherries in the pantry begged for a better purpose than topping sundaes. The result was a tender, buttery cookie with little pockets of bright cherry flavor that surprised everyone who tried one. The way the cherries punctuate each bite — soft, sweet, and slightly tangy — contrasts beautifully with the richness of the butter and the classic milk chocolate Kiss pressed into the center. They are small but celebratory, perfect for cookie exchanges, classroom parties, or a quiet cup of tea when you want something special but not fussy.

I love how approachable this recipe is. It relies on a few pantry staples and one jar of maraschino cherries, so you can pull it together without a long shopping list. The dough comes together quickly with a hand mixer and keeps a soft texture after baking — the edges just barely golden while the centers stay tender enough to hold a chocolate candy without cracking. These cookies evoke childhood holiday trays for me: the sticky cherry bits, the powdered sugar in the dough, and that tiny chocolate crown. Making them became our family ritual: my niece rolls the dough and I press the kisses in, and the kitchen always smells of butter and almond extract when we’re done.

Ingredients

• Maraschino cherries: 3/4 cup finely chopped (from a 12-ounce jar). Choose bright, plump cherries and drain them well — reserve 1 1/2 tablespoons of the jar juice for the dough to boost cherry flavor. Pat the cherries dry so they don’t add excess moisture to the dough.
• All-purpose flour: 2 cups for the dough plus 2 tablespoons to toss with the chopped cherries. The extra flour prevents the cherries from sinking and ensures even distribution through the dough. King Arthur or Bob's Red Mill work great here.
• Salt: 1/2 teaspoon. Balances sweetness and rounds the flavor; use fine sea salt for a clean finish.
• Unsalted butter: 1 cup (2 sticks), room temperature. Properly softened butter gives the cookies a tender, melt-in-your-mouth texture — don’t use melted butter.
• Powdered sugar: 1 cup, sifted. Adds to the delicate crumb and helps create a slightly tender, shortbread-like texture.
• Maraschino cherry juice: 1 1/2 tablespoons reserved from the jar. It adds real cherry aroma and a pale blush to the dough if you choose to color it.
• Almond extract: 1/2 teaspoon. A small amount of almond enhances the cherry notes — if you prefer, swap for 1 teaspoon amaretto liqueur for an adult twist.
• Vanilla extract: 1/2 teaspoon for warm depth and balance.
• Red food coloring (optional): 4–6 drops to tint the dough pink. Start with 2–3 drops and add more to reach the shade you want.
• Granulated sugar: 1/4 cup for rolling the dough balls — gives a slight crunch and sparkle to the exterior once baked.
• Hershey’s Kisses: 36 pieces, unwrapped. Use classic milk chocolate or swap to dark chocolate Kisses for contrast.

Instructions

Preheat and prepare baking sheets: Preheat the oven to 350°F. Line two large baking sheets with parchment paper and set aside so you can place the shaped cookies directly onto them. Using parchment prevents sticking and helps bottoms brown evenly. Prepare cherries: Drain the jar of maraschino cherries into a fine sieve, reserving 1 1/2 tablespoons of the juice for the dough. Pat the cherries dry with paper towels to remove excess syrup — moisture will make the dough too soft and cause spreading. Coat chopped cherries: Finely chop the drained cherries and toss them in 2 tablespoons of all-purpose flour in a small bowl. This coating prevents them from sinking and helps them disperse evenly throughout the dough during mixing. Mix dry ingredients: In a separate bowl whisk together the remaining 2 cups all-purpose flour and 1/2 teaspoon salt. Set aside so you can add it gradually to the butter mixture. Cream butter and powdered sugar: In a large bowl, beat 1 cup room-temperature unsalted butter and 1 cup sifted powdered sugar with a handheld mixer on medium speed for 1–2 minutes until smooth and fluffy. Proper creaming traps air, giving the cookies a lighter texture. Flavor the base: Add the reserved 1 1/2 tablespoons cherry juice, 1/2 teaspoon almond extract, and 1/2 teaspoon vanilla extract to the butter mixture. Beat again until fully incorporated; scrape the bowl to ensure even mixing. Combine dough: Slowly add the flour mixture while mixing on low speed just until combined. The dough will be stiff — avoid overmixing to prevent toughness. If using red food coloring, add 2–3 drops now, mix, and add more until you reach a soft pink. Fold in cherries: Using a rubber spatula, gently fold in the reserved chopped cherries until evenly distributed. The spatula helps keep the cherries intact and prevents breaking them into a paste. Shape cookies: Use a 1-tablespoon cookie scoop to portion level amounts of dough, then roll into smooth balls with the palms. Roll each ball in 1/4 cup granulated sugar to lightly coat and place 1 1/2–2 inches apart on prepared sheets. This spacing gives the cookies room to set without merging. Bake: Bake in the center of the oven for 10–12 minutes, or until the bottoms are just lightly golden and the tops are set but not browned. Tiny pale cracks on top are fine; they signal tenderness inside. Top with Kisses and cool: Remove cookies from the oven and immediately press one Hershey’s Kiss into the center of each warm cookie — press gently so the candy sits snugly on top without sinking through. Let cool on the baking sheet for 10 minutes, then transfer to a wire rack to cool completely before serving.

Storage Tips

Store completely cooled cookies in an airtight container layered with parchment to prevent sticking. At room temperature they remain fresh for about 3–4 days; move to the refrigerator for up to 7 days if you prefer the Kisses firmer. For longer storage, freeze baked cookies in a single layer on a tray until firm, then transfer to a freezer-safe bag for up to 3 months. Reheat briefly in a 300°F oven for 3–4 minutes to refresh the texture, or allow to come to room temperature if removing from refrigeration so the chocolate regains a pleasant chew.

Ingredient Substitutions

If you need dairy-free cookies, substitute a vegan butter stick one-for-one and use dairy-free chocolate kisses. For a gluten-free version, replace the all-purpose flour with a 1-to-1 gluten-free flour blend that contains xanthan gum; note the texture will be slightly crumblier. If almond extract is a concern for nut allergies, swap it for an equal amount of extra vanilla or 1 teaspoon finely grated orange zest for a citrus lift. To reduce sweetness, use darker chocolate for the Kisses and drain cherries thoroughly to avoid extra syrup in the dough.

Serving Suggestions

These are perfect on a holiday cookie platter alongside shortbread and spritz cookies. For a grown-up dessert, serve warm with a small scoop of vanilla ice cream; the contrast of warm cookie, cold ice cream, and melty chocolate is irresistible. Garnish with a light dusting of powdered sugar or a few extra chopped cherries for color. They pair beautifully with strong coffee, milky hot chocolate, or a bright, citrusy tea. Package a dozen in a small gift box with tissue for neighborly treats.

Cultural Background

Cookies that combine fruit and chocolate have long been a part of American holiday baking, with variations showing up in mid-20th-century cookbooks. The use of maraschino cherries became especially popular as commercially jarred cherries became widely available, lending an easy way to add bright color and sugary fruit flavor to baked goods. Pressing a chocolate into the center is a modern take on the classic thumbprint cookie — the Kiss topping evolved later as a convenient and festive choice that makes each cookie look like a little present.

Seasonal Adaptations

For winter holidays keep the cherries and Kisses as written; for Valentine’s Day use red or pink sprinkles and pink-tinted dough. In summer, swap maraschino cherries for chopped dried cherries rehydrated in a splash of orange juice and a tablespoon of granulated sugar — use the same flour dusting trick. For autumn, fold in a pinch of ground cinnamon and swap almond extract for a teaspoon of maple syrup to create deeper, warming notes consistent with seasonal flavors.

Meal Prep Tips

Portion dough into 1-tablespoon scoops and freeze on a tray, then transfer to a labeled freezer bag so you can bake fresh cookies a few at a time. When baking from frozen, add 1–2 minutes to the bake time and press the Kiss in while still warm. If you’re making multiple batches for an event, keep baked cookies in a single layer at room temperature and only press Kisses in when cookies are warm; this prevents the chocolate from dulling during extended storage.

Every time I bake these I’m reminded how small rituals — measuring, rolling, pressing the Kiss — become moments of connection. Whether you’re making them with kids, bringing them to a party, or baking quietly on a Sunday afternoon, they have a way of making the day feel a little sweeter. Try them once and I’m confident they’ll become a favorite in your repertoire.