This Cherry Kiss Cookie has been a holiday favorite in my kitchen for nearly a decade. I first made it on an impulse the winter after I found a jar of maraschino cherries buried in my pantry; I wanted something nostalgic but a little more elegant than a plain sugar cookie. The combination of finely chopped cherries folded into a buttery, slightly almond-scented dough and the warm, melty Hershey’s Kiss pressed into the center created an instant crowd-pleaser. The cookies are tender with a delicate crumb, a subtle cherry tang, and a sweet chocolate center that makes them feel special without requiring complicated decorating.

I often bring a tin of these to neighborhood potlucks and family gatherings because they travel well and always disappear first. The texture is what sells them: the dough is soft and lightly crumbly, the cherries add little bursts of concentrated syrup, and the granulated sugar coating gives a faint, pleasant crunch. The recipe is simple enough for beginners yet offers small techniques — like tossing the cherries in flour to prevent sinking and reserving cherry juice to infuse flavor — that make the final result reliably excellent. Every bite somehow tastes both classic and a little gourmet, which is why I keep this recipe in my go-to rotation for celebrations and weekday cookie cravings alike.

Ingredients

• Finely chopped maraschino cherries (3/4 cup): Drain a 12-ounce jar and finely chop the cherries. Pat dry on paper towels and toss with 2 tablespoons of flour so they don’t sink in the dough. Choose bright, firm cherries for texture.
• All-purpose flour (2 cups + 2 tablespoons): Use 2 cups for the dough and 2 tablespoons to coat the cherries. Measure flour by spooning into the cup and leveling off for accuracy; brands like King Arthur or Gold Medal are reliable.
• Salt (1/2 teaspoon): Balances sweetness and strengthens the dough structure.
• Unsalted butter (1 cup, room temperature): High-quality butter such as Plugrá or Kerrygold adds richness; allow to soften to room temperature so it creams smoothly with powdered sugar.
• Powdered sugar (1 cup, sifted): Sifting prevents lumps and creates a silky texture when creamed into the butter.
• Reserved maraschino cherry juice (1 1/2 tablespoons): Adds a concentrated cherry note; don’t add more or the dough may become too loose.
• Almond extract (1/2 teaspoon): A small amount amplifies the cherry flavor and gives a subtle marzipan nuance.
• Vanilla extract (1/2 teaspoon): Rounds out flavor; use pure vanilla when possible for depth.
• Red food coloring (4 to 6 drops, optional): Use sparingly to tint the dough pink if desired; gel color concentrates better than liquid.
• Granulated sugar (1/4 cup): For rolling the dough balls to create a delicate crunchy exterior.
• Hershey’s Kiss candies (36): One per cookie; unwrap and press into warm cookies immediately after baking.

Instructions

Preheat and prepare: Preheat the oven to 350°F and line two large baking sheets with parchment paper. Proper preheating ensures even spread; use the center rack for both sheets, and rotate mid-bake if your oven runs hot. Ensure sheets are cool and flat to avoid uneven baking. Drain and prep cherries: Drain the 12-ounce jar of maraschino cherries, reserve 1 1/2 tablespoons of juice, then pat the cherries thoroughly dry with paper towels. Finely chop them and toss with 2 tablespoons of flour. The flour coating prevents the cherries from bleeding through and sinking in the batter. Combine dry ingredients: Whisk 2 cups of all-purpose flour with 1/2 teaspoon salt in a medium bowl and set aside. Sifting or whisking distributes the salt evenly and aerates the flour for a lighter dough. Cream butter and sugar: In a large bowl, beat 1 cup room-temperature unsalted butter with 1 cup sifted powdered sugar on medium speed for 1 to 2 minutes until smooth and fluffy. Scrape the bowl to ensure even creaming; this step traps air and gives a tender texture. Add liquids and flavorings: Add the reserved 1 1/2 tablespoons cherry juice, 1/2 teaspoon almond extract, and 1/2 teaspoon vanilla extract to the creamed butter. Beat until fully incorporated. If using color, add 2 to 3 drops, mix, and add another drop or two to reach a pale pink tone; over-coloring can make the dough appear artificial. Incorporate flour and cherries: Slowly add the flour mixture on low speed until just combined; the dough will be stiff. Fold in the chopped cherries with a rubber spatula, distributing them evenly without overworking the dough, which can toughen the texture. Scoop and sugar-coat: Using a 1 tablespoon cookie scoop, portion level scoops of dough and roll into smooth balls. Roll each ball lightly in 1/4 cup granulated sugar to coat, then arrange 1 1/2 to 2 inches apart on prepared sheets. This spacing prevents cookies from fusing together while allowing a small spread. Bake and top with chocolate: Bake in the center of the oven for 10 to 12 minutes or until the bottoms show a faint golden edge. Remove from oven and immediately press one Hershey’s Kiss into each cookie, careful not to push it all the way through. Let cookies cool on the sheet for 10 minutes to set the chocolate, then transfer to a wire rack.

Storage Tips

Store cooled cookies in a single layer or with parchment between layers in an airtight container at room temperature for up to three days. For longer life, refrigerate up to seven days; bring to room temperature before serving so the chocolate regains its shine. To freeze, place cookies on a baking sheet until firm, then transfer to a freezer-safe container with parchment between layers and freeze for up to three months. Thaw in the refrigerator overnight or at room temperature for a few hours. Avoid storing near strong odors since the cherries and butter can absorb scents.

Ingredient Substitutions

If you don’t have maraschino cherries, chopped glacé cherries or candied cherries can work but expect slightly less juice and a denser chew. To make these nut-free, omit almond extract and increase vanilla to 1 teaspoon for balance. For a lower-sugar option, reduce granulated sugar for rolling or replace powdered sugar with a superfine sugar substitute designed for baking, though the texture will be slightly different. Use salted butter if necessary, but reduce added salt to 1/4 teaspoon. Gel food color provides more concentrated pink without adding liquid.

Serving Suggestions

Serve these warm for the best chocolate-soft experience, on a platter with sprigs of fresh mint or powdered sugar dusted lightly over the tray. They pair beautifully with black tea, espresso, or a glass of cold milk. For holiday gatherings, arrange on a tiered cookie stand mixed with plain sugar cookies and shortbread; the cherry color makes them a decorative focal point. For an adult twist, serve with a small pour of dessert wine like Moscato or a cherry liqueur for complementary flavors.

Cultural Background

Cookies with a chocolate center have long been a staple in American cookie trays, evolving from simple thumbprint cookies filled with jam to more modern variations featuring chocolate candies. The Cherry Kiss is a contemporary twist that borrows from mid-century dessert traditions — jarred cherries and boxed candy were pantry favorites — and elevates them with fresh-cherry techniques like flour-tossing. This blend of convenience and careful technique reflects post-war home baking history where preserving texture and appearance became equally important as flavor.

Seasonal Adaptations

In summer, swap maraschino cherries for quick macerated fresh cherries mixed with a teaspoon of sugar and a splash of lemon; reduce added juice accordingly. For winter, add 1/4 teaspoon of ground cinnamon or a pinch of nutmeg to the dough for warm spice notes. At Valentine’s Day double the almond extract to 1 teaspoon and use heart-shaped Kisses for a themed presentation. During Christmas, fold in 1/4 cup finely chopped toasted almonds (if no allergies) for extra crunch and flavor complexity.

Meal Prep Tips

To save time, chop the cherries and toss them in flour a day ahead, storing them in an airtight container in the refrigerator. The dough can be mixed and held covered in the fridge for up to 24 hours, which allows the flavors to meld and makes scooping easier. For frozen make-ahead cookies, form and sugar-coat dough balls, flash-freeze on a sheet, then store in a freezer bag; bake from frozen adding 1 to 2 minutes to the bake time and press Kisses in immediately after baking. Label containers with freeze dates and bake temperatures for convenience.

Success Stories

One memorable time I brought these to a community bake sale, a grandmother came back to my table after trying one and said it reminded her of the cookies she used to make with her mother. Another time a college friend requested them for a farewell box because they stayed soft even after a road trip. Those moments — seeing a simple cookie evoke nostalgia and bring comfort — are why I keep refining this recipe.

These cookies are easy to make, reliably delicious, and wonderfully adaptable. Whether for a casual coffee or a special celebration, they bring bright cherry flavor and a satisfying chocolate finish to the table — I hope they become a favorite in your home, too.