This Cherry Kiss cookie is one of those nostalgic recipes that turns up every holiday season at my house. I first discovered this combination years ago while rooting through my grandmother's recipe box; she used to tuck a single chocolate kiss into the center of a small, buttery cookie and everyone would wait impatiently for them to cool so they could bite through warm chocolate and soft cookie. The bright, sweet pop of maraschino cherries folded into a tender dough gives the cookie a cherry-laced surprise in every bite while the Kiss on top melts just enough to become a glossy centerpiece.

What makes these gems special is the contrast of textures and the gentle almond note from a dash of extract that plays beautifully with cherry and milk chocolate. I learned to finely chop the cherries and toss them in a touch of flour so they do not sink or bleed throughout the dough. The result is a cookie that is delicate, slightly crumbly at the edges and soft in the center, with a subtle pink hue if you choose to tint the dough. They are a repeat request for potlucks, cookie exchanges and winter gatherings—easy to make in large batches and delightful to plate for guests.

Ingredients

• Maraschino cherries: Use 3/4 cup finely chopped maraschino cherries drained from a 12-ounce jar and reserve 1 1/2 tablespoons of the cherry syrup. Pat the cherries dry with paper towels before chopping to prevent excess moisture from affecting dough.
• All-purpose flour: 2 cups for the dough and an extra 2 tablespoons to toss with the chopped cherries so they distribute evenly and do not sink while baking. King Arthur or Gold Medal work well for reliable structure.
• Unsalted butter: 1 cup at room temperature. Using unsalted butter lets you control salt; if you only have salted, reduce added salt slightly.
• Powdered sugar: 1 cup sifted for a melt-in-your-mouth texture in the dough; this also helps keep the cookie tender compared with granulated sugar in the dough itself.
• Granulated sugar: 1/4 cup for rolling the cookie balls to provide a slight sparkle and a touch more crunch on the exterior.
• Extracts & optional color: 1/2 teaspoon almond extract and 1/2 teaspoon vanilla extract for depth of flavor and 4 to 6 drops red food coloring if you want a light pink cookie dough.
• Salt: 1/2 teaspoon to balance the sweetness and enhance the other flavors.
• Hershey’s Kisses: 36 pieces to top each cookie with a small milk chocolate center that softens slightly when pressed into warm dough.

Instructions

Prepare and drain cherries: Drain the 12-ounce jar of maraschino cherries, reserving 1 1/2 tablespoons of the juice for the dough. Pat the cherries dry with paper towels to remove excess syrup; excess liquid will make the dough loose. Finely chop the cherries so they disperse in small pockets rather than large chunks. Toss cherries with flour: Place the chopped cherries in a small bowl and toss with 2 tablespoons of all-purpose flour. This little trick coats the fruit and prevents the red juice from bleeding through the dough and helps them distribute evenly during mixing. Mix dry ingredients: Whisk together the remaining 2 cups of all-purpose flour and 1/2 teaspoon salt in a medium bowl. Set aside so the dry mix is ready to be added in one go for even incorporation. 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 to 2 minutes until pale and fluffy. Proper creaming traps air and helps with a lighter crumb. Add cherry juice and extracts: Blend the reserved 1 1/2 tablespoons maraschino cherry juice, 1/2 teaspoon almond extract and 1/2 teaspoon vanilla extract into the creamed butter. Mix until fully incorporated. If you choose to color the dough, add 2 to 3 drops of red food coloring now and add more drops until you reach the desired pink shade. Combine dough: With the mixer on low speed, slowly add the flour mixture and mix just until the flour is incorporated. The dough will be stiff; stop mixing as soon as there are no visible streaks of flour to avoid overworking gluten. Fold in cherries: Use a rubber spatula to gently fold the reserved floured, chopped cherries into the dough, scraping the bottom and sides of the bowl to distribute evenly without crushing the fruit. Scoop and roll: Using a 1-tablespoon cookie scoop, portion level scoops and roll gently between your palms to form smooth balls. Roll each ball lightly in 1/4 cup granulated sugar to coat then place on parchment-lined baking sheets 1 1/2 to 2 inches apart. Bake and press chocolate: Bake in a preheated 350°F oven for 10 to 12 minutes until the bottoms are just lightly golden. Remove sheets from the oven and immediately press one Hershey’s Kiss into the center of each warm cookie so it adheres but does not sink completely. Allow cookies to rest on the sheets 10 minutes before transferring to a wire rack to cool completely.

Storage Tips

Store cooled cookies in an airtight container at room temperature for up to 4 days. If stacking cookies, place a sheet of parchment between layers to avoid smudging the Hershey’s Kisses. For longer storage, freeze baked cookies in a single layer on a sheet tray until firm, then transfer to a freezer-safe container for up to 3 months. To reheat frozen cookies, let them come to room temperature or warm them briefly in a 300°F oven for 5 minutes to regain a just-baked texture.

Ingredient Substitutions

If you prefer a dairy-free version, swap the butter for a one-to-one plant-based margarine and choose dairy-free chocolate discs instead of Hershey’s Kisses. For a gluten-free option use a certified 1:1 gluten-free flour blend, but be mindful that texture can change slightly—add 1 to 2 tablespoons of additional flour blend if the dough feels too soft. To amplify cherry flavor without additional sugar, fold in 1 tablespoon of cherry preserves and reduce reserved cherry juice accordingly.

Serving Suggestions

Serve these cookies on a festive platter lined with lace paper doilies for parties or pack them in small tins as edible gifts. Pair with a hot cup of coffee, a glass of milk or even a lightly sweetened cocoa for a cozy dessert. Garnish the tray with a few fresh cherries or sprigs of mint for contrast. For a brunch spread, place them next to scones and a fruit salad for a sweet finish.

Cultural Background

Cookies topped with a chocolate kiss have roots in American baking traditions of the mid-20th century where candy-topped cookies became popular for their simplicity and visual appeal. Adding maraschino cherries is a nod to classic holiday baking that embraces bright colors and easily sourced jarred fruit. Over generations this pairing has become a comfort-bake classic at many family gatherings and cookie exchanges across the United States.

Seasonal Adaptations

For winter holidays, tint the dough a light pink to deep rose with food coloring or add a few festive sprinkles before pressing the chocolate. In summer, substitute some of the cherries with chopped candied cherries or dried cherries rehydrated briefly to keep the bright fruit flavor. For Valentine’s Day, use red or pink-colored sugar for rolling and try dark chocolate kisses for a richer contrast against the sweet cherry.

Meal Prep Tips

Make a double batch of dough, portion with a cookie scoop and freeze the uncooked dough balls on a sheet pan. Once frozen, store in airtight bags—bake directly from frozen adding a minute or two to the baking time. This saves time on busy mornings or when unexpected guests arrive. Store cooled cookies in shallow airtight containers with parchment between layers to maintain the crisp edges and soft centers.

These Cherry Kiss cookies are a comforting, giftable and crowd-pleasing treat. They are forgiving to make and delightful to share — now it’s your turn to make them a tradition in your kitchen.