This Cherry Kiss cookie has been a holiday staple in my kitchen for as long as I can remember. I first encountered the idea at a neighborhood cookie swap the year I moved into my first apartment; the batch I brought disappeared before I finished the elevator ride home. I recreated the flavor and texture to suit our family: a tender, buttery cookie with finely chopped maraschino cherries throughout, a hint of almond and vanilla, and a single chocolate Kiss pressed into the center while the cookie is warm. The result is small, elegant, and intensely approachable — children love the bright pink flecks and adults nod approvingly at the buttery crumb with a sharp chocolate finish.

I usually make these for holiday trays and for potlucks because they travel well and look festive without requiring elaborate decoration. The dough is forgiving, and the cherries keep the cookies moist longer than a plain butter cookie. I reserve a tablespoon and a half of maraschino juice to add into the dough for an authentic cherry flavor; it’s a tiny trick that amplifies the cherry presence without making the dough wet. These cookies are excellent warm from the oven but also delicious at room temperature, and they freeze beautifully between layers of parchment in an airtight container.

Ingredients

• Maraschino cherries: Use a 12-ounce jar and reserve 1 1/2 tablespoons of the juice for the dough. Choose a brand you enjoy eating from the jar; good cherries are firm and not overly sweet. Pat dry and finely chop for even distribution.
• All-purpose flour: 2 cups for the dough, plus 2 tablespoons to toss with the chopped cherries so they don’t sink into the batter. Spoon and level the flour into the measuring cup for accuracy.
• Unsalted butter: 1 cup (two sticks), at room temperature. Real butter gives the best flavor and structure; do not substitute margarine.
• Powdered sugar: 1 cup, sifted to remove lumps for a smooth, tender crumb.
• Flavors: 1/2 teaspoon almond extract and 1/2 teaspoon vanilla extract to deepen the cherry taste; optional red food coloring, 4–6 drops, if you want a pink hue.
• Sugars and finishing: 1/4 cup granulated sugar for rolling the scooped dough; this gives a gentle sheen and a slight crisp edge.
• Chocolate centers: 36 Hershey's Kisses, unwrapped, for pressing into the warm cookies so they slightly spread and set on top.
• Salt: 1/2 teaspoon to balance the sweetness and brighten the flavor.

Instructions

Preheat and prepare: Preheat your oven to 350°F and line two large baking sheets with parchment paper. This prevents sticking and allows the bottoms to brown gently. Using two sheets keeps you from overcrowding and helps maintain even oven circulation. Drain and chop cherries: Drain the jar of maraschino cherries, reserving exactly 1 1/2 tablespoons of the juice. Pat the cherries dry on paper towels, then finely chop. Toss the chopped cherries with 2 tablespoons of the all-purpose flour to prevent sinking during baking. Combine dry ingredients: In a medium bowl, whisk together the remaining 2 cups of all-purpose flour and 1/2 teaspoon salt. Set aside so the flour is ready to incorporate evenly into the butter mixture. Cream butter and sugar: In a large mixing bowl, beat 1 cup room-temperature unsalted butter and 1 cup sifted powdered sugar with a handheld mixer on medium speed until smooth and fluffy, about 1–2 minutes. Proper creaming traps air for a lighter texture. Build the dough: 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 until fully incorporated. Add the flour mixture slowly on low speed until just blended; the dough will be stiff. If desired, add 2–3 drops of red food coloring and mix, adding up to 2 more drops to reach your preferred pink shade. Fold in cherries: Using a rubber spatula, fold the floured chopped cherries into the dough until evenly distributed, taking care not to overmix which could break down the cherries. Scoop and sugar coat: Using a 1 tablespoon cookie scoop, portion level scoops of dough and roll each into a smooth ball between your palms. Roll each ball lightly in 1/4 cup granulated sugar so the surface is evenly coated, then place 1 1/2 to 2 inches apart on the prepared sheets. Bake: Bake in the center of the oven for 10–12 minutes, or until the bottom edges are just lightly golden. The centers will look set but still soft; do not overbake or the cookies will lose their tender texture. Top with chocolate: Remove the cookies from the oven. Working quickly, press one unwrapped Hershey’s Kiss gently into the center of each warm cookie. Press just enough to slightly spread the cookie and allow the candy to rest on top as it cools. Cool: Let cookies cool on the baking sheets for about 10 minutes, then transfer to a wire rack to cool completely. This prevents the Kisses from sliding off and helps the cookie finish setting.

Storage Tips

Store cooled cookies in an airtight container at room temperature for up to five days. For longer storage, freeze in a single layer on a baking sheet until solid, then transfer to a freezer-safe container with parchment layers between rows. To serve from frozen, thaw at room temperature for about 30 minutes. Reheating briefly in a 275°F oven for 4–5 minutes revives the buttery texture and softens the chocolate slightly for a just-baked experience.

Ingredient Substitutions

If you prefer, substitute the all-purpose flour for a gluten-free 1:1 blend; results are best with a blend containing xanthan gum. Replace unsalted butter with European-style butter for a richer flavor, reducing added salt slightly. If nut allergies are a concern, omit the almond extract and add an extra 1/4 teaspoon vanilla instead. For a deeper chocolate note, swap Hershey's Kisses for mini semi-sweet chocolate chips (about 1 teaspoon pressed into each cookie).

Serving Suggestions

These bite-sized treats are perfect on holiday platters alongside spritz cookies and shortbread. Garnish a cookie tray with fresh cranberries and rosemary sprigs for festive color. For an afternoon tea, pair with black tea or a light roast coffee. Serve warm with a scoop of vanilla ice cream for a playful dessert: two cookies sandwiching a small scoop of ice cream is delightful.

Cultural Background

Bittersweet chocolate paired with cherries is a long-standing flavor pairing in Western baking, echoing the classic Black Forest combination. The idea of pressing a small chocolate into the center of a cookie is a modern twist on thumbprint confections that date back centuries; these tiny centers act as both ornament and flavor finish. This particular iteration — maraschino cherry in the dough and a chocolate top — became popular in mid-20th-century American home baking as commercially jarred cherries became widely available.

Meal Prep Tips

To prepare ahead, make and scoop the dough, place scooped balls on a parchment-lined tray, cover tightly, and refrigerate up to 24 hours before rolling in sugar and baking. Alternatively, freeze scooped dough balls on a sheet for up to 2 months; when ready, roll in sugar and bake directly from frozen, adding 1–2 minutes to baking time. Label containers clearly with baking times to avoid overbaking.

These cookies are one of those small, reliable joys: easy to make, easy to share, and always welcome at the table. I hope you enjoy making and giving them as much as my family and I do.