This Cherry Kiss cookie has been a holiday favorite at my kitchen table for years. I first stumbled on the idea during a holiday cookie swap when I wanted something that tasted like cherry pie but looked like a classic butter cookie. The resulting bite is soft, slightly crumbly, and studded with tiny pockets of maraschino cherry that give a burst of sweet tang. The small pop of cherry juice brightens the dough and the almond and vanilla extracts layer in a subtle, nutty note that pairs beautifully with the milk chocolate Kiss on top. It is the kind of cookie that invites conversation while warm from the oven and still manages to disappear from the platter before dessert is served.

I discovered this precise balance of ingredients when testing batches to get the texture just right. Too much cherry juice makes the dough sticky and slow to bake. Too little and the cherry is only decorative. By reserving 1 1/2 tablespoons of the jarred cherry juice and tossing the chopped cherries with a little flour, I learned that the cherries stay suspended in the dough without sinking to the bottoms of the cookies. These cookies are tender with a delicate crumb. The granulated sugar coating gives a slight crackle and sparkle that makes them feel festive. They are simple to make and excellent for gifts, parties, or a quiet afternoon with tea.

Ingredients

• Maraschino cherries: Use one 12 ounce jar and drain the cherries, reserving 1 1/2 tablespoons of the juice for the dough. Choose bright, firm cherries rather than very soft ones and pat dry to avoid adding excess moisture to the dough.
• All purpose flour: Two cups go into the dough and two tablespoons are used to coat the chopped cherries so they stay suspended and do not sink while baking. Measure flour by spooning into the cup and leveling for accuracy.
• Salt: One half teaspoon of table salt balances the sweetness and enhances the butter flavor. If using salted butter, reduce slightly to taste.
• Unsalted butter: One cup at room temperature creates a tender, rich crumb. Choose a good quality butter such as Plugra or Kerrygold for deeper flavor.
• Powdered sugar: One cup sifted produces a fine texture in the dough and helps the cookies spread minimally for a thick, tender bite.
• Maraschino cherry juice: The reserved 1 1/2 tablespoons add flavor and a touch of color. Use the juice from the same jar of cherries for the best match.
• Almond and vanilla extract: Half teaspoon of each. Almond extract pairs particularly well with cherry and amplifies that maraschino flavor.
• Red food coloring: Four to six drops optional if you want a pink hue. Start with fewer drops and add more to reach the shade you prefer.
• Granulated sugar: One quarter cup for rolling gives the cookies a pretty sparkle and a subtle crunch.
• Hershey's Kisses: Thirty six pieces, one for each cookie, pressed into the warm cookie to finish.

Instructions

Preheat and prepare baking sheets:Preheat the oven to 350 degrees Fahrenheit. Line two large baking sheets with parchment paper to prevent sticking and to promote even browning. Lining two sheets speeds up baking by allowing you to switch racks midway if needed.Drain and prep cherries:Drain the jar of maraschino cherries into a small bowl, reserving exactly 1 1/2 tablespoons of the juice for the dough. Pat the cherries dry gently with paper towels to remove excess liquid. Finely chop the cherries and toss them with 2 tablespoons of all purpose flour. The light coating prevents them from bleeding into the dough and helps them distribute evenly when mixed.Combine dry ingredients:Whisk together the remaining 2 cups of all purpose flour and 1/2 teaspoon salt in a bowl and set aside. This ensures even seasoning and prevents pockets of salt in the dough.Cream butter and sugar:In a large mixing 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 as needed to ensure even creaming. Proper creaming traps air and contributes to a light texture.Flavor the butter: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 the mixture is fully incorporated and shows a uniform pale pink color if you used juice and coloring.Add dry ingredients:With the mixer on low speed, slowly add the flour and salt mixture, mixing only until the flour disappears. Over mixing will develop the gluten and make cookies tough. The dough will be stiff and slightly sticky but should hold a shape when scooped.Color and fold in cherries:If using food coloring, start with 2 to 3 drops and mix until even. Add 1 to 2 more drops if you want a deeper pink. Using a rubber spatula, fold in the reserved floured cherries until evenly distributed. Check for any large pockets of juice and blot if needed.Scoop and sugar coat:Using a 1 tablespoon cookie scoop, portion level amounts of dough and roll into smooth balls with your hands. Roll each ball lightly in 1/4 cup granulated sugar to coat and place on the prepared sheets 1 1/2 to 2 inches apart. You should fit about 12 to 15 cookies per large sheet.Bake and top:Bake in the center of the oven for 10 to 12 minutes or until the bottoms are just lightly golden. Remove from oven and gently press one Hershey's Kiss into the center of each warm cookie. Press just enough to slightly spread the cookie and to seat the candy so it will not fall off as it cools.Cool:Allow the cookies to cool on the baking sheets for 10 minutes so they set around the chocolate. Transfer to a wire rack to cool completely before serving or packing.

Storage Tips

Store cooled cookies in an airtight container layered with parchment or wax paper at room temperature for up to one week. If you want to preserve the crisp sugar exterior, place a piece of paper towel under the lid to absorb any excess moisture. For longer storage, freeze baked cookies in a single layer on a sheet until solid then transfer to a freezer bag for up to three months. Reheat from frozen at 300 degrees Fahrenheit for 4 to 6 minutes to refresh the texture. If freezing unbaked dough balls, place them on a sheet until firm then bag. Add a minute or two to bake time when baking from frozen.

Ingredient Substitutions

If you need to avoid dairy, substitute a vegan butter stick measured cup for cup but expect a slightly different mouthfeel and spread. To make these gluten free, swap the all purpose flour for a 1 to 1 gluten free flour blend that contains xanthan gum and be mindful that texture will vary slightly. If almond extract is a concern, replace with an equal amount of extra vanilla extract. For a lower sugar version, reduce the granulated roll sugar to 2 tablespoons but know the exterior sparkle will be less pronounced.

Serving Suggestions

Serve these with a glass of cold milk, a cup of tea, or alongside a scoop of vanilla ice cream for an indulgent dessert. They look beautiful on a holiday platter with a dusting of powdered sugar or arranged in a tin with tissue paper for gifting. For a party, place them on a tiered server with small signs noting they contain cherries and a chocolate center. Pair them with complementary flavors like shortbread or lemon bars to balance sweetness.

Cultural Background

Cookies with a candy set in the center are a familiar form in American cookie traditions, especially around holidays. The concept of combining cherry and chocolate appears across many regional sweets, echoing classic European pairings like cherry almond cakes. Maraschino cherries themselves became popular in mid century American baking when they were preserved and widely distributed, creating the nostalgic flavor people now associate with holidays and soda fountain treats.

Seasonal Adaptations

For winter holidays keep the classic red color or swap Kisses for peppermint bark kisses for a festive touch. In spring, omit food coloring and use pastel sprinkles instead of granulated sugar for a lighter look. Swap the Hershey's Kiss for an unwrapped chocolate covered cherry candy for a more intense fruit and chocolate hit. Spices like a pinch of ground cinnamon can add warmth for autumn versions.

Meal Prep Tips

Form dough balls ahead and freeze them on a sheet for make ahead baking. Pack them in single layer boxes to maintain their sugar coating and place a piece of parchment between layers. When planning for an event, bake one day ahead and store in an airtight tin to allow flavors to meld. If transporting, use a shallow container with compartments or parchment layers to prevent the Kisses from being knocked off.

These cookies feel special yet are straightforward to make. They have become my go to cookie for gifting because they look attractive, store well, and bring that nostalgic flavor everyone seems to love. Try a small test batch first to tune bake time for your oven and to match the pink shade you prefer, then scale up for company.