Cherry Winks
Classic Thumbprint Cookies with a Cherry on Top!
What Are Cherry Winks?
Cherry Winks are the quintessential American thumbprint cookie! These buttery, tender cookies have a sweet indentation filled with jam (usually cherry or strawberry), topped with a glistening maraschino cherry. They’ve been a holiday staple for generations and are perfect for cookie exchanges, gift boxes, or snacking. The name “winks” comes from the way the cherry peeks out from the center like a winking eye!
Ingredients
- 1 cup (2 sticks) unsalted butter, softened
- 1/2 cup powdered sugar
- 2 1/4 cups all-purpose flour
- 1/2 tsp salt
- 1 tsp vanilla extract
- 1/4 tsp almond extract
- 3/4 cup cherry jam or strawberry jam
- 36 maraschino cherries, drained
- 1/2 cup finely chopped walnuts (optional)
Step-by-Step Instructions
- Cream butter and sugar: In a large bowl, beat the softened butter and powdered sugar until light and fluffy, about 3 minutes. Add vanilla and almond extracts.
- Mix dry ingredients: In a separate bowl, whisk together flour and salt. Gradually add to the butter mixture, mixing on low until just combined.
- Chill the dough: Form the dough into a ball, wrap in plastic, and refrigerate for 1 hour. Cold dough is easier to shape and holds its form better during baking.
- Shape the cookies: Preheat oven to 350°F (175°C). Roll dough into 1-inch balls. If using walnuts, roll each ball in chopped walnuts before placing on a baking sheet.
- Create the wells: Use your thumb or the back of a teaspoon to press a small well in the center of each cookie. Don’t press all the way through to the bottom!
- Fill and bake: Fill each well with about 1/2 teaspoon of jam. Top with a maraschino cherry. Bake for 10-12 minutes until edges are lightly golden.
- Cool and serve: Let cookies cool on the baking sheet for 5 minutes, then transfer to a wire rack. Store in an airtight container for up to 5 days.
Pro Tips for Perfect Cherry Winks
- Don’t skip chilling: Cold dough is much easier to handle and won’t spread during baking. Minimum 1 hour in the fridge!
- Don’t overmix: Mix until just combined to keep the cookies tender and crumbly.
- Drain the cherries: Pat the maraschino cherries dry with paper towels so they don’t make the cookies soggy.
- Control the depth: Press firmly enough to create a well but not so hard that you poke through the bottom.
- Try different jams: Raspberry, strawberry, or apricot jam all work wonderfully. Mix it up!
Nutrition Facts (per cookie)
Fun Variations
Chocolate Cherry Winks: Add 2 tablespoons of cocoa powder to the dough for a chocolate twist.
Nutty Version: Roll each ball in finely chopped pecans or walnuts before pressing.
Berry Medley: Use a mix of different jam flavors — some with strawberry, some with raspberry.
Lemon Glaze: Drizzle a simple lemon glaze over cooled cookies for extra sweetness.