I’ve baked dozens of cookie recipes over the years, but this 1 recipe is most requested year over year!

These Raspberry Shortbread Cookies with Raspberry Filling and Vanilla Drizzle are a cherished delight in our family, perfect for any occasion that calls for a little homemade comfort. This recipe harks back to the sweet treats my grandmother used to make for us during the summer, using fresh raspberries picked from the farm. The combination of buttery shortbread, tangy raspberry filling, and the sweetness of vanilla drizzle makes these cookies irresistible. Whether you’re planning a cozy gathering or simply want to treat yourself, these cookies are a lovely way to celebrate simple joys.

These cookies are lovely on their own with a hot cup of tea or coffee. If you’re feeling indulgent, a scoop of vanilla ice cream on the side pairs beautifully with the tangy raspberry filling. For a special treat, serve them with a dollop of whipped cream and a few fresh raspberries. These cookies are also wonderful additions to a dessert platter with other classic Midwestern baked goods like apple pie or molasses cookies.

1 cup (2 sticks) unsalted butter, softened
1/2 cup powdered sugar
1 teaspoon vanilla extract
2 cups all-purpose flour
1/2 cup raspberry jam or preserves
1 cup powdered sugar (for drizzle)
2-3 tablespoons milk (for drizzle)
1/2 teaspoon vanilla extract (for drizzle)