Red Velvet Wreath Whoopie Pies with Winter Berries & Cream

Make the Cream Cheese Frosting

10. Beat cream cheese and butter: In a clean bowl, beat the softened cream cheese and butter together until smooth and creamy with no visible lumps. Use medium-high speed for about 2 minutes.
11. Add powdered sugar and vanilla: Gradually add the powdered sugar, mixing on low at first to avoid a sugar cloud, then increase speed to medium-high. Add the vanilla extract and beat until the frosting is fluffy and spreadable, about 1–2 more minutes.

Assemble the Whoopie Pies

12. Pair up cakes: Match cookies into similar-sized pairs for even stacking. If wreath-shaped, align holes for a clean presentation.
13. Fill and sandwich: Pipe or spoon a generous dollop of cream cheese frosting onto the flat side of one cookie. Gently press the matching half on top to form a sandwich. Repeat with remaining pairs.
14. Optional decoration: Add sugared cranberries, fresh rosemary sprigs, or edible glitter to the center for a festive wreath effect. You can also pipe small frosting stars around the top for a decorative border.

Serving & Storage

Serve immediately or chill briefly to allow the filling to firm up. These whoopie pies are best enjoyed within 2–3 days. Store in an airtight container in the refrigerator; bring to room temperature before serving for ideal texture.

For make-ahead prep, unfilled cookies can be baked a day ahead and stored tightly covered. The frosting can be made in advance and refrigerated; bring it back to a spreadable consistency before assembling.