Preheat your oven to 350°F (175°C).
In a mixing bowl, cream together the butter and sugar until light and fluffy.
Add the eggs one at a time, beating well after each addition. Stir in the vanilla extract.
Combine the gluten-free flour and milk, and add to the mixture gradually, mixing well.
Pour the batter into cupcake liners and bake for 20-25 minutes or until a toothpick inserted into the center comes out clean. Let them cool completely.
Once cooled, crumble the cupcakes into pieces.
In a trifle dish, layer the crumbled cupcakes, whipped cream, and fresh berries. Repeat layers until the dish is filled.
Chill in the refrigerator for at least 1 hour before serving.