- Roast the berries: Preheat the oven to 400°F. Line a rimmed baking sheet with parchment paper or a silicone baking mat. Roast the berries, stirring halfway through, until they’re soft and juicy, about 25-30 minutes.
- Scoop the roasted strawberries and juices onto a large plate to cool.
- Prepare the milkshakes: Combine roasted strawberries (should yield about 1 1/4 cups) and all additional ingredients into a blender and blend until smooth. If you like a thicker shake, this is a good time to add an additional scoop of ice cream.
- Serve in your favorite glasses. Enjoy immediately.