To a medium saucepan, set over medium low heat, pour in the heavy cream, sugar and pinch of sea salt; stir until the sugar has dissolved, about 2 minutes.
To the jar of a blender, add the cherries and milk. Blend until very smooth about 1 minute. Place a sieve atop a large bowl and pour the puree through it, discarding the pulp. Add the sugar/heavy cream mixture to the bowl and mix until thoroughly combined. Cover the bowl with plastic wrap and refrigerate until very cold, at least 4 hours or overnight.
Churn the mixture in the bowl of your ice cream maker, according to your machine's instructions. Serve immediately for soft serve or alternatively transfer to a freezer-safe container and freeze overnight.
To make the streusel, start with preheat the oven to 350 degrees F. Line a baking sheet with parchment paper and set aside. Add the whole wheat flakes, sugar, all-purpose flour and salt to a medium bowl and toss together. Using a box grater, grate the cold butter atop the flour mixture; using your hands, break up the butter and distribute throughout. Pour the streusel on the prepared baking sheet and transfer to the oven for about 15 minutes. At the 15-minute mark, toss the streusel once and bake for an additional 15 minutes. Remove the streusel from the oven and allow to cool on the baking sheet.
Add a small handful of streusel to the bottom of each bowl, top with a few scoops of ice cream and top with another handful of streusel.