Place squash flesh side down on a baking sheet and roast for about 1 hour, turn squash over half way through.
Remove from oven and let cool.
Place a large pot or dutch oven over medium-high heat. Add coconut oil to the pot.
Once coconut oil is melted, add onions and cook for 3-4 minutes until softened.
Add garlic and ginger to the pot and cook another minute.
Add the cinnamon and red pepper flakes, stir to coat then add the kabocha flesh (it should come right out of the skin after roasting) to the pot.
Add the chicken broth and milk and stir to combine.
Bring the mixture to a simmer and cook for about 5-7 minutes until heated through.
Use an immersion blender or process in a blender in batches until smooth.
Ladle the soup into serving bowls then drizzle with the tart cherry concentrate (about 1 tablespoon per bowl) and top with a pinch of the chopped pecans and cherries.