Preheat oven to 400 degrees F.
Cut each kabocha squash in half and use a spoon to remove the seeds. Cut each squash into roughly 3 inch slices (TIP: use the natrual grooves in the kabocha as a guide). Arrange the kabocha slices onto a baking tray and sprinkle with 1 tbsp olive oil. Coat with salt and pepper. Roast for 15 minutes per side, or until squash are browned.
While squash is roasting, prepare the herbed oil. Finely chop rosemary and thyme. In a small bowl, add chopped herbs, remaining olive oil, pumpkin seeds, crushed red pepper, and salt and pepper to taste. Stir to combine and set aside.
Once squash is done roasting, remove from oven and set on a serving platter. Drizzle herbed oil over the squash, then top with pomegranate seeds,