Preheat oven to 350F.
Heat a large sauté pan over medium heat until oil is hot but not smoking. Add Hubbard squash, and season with salt and pepper. Roast for 8-10 minutes, or until just tender.
Heat a second large sauté pan over medium heat until oil is hot but not smoking. Add apple cubes, and season with salt and pepper. Roast for 4-5 minutes, until tender but not mushy.
Set squash and apple aside to cool.
When squash and apple are cool, season with sea salt, black pepper, extra virgin olive oil, and lemon juice. Add the chiffonade of red kale and toss gently. In a separate bowl, combine the radish, apple matchsticks, and fresh parsley leaf. Season with salt and pepper.
Mound the cubed Hubbard squash and apple mixture in the center of cool plates. Top with the salad of julienned radish and apple. Finish with aceto and serve.