Char the peppers under the broiler. Stock in a sealed container for 15 minutes, peel, stem, seed, and coarsely chop.
Lower oven temperature to 400˚F. Chop off the tops of the squash and shave a sliver off the bottoms if needed to allow them to stand upright on their own. Scoop out the seeds and pulp, and reserve for other uses or discard.
Mix 1 Tbsp olive oil with the jam, and baste the rims and bowl of the squash. Set in a baking pan, and roast until tender - about 45-55 minutes, depending on their size.
Heat 1 Tbsp olive oil in a large skillet and add the diced onion, apple, sage and salt. Sauté until the onion and apple pieces soften, about 10 minutes.
Add the wine and simmer for 5 minutes.
Add the crumbled cornbread, Spiced Butter (recipe below), and parsley. Toss to coat, cook for 5 minutes on the stove, and pile into a buttered 8"X8" baking dish. Bake at 350˚F for 15 - 20 minutes. It's fine to share the oven with the squash as long as the squash is softening.
Scoop the stuffing into the bowls of the squash and finish with a flourish of pepitas.