Preheat oven to 400°F.
Prepare the acorn squash by slicing them in half lengthwise. Place the squash halves on a roasting pan and drizzle with olive oil. Par-cook the squash in the oven for 20–30 minutes, or until you can prick the squash with a paring knife but it’s still slightly firm. Set aside.
Meanwhile, prepare the filling. Over medium-high heat, add the butter to a sauté pan. Add onions, mushrooms and herbs. Cook until the onions begin to soften and the mushrooms are tender. Deglaze the pan with the ¼ cup of red wine. Simmer for 3–5 minutes, until most of the liquid has evaporated. Add the pork and the apples. Cook until the pork is browned through. Remove the filling mixture from the heat.
Once the filling is cooked, fill each squash half with the mixture. Place the stuffed squash in the oven and roast for 30 more minutes. Remove from the oven. Top with toasted walnuts and pomegranate seeds.