Preheat the oven to 450°
Slice the acorn squash in half and scoop out all of the seeds and guts
Place the squash skin side down on a foiled baking sheet. Sprink salt, pepper, and a little olive oil over the squash and bake for 30-40 minutes or until the squash is soft on the inside
While the squash is cooking, in a pan over medium head add your pork and cook until the pork reaches 145°, drain, and set aside
In a large pan over medium heat add the butter and let melt
Once butter it melted add the garlic, onion, celery, thyme, parsley, and sage. Let cook 3-5 minutes or until the onion is transulent.
Slowly pour the chicken broth into the pan with the garlic, onion, and celery and bring to a simmer. Add some salt and pepper to taste
Add the stale sourdough bread pieces to the pan and mix well so the croutons are absorbing the chicken broth
Stir in the cooked port and most of the pomegranates (save a little to add as a garnish at the end). Remove the sage leaves from the mixture.
Remove the squash from the oven and stuff with the pomegranate pork stuffing, place back into the oven and bake for 10-15 minutes
Remove from oven, garnish with a little thyme and pomegranates to serve!