Preheat oven to 375. Cut acorn squashes in half and small slice on edges to sit upright independently. Scoop out seeds. Prick with fork. Lightly brush with olive oil and lightly sprinkle with sea salt. Roast in oven facing downwards in baking dish for about 30-45 minutes based on thickness of squash. Should be very soft.
Prepare quinoa – ½ cup quinoa, rinsed with 1 cup of water. Bring to a boil and simmer until water absorbed. About 25 minutes. Set aside.
In a large sauté pan, cook pancetta until desired doneness (slightly crispy). Set aside on paper towel. Sauté one diced onion on medium heat in a bit of olive oil until brown and softening. The more color you can develop (without burning, of course) the better. Slow-cooked onions add so much flavor!
Once the onion has cooked 10-15 minutes, add the diced apple and chopped sage and cook until soft. Add the cranberries and the cooked quinoa, and turn heat down to low.
Whisk olive oil, vinegar, cinnamon, and salt together into a dressing. Pour dressing over quinoa mixture, add cooked pancetta, and continue to stir over low heat.
Once the acorn squash has cooked, flip them right side up and fill the squash with the quinoa mixture, add a small trickle of balsamic vinegar if desired and sprinkle with cheese if desired.
Bake 10-15 additional minutes, until the tops of the quinoa is golden and starting to get crispy.