Place bacon in the skillet and cook until crispy, set aside leaving grease in the pan.
Add 2 tablespoons olive oil to the bacon grease and add the shallot to the skillet. Cook for 1 minute.
Add the brussels sprouts and pumpkin, season with salt and pepper, stir and let cook for 7-10 minutes until softened and starting to brown on the bottom. Toss and cook another 3 minutes.
Add the apples, cranberries and sage, mix and cook for another 3 minutes.
Turn the heat off, add the vinegar and toss to combine.