Heat remaining 2 tablespoons olive oil in a large skillet over medium heat. Add the garlic, celery, and onion then cook, stirring often, until soft and translucent (about 5-7 minutes). Next, stir in the rosemary, sage, and thyme and cook about 1 minute (or until they release their fragrance).
Beat eggs together in a large bowl then add the dried out bread cubes. Mix to combine and coat the bread in egg. Next, add the celery onion mixture and roasted butternut squash to the bowl with the bread cubes and toss to combine.
Transfer mixture to a large casserole pan. Pour vegetable stock over mixture, cover with foil, then bake at 350F for 20 minutes. After 20 minutes, uncover the pan, stir the mixture, and bake until the stuffing is steaming hot and golden, but not dry (10-20 minutes more – a toothpick inserted in the middle should come out clean). Enjoy!!