Stuffing Stuffed Pumpkins

Name: Stuffing Stuffed Pumpkins
Ingredients: 6 c. (9 oz.) rustic bread, cut into 1/2-inch cubes; 4 tbsp. unsalted butter; 8 oz. cremini mushrooms, thinly sliced; 1 medium yellow onion, chopped; 1 celery stalk, thinly sliced; 4 garlic cloves, minced; 1 bunch kale, stemmed and torn into pieces; 1 tbsp. chopped fresh thyme leaves; 1/3 c. white wine; 1 c. chicken broth; 1 c. chopped pecans; 2 large eggs; 1/4 c. dried cranberries; 1 shredded monterey jack; 2 small sugar pumpkins (about 2 lb. each); 1 small butternut squash, peeled and chopped (5 cups); 2 tbsp. extra-virgin olive oil; Kosher salt; Freshly ground black pepper