5 bacon slices, chopped
1 cup coarsely grated extra-sharp cheddar cheese plus 1/2 cup 1/4-inch cubes extra-sharp cheddar cheese (about 6 ounces total)
1/2 cup finely chopped moist dried pears (about 3 1/2 ounces)
1/3 cup walnuts, toasted, chopped
1 tablespoon minced fresh sage
1 3/4 cups all purpose flour
1 tablespoon baking powder
1/2 teaspoon salt
1/4 teaspoon ground black pepper
3 large eggs
1/3 cup whole milk
1/3 cup extra-virgin olive oil
Position rack in center of oven and preheat to 350°F. Generously butter 8 1/2 x 4 1/2 x 2 1/2-inch metal loaf pan. Cook bacon in large skillet over medium heat until crisp. Transfer bacon to paper towels to drain.
Combine bacon, all cheese, dried pears, walnuts, and sage in medium bowl. Whisk flour, baking powder, salt, and black pepper in large bowl to blend. Whisk eggs, milk, and olive oil in another medium bowl to blend. Pour egg mixture over flour mixture and stir just until dry ingredients are moistened. Add bacon-cheese mixture and stir until incorporated (dough will be very sticky). Transfer dough to prepared loaf pan; spread evenly.
Bake bread until golden on top and slender knife inserted into center of bread comes out clean, about 55 minutes. Cool bread in pan 5 minutes, then turn out onto rack and cool completely. DO AHEAD Can be made 1 day ahead. Wrap in plastic, then foil, and store at room temperature.