In a large bowl combine flour, 1/2 teaspoon Italian seasoning, 1/4 teaspoon salt, and 1/4 teaspoon pepper. In another bowl whisk together eggs and 1 cup milk until well blended. Add wet ingredients to dry ingredients and whisk until smooth. Cover and let sit for 30 minutes.
Preheat and lightly grease a large skillet. Pour 1/4 cup of the batter into the middle of the skillet, then tilt the skillet in a circular motion to get the batter to spread into a large, thin disk. Allow to cook 45 seconds to a minute until golden and the top of the crepe begins to look more dry. Flip, and cook another 30-45 seconds on the other side until golden. Repeat with remaining batter.
Melt butter in a large pan over medium heat. Add butternut squash, garlic, remaining Italian seasoning, remaining salt, remaining pepper, and sauté until squash begins to brown. Add water, cover, and cook for 7-8 minutes until squash is tender. Drain any excess liquid and transfer squash to a bowl. Add goat cheese to bowl and smash squash with a fork until blended with cheese.
In a small sauce pan combine cranberry sauce and orange juice and stir over medium-high heat until blended and hot throughout (about 2-3 minutes). Remove from heat.
Assemble crepes by filling each crepe with squash and cheese mix, and pear slices. Fold crepes in half and spread cranberry sauce over the top half. Sprinkle walnuts and herbs over the top and serve with remaining 8-ounce glass of milk.