Preheat oven to 400°F and line a rimmed baking sheet with parchment paper.
Cut the top off of the squash and slice in half lengthwise and scoop out seeds and pulp. Place skin side down on jelly roll pan.
Mix maple syrup and oil in a small bowl; brush squash with the mixture, pouring any extra into the center of the squash. Sprinkle with pepper. Roast for 1 hour or until tender. Remove from oven and let cool for 15-20 minutes.
Scoop one squash half into a blender and add 1 cup of chicken broth, process until smooth. Pour into a large saucepan and repeat with other squash half and remaining chicken broth.
Stir in the milk and season with salt & pepper. Heat over medium-low until warm.
Spoon into bowls and top with 1 tablespoon creme frâiche and sprinkle with roasted pumpkin seeds.