Preheat oven to 350 degrees F. Halve squash lengthwise and remove seeds. Place squash halves, cut side down, in a shallow baking dish. Bake, uncovered, for 55 to 60 minutes or until tender. Cool squash completely. Scoop squash pulp from shell using a spoon. Using a potato masher or fork, mash pulp until smooth. Or place squash in a food processor bowl; cover and process until smooth. Measure 1 cup pulp into a small bowl; stir in milk. Set aside. Use remaining squash pulp for Squash Butter (should have about 2/3 cup).
Meanwhile, grease the bottom and 1/2 inch up the sides of a 9x5x3-inch loaf pan; set aside. In a medium bowl combine flour, baking soda, the 1/2 teaspoon salt, and black pepper; set aside. In a large mixing bowl beat together cream cheese and butter with an electric mixer on medium speed for 30 seconds. Add brown sugar; beat until well combined. Beat in eggs.
Alternately add flour mixture and squash mixture to brown sugar mixture, beating on low speed after each addition just until combined. Spoon batter into prepared pan. In a small bowl stir together the maple sugar, sage, and 1/4 teaspoon salt. Sprinkle over batter in pan. Bake for 55 to 60 minutes or until a wooden toothpick inserted near center comes out clean. Cool in pan on wire rack for 10 minutes. Remove from pan. Cool completely on wire rack. Wrap and store overnight before slicing. Serve with Squash Butter. Makes 16 servings.
In a small saucepan combine mashed squash pulp, brown sugar, honey, lemon juice, and ground sage. Bring to boiling, stirring to mix well; reduce heat. Cook, uncovered, over medium-low heat for 40 minutes or until very thick, stirring often. Remove from heat; cool. Serve with Potimarron Bread. To store, place in an airtight container and chill up to 1 month. Makes 2/3 cup.