Preheat oven to 425°F. Toss together squash and oil on a rimmed baking sheet. Season with salt and pepper. Roast, turning once, until golden brown and tender, 25 to 30 minutes. Combine cranberries, maple syrup, orange juice, and rosemary in a medium saucepan. Simmer over medium heat until cranberries begin to pop, 10 to 12 minutes. Stir together goat cheese and heavy cream in a bowl until smooth. Season with salt and pepper. Serve squash topped with cheese mixture, cranberries, and pepitas.