Preheat oven to 400°F (200°C). On a baking sheet, toss the butternut squash cubes with 1 tbsp olive oil, salt, and pepper. Roast for 20-25 minutes until tender and lightly caramelized. Transfer half of the roasted squash to a blender with a splash of vegetable broth and blend until smooth. Set aside the purée and the remaining squash cubes.

In a large skillet or Dutch oven, heat the remaining 1 tbsp of olive oil over medium heat. Add the minced shallot and cook for 2-3 minutes until softened. Add the minced garlic and chopped sage and cook for 1 more minute until fragrant.

Deglaze the pan with the white wine, simmering for a minute. Add the uncooked orzo and toast for 1-2 minutes, stirring. Pour in the warm vegetable broth, bring to a simmer, then cover and cook on medium-low for 8-10 minutes, or until al dente, stirring occasionally.

Stir the butternut squash purée, heavy cream, and grated Parmesan cheese into the cooked orzo. Continue stirring until the sauce is creamy and the cheese has melted. Gently fold in the reserved roasted squash cubes.

Season to taste with salt and pepper. Serve immediately, garnished with extra Parmesan cheese, toasted pepitas, and fresh sage if desired.