Preheat the oven to 425 degrees F.
On a sheet pan, toss the butternut squash with 1 tablespoon olive oil, 1/2 teaspoon salt and 1/4 teaspoon black pepper spread it into a single layer. Roast the squash for 20 minutes until it starts to lightly brown at the edges.
Add the broccoli to the pan, tossing it with the squash. Arrange the vegetables, so they are in a single layer. Continue roasting for 10-12 minutes until the squash is tender and more browned and the broccoli is bright green and darker at the edges.
Warm 1 tablespoon olive oil in a large sauté pan or skillet over medium high heat. Add the garlic, shallots and remaining salt and pepper, cooking until fragrant, about 30 seconds. Stir in the orzo and toast it for 1 minute.
Pour in 2 cups vegetable broth. Bring to a boil and reduce the heat and simmer uncovered. Cook the orzo, stirring frequently, until al dente, about 7-9 minutes. If the liquid has been absorbed and the orzo is not tender, add more broth by the 1/4 cup.
Stir in the roasted butternut squash and broccoli, parmesan and parsley.