Preheat the oven to 375 degrees F.
In a large bowl, whisk together the 1 tablespoon olive oil, maple syrup, 1 teaspoon kosher salt and 1/2 teaspoon black pepper.
Add the squash to the bowl and toss in the mixture.
Arrange the squash on the sheet pan. Roast for 30 minutes until golden brown at the edges and tender, flipping halfway through roasting.
While the squash is roasting, make the couscous. Heat 1 tablespoon olive oil in a large saucepan over medium heat. Toast the couscous until it is golden, about 5 minutes. Add the water and bring to a boil. Reduce heat to low, cover and simmer until the water is absorbed and the couscous is tender, about 10 minutes.
For the pesto, puree the garlic, parsley, 1/4 cup chopped walnuts, Parmesan, lemon juice, 1/4 teaspoon salt and 1/4 teaspoon black pepper in a food processor. Puree the mixture and while the motor is running, pour 1/3 cup olive oil through the feeder tube until the pesto is fully combined.
In a large bowl, stir the pesto into the couscous. Fold in the roasted squash, pomegranate seeds, 1/4 cup chopped walnuts and chives.