Preheat the oven to 400F. Line a baking sheet with parchment paper.
Rub the insides of each delicata squash half with olive oil then sprinkle spices (garlic powder, paprika, nutmeg, salt, and pepper) over each one. Place on the prepared baking sheet (insides side down) the bake in the oven until soft, about 20-30 minutes.
Meanwhile, cook the frozen bag of rice and veggies according to the package instructions. Once cooked, pour contents into a medium sized bowl. Add dried cranberries and pecans to the bowl then mix well.
Also meanwhile, whisk together vinaigrette ingredients in a small measuring cup.
Once squash are cooked, remove them from the oven. Flip each squash over then fill with rice mixture. Finally, top with shredded cheddar then place back in the oven to bake for an additional 5-10 minutes or until the cheese is melted.
Remove squash from the oven again, drizzle maple dijon vinaigrette over top then serve!