Preheat the oven to 425°F (or 218°C).
Roast the squash: Slice each butternut squash or acorn squash in half and scoop out the seeds and gunk with a spoon. Place each squash half, cut side up, on a baking sheet and rub each with a bit of olive oil, kosher salt, and pepper. Roast acorn squash halves for 45 minutes and butternut squash halves for 50-55 minutes or until the flesh is fork tender and lightly browned.
Rinse the wild rice well.
Wild Rice, Instant Pot Method: Add the wild rice and 1 1/2 cups vegetable broth to the inner pot of the Instant Pot. Secure the lid and select the Pressure Cook/Manual setting for 25 minutes. Allow a natural pressure release and drain off any remaining liquid.
Wild Rice, Stovetop Method: Place the wild rice and 3 cups of vegetable broth in a saucepan over medium-high heat. Bring to a boil, then turn the heat down and cover. Simmer for 40-45 minutes, or until the kernels have burst open. Drain off any remaining liquid.
Make the wild rice salad: Heat the 1 tablespoon olive oil in a skillet. Once hot, add the shallots and cook until they are starting to soften, about 4 minutes. Add the garlic for 1-2 minutes, stirring frequently, until golden.
Add the shredded kale and season to taste with salt and pepper, stirring for 1-2 minutes or until the kale is starting to soften.
Turn off the heat and transfer the vegetable mixture to a large bowl. Add the cooked and drained wild rice, along with the pine nuts, chopped parsley, chopped basil, dried cranberries, pomegranate seeds, orange zest, orange juice, and 1 tablespoon extra virgin olive oil. Toss well to combine and incorporate the flavors. Season to taste with salt and pepper.
Stuff each squash cavity with the wild rice salad. Drizzle each half with tahini. Serve with additional chopped parsley on top, if desired.1. NOTE: you can also scoop out flesh from the roasted butternut squash to create a more hollowed out boat. That way, you can add more of the wild rice filling into each boat.