Step 1: Preheat your oven to 400°F (200°C) and line a large baking sheet with parchment paper.
Step 2: Slice the acorn squash in half from stem to tip and scoop out the seeds. Brush the flesh with 1 tablespoon of olive oil and the maple syrup, then season with salt and pepper.
Step 3: Place the squash cut-side down on the baking sheet and roast for 30-35 minutes, or until the flesh is tender and the edges are starting to brown.
Step 4: While the squash is roasting, combine the wild rice blend and vegetable broth in a medium saucepan. Bring to a boil, then reduce heat to low, cover, and simmer for 40-45 minutes (or according to package directions) until tender.
Step 5: In a large skillet, heat the remaining 1 tablespoon of olive oil over medium heat. Add the onion and sauté for 5 minutes until soft. Add the garlic, sage, and thyme, and cook for another 1-2 minutes until fragrant.
Step 6: Stir the chopped kale into the skillet and cook until wilted. Fold in the cooked wild rice, dried cranberries, and toasted pecans. Season the mixture with extra salt and pepper to taste.
Step 7: Flip the roasted squash halves over and fill each cavity generously with the wild rice pilaf. Return to the oven for 10 minutes to heat through. Garnish with extra herbs and serve warm.