Step 1: Preheat your oven to 400°F (200°C). Line a large baking sheet with parchment paper for easy cleanup.
Step 2: Slice the acorn squashes in half from stem to point. Use a spoon to scoop out the seeds and stringy bits. Brush the cut sides with 1 tablespoon of olive oil and season with salt and pepper.
Step 3: Place the squash halves cut-side down on the prepared baking sheet. Roast for 25-30 minutes, or until the flesh is tender when pierced with a fork. Flip them over and set aside.
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 the rice is tender and liquid is absorbed.
Step 5: In a large skillet, heat the remaining 1 tablespoon of olive oil over medium heat. Add the onion and celery, sautéing for 5-7 minutes until soft. Stir in the garlic, thyme, and sage, cooking for another minute until fragrant.
Step 6: Fluff the cooked rice with a fork and add it to the skillet with the vegetables. Stir in the dried cranberries and toasted pecans. Season the pilaf with salt and pepper to taste.
Step 7: Scoop generous portions of the rice pilaf into the roasted squash cavities. Return the stuffed squash to the oven for 10 minutes to heat everything through and slightly crisp the top of the rice.
Step 8: Remove from the oven and garnish with extra fresh herbs or a drizzle of balsamic glaze if desired. Serve hot.