Preheat oven to 375° F. and line a baking sheet with parchment paper or foil.
Spray or brush the cut side of the squash halves with oil and season with salt and pepper. Place the squash on the baking sheet cut-side up and roast for 40-60 minutes depending on the size of your squash. You should be able to poke a fork or knife through the flesh easily when they are done.
While the squash roasts heat the teaspoon of olive oil in a large saucepan over medium heat. When hot, add in the shallot and sauté 2 minutes.
Add in the garlic, sage and rosemary and sauté another minute.
Add in the wild rice, lentils and water. Season with salt and pepper, stir, turn the heat up to high and bring the mixture to a boil. Once boiling, cover with a lid and reduce the heat to low. Cook until the rice and lentils are tender, approximately 35-45 minutes. (see note)
Remove the rice and lentils from the heat and fluff with a fork. Add the dressing ingredients to the saucepan and stir together until combined. Taste for seasoning. Cover with the lid to keep the filling warm until the squash is ready.
Remove the squash from the oven and let it rest for about 5 minutes before filling.
Stir the toasted pecans and pepitas into the rice/lentil mixture just before serving to keep them from getting soft. Divide the filling into the 4 squash halves. Place them on a serving dish and garnish with more dried cranberries, pepitas and pecans if desired.