Step 1In a wide sauté pan, heat the pumpkin seeds over medium heat just until they begin to make a popping sound. Sprinkle over a pinch of salt, and continue toasting the seeds while shaking the pan (be careful to keep the seeds moving, or they will burn on the bottom of the pan). When the seeds are lightly toasted and fragrant, remove from heat. Grind them in a food processor and place in a small bowl, tossing with the pumpkin seed oil and salt to taste to form a "pesto." This makes about two-thirds cup pesto.
Step 1Peel and seed the squash, and cut it into 1-inch cubes.
Step 2Heat a large, heavy-bottomed pot over medium-high heat until hot. Add the butter and oil, and stir until the butter melts. Stir in the squash and season with 1½ teaspoons salt and one-fourth teaspoon nutmeg. Reduce the heat to medium and cover the pot to cook the squash. Remove the lid every 5 to 10 minutes, stirring the squash to cook it evenly.
Step 3Once the squash is softened and begins to break down, after about 15 minutes, add the diced onion and garlic cloves. Cover with the lid again and continue to cook for about 10 minutes to soften the aromatics and marry the flavors.
Step 4Remove the lid and increase the heat to high while stirring the squash. Stir in the sage, rosemary and thyme, then add the wine, scraping the bottom of the pot to loosen any flavor and stirring constantly to prevent burning. When the wine is mostly evaporated, stir in enough broth just to cover the squash mixture by 2 inches. Bring the soup to a boil, then reduce the heat and simmer, covered, for 20 minutes to marry the flavors. Stir in the tomatoes and juice, and continue to simmer, covered, for an additional 10 minutes.
Step 5Strain the herbs from the soup. Blend the soup to a purée using an immersion blender or in batches using a stand blender. Taste the soup, seasoning additionally with one-half teaspoon salt, one-fourth teaspoon nutmeg and one-fourth teaspoon cayenne pepper, or as desired. This makes a generous 2 quarts soup. For a creamier soup, add a little cream before blending the soup. Serve the soup garnished with the pesto and whipped cream if desired.