When the Fall chill hits right around Rosh Hashanah and Succos time, we tend to forget that we complained about the heat the whole summer and run for our coziest sweaters – well, I do anyway. Nothing says fall to me like a soup that warms you from the inside out! The greatest thing about the food on Rosh Hashana is that it is always sweet. It reminds us as we sit together as a family, that we made it through another year again, BH! It only adds to the beauty of the Chag that the simanim are timed perfectly with fall produce. Gorgeous apples to dip in honey, perfectly ripe interesting gourds, and beautiful, lush pomegranates just beginning to ripen. This soup combines the cinnamon-y warmth of fall, utilizes the beautiful fall produce, and captures the sweet flavor of the new year.
Heat the oven to 425 degrees Fahrenheit and arrange a rack in the middle.
Line a baking sheet with aluminum foil. Place the squash pieces cut-side up on the baking sheet. Melt one tablespoon of the vegan butter and brush all of it over the tops and insides of the squash halves (alternatively, you can rub it on evenly with your fingers). Season generously with salt, pepper, and pumpkin pie spice. Roast until knife tender, about 50 minutes to one hour.
Meanwhile, peel, core, and cut the apple and pear into medium dice. Cut the onion into medium dice. Melt one tablespoon of vegan butter in a large saucepan or Dutch oven over medium heat. Add the apple, pear, onion, and eight sage leaves, season with salt and pepper, and cook, stirring occasionally, until softened, about seven minutes. Remove the pan from the heat and set aside.
When the squash is ready, set the baking sheet on a wire rack until the squash is cool enough to handle. Using a large spoon, scoop the flesh into the saucepan with the sautéed apples, pears, and onions; discard the skins.
Add the broth, water, and measured salt and pepper, stir to combine, and bring to a boil over medium-high heat. Reduce the heat to medium low and simmer, stirring occasionally and breaking up any large pieces of squash, until the flavors meld, about 15 minutes. Remove the pan from the heat and stir in the wine, soy milk, and remaining two tablespoons of vegan butter. Stir until the butter melts.
Using a blender, purée the soup in batches until smooth, removing the small cap (the pour lid) from the blender lid and covering the space with a kitchen towel (this allows steam to escape and prevents the blender lid from popping off). Alternatively, use an immersion blender. Taste and season with salt and pepper as needed.
Pumpkin pie spice is a combination of different spices that can be found in a local supermarket. If you are having trouble finding it, make your own! Just mix two tablespoons ground cinnamon, one tablespoon ground ginger, two teaspoons ground nutmeg, one teaspoon lemon zest, 1/2 teaspoon allspice, and 1/2 teaspoon ground cloves and store in a sealed container for up to three months.
Preheat the oven to 350 degrees Fahrenheit.
In a large bowl, whisk together the honey, oil, salt, pepper, and sage leaves. Add the breadcrumbs and toss together with the oil-honey mixture until coated. Lay in a single layer on a baking sheet.
Bake for 10-20 minutes, tossing midway so that all sides get nicely browned. Cool to room temperature and sprinkle a few croutons on top of each bowl of soup. Garnish with chopped sage leaves.