1 large butternut squash, seeded and cut into 6 to 8 pieces (Or, get two packages of peeled and chunked butternut squash from the produce department.)
4 medium potatoes, scrubbed and halved
2 large onions, peeled and quartered
Olive oil or olive oil spray
2 quarts chicken stock
½ cup milk
1 teaspoon brown sugar
2 to 4 tablespoons Worcestershire sauce
2 to 4 dashes of Tabasco
1/8 teaspoon Stubb’s Liquid Smoke
Kosher salt and freshly ground pepper
Preheat oven to 350°F. Line a large sheet pan with heavy duty aluminum foil and oil lightly. Place all the veggies on pan, and be sure to put squash skin-side down. Spray oil on top of veggies and liberally salt and pepper. Roast for about 1½ hours.
On the stovetop, heat 1 quart of the chicken stock in a large pot. When the veggies are done roasting, use a spoon to scoop the cooked squash away from the skin, and add the flesh and other veggies to the pot. Top off the chicken stock so it covers the veggies. Keep any remaining chicken stock for “as needed.”
Simmer the vegetables over medium-low heat for 20 to 30 minutes, or until veggies are very tender. Working in small batches, ladle equal portions of roasted veggies and their liquid into a blender. Be sure to place a towel over the lid of the blender, so when the steam releases you don’t get burned. Blend on low, then medium, then high speed for about 1 minute. Pour blended soup batches into a large mixing bowl. Repeat this process until all batches are done, and return all the soup to the original pot. Stir in milk, brown sugar, Worcestershire sauce, Tabasco, and liquid smoke; season with salt and pepper to taste.
The soup should be creamy and smooth, not watery or porridge-like. If it is too thick, add a little more chicken stock or milk.