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Preheat oven to 350 degrees
Place squash in a roasting pan. Toss to coat with 2tbspns of olive oil and bake until tender and slightly carmelized (25-30 minutes). Heat butter in a large stock-pot over medium high heat until hot. Add onions and saute until tender and browned. Add garlic, roasted squash and wine and cook over high heat until reduced by one-half. Add stock and bring to a boil. Reduce heat to low and simmer 15 minutes. Meanwhile, heat remaining tsp of olive oil in a a saute pan over medium high heat. Add sausage and cook until it is browned. Drain fat. Strain squash mixture througha fine sieve. Puree solids and return puree to stockpot. Stir in remaining ingredients and heat thoroughly. Ladle into individual soup bowls and garnish with homeade croutons.