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Creamy Roasted Tomato Soup & Grilled Cheese

5 from 4 votes
Prep Time15 minutes
Cook Time30 minutes
Total Time45 minutes
Servings: 4

Ingredients

For the Creamy Roasted Tomato Soup:

  • 3 lbs. Tomatoes quartered
  • 1 Yellow Onion chopped
  • 1 head Garlic or 6 cloves
  • 1 Honeynut Squash seeds removed
  • 3 tbsp. Olive Oil separated
  • 1 tsp. Salt & Black Pepper
  • 1/4 cup Fresh Basil Leaves
  • 2 tbsp. Unsalted Butter
  • 2 tbsp. Flour
  • 1 tbsp. Honey
  • 1 quart Vegetable Stock or chicken bone broth
  • Optional 1/4 cup Heavy Cream

For the Grilled Cheese:

  • Freshly Grated Medium Cheddar
  • Sliced Havarti
  • Sourdough Bread Loaf or pullman loaf-style bread
  • Unsalted Butter

Instructions

For the Creamy Roasted Tomato Soup:

  • Preheat oven to 450F.
  • Add the quartered tomatoes, chopped yellow onion, halved honey nut squash, and garlic. If using the whole garlic head, slice the very top off to reveal the cloves inside. Drizzle generously with 2 tablespoons olive oil, then season with salt and black pepper.
  • Roast for 15-20 minutes, until tomatoes are juicy and vegetables tender.
  • Let cool to room temperature, then transfer all vegetables and juices to a high speed blender. If using the whole garlic head, squeeze the cloves out of their skins. Use a spoon to scoop out the honey cut squash from its exterior. Add the basil. Blend until very smooth.
  • In a large soup pot over medium high heat, combine the butter, remaining 1 tablespoon olive oil and flour. Mix until a roux forms, about 1 minute. Stir in the honey.
  • Add the chicken broth, and as you stir, bring to a boil. Reduce heat to medium, then add the blended tomatoes. Stir until well-combined.
  • Bring to a boil once more, then simmer for 5-10 minutes. If desired, stir in the heavy cream.

For the Grilled Cheese:

  • Butter the outside pieces of your bread slices, then one slice butter-side down on a skillet over medium low heat. (You can also use a generous drizzle of olive oil directly in the skillet to replace the butter.) Add a generous serving of freshly grated medium cheddar and slice of havarti to the slice. Sandwich with the remaining buttered slice. Cook for 3-4 minutes, then flip to cook an additional 2-3 minutes, until golden brown on both sides and cheese is melted. Enjoy warm!
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