Pumpkin & Tomato Soup with Grilled Cheese Sandwiches 

Fall is in full swing, and this is the settle-down-and-cozy-up-under-a-blanket dish you didn’t even know you needed! This is from my book Rustic Joyful Food: Meant to Share. Enjoy!

Pumpkin & Tomato Soup with Grilled Cheese Sandwiches 

Serves 4-6 people 

Prep time 20 minutes 

Cook time 30-40 minutes 

Soup

1 chopped onion, red or white

2-3 ribs of celery, rough chopped 

1 carrot, rough chopped

2 fresh tomatoes, sliced 

5-8 cloves of garlic 

2 tablespoons olive oil 

1/4 teaspoon red pepper flakes (optional) 

2 teaspoons onion powder 

Salt and pepper to taste 

1 15-ounce can OR 2 cups fresh pumpkin cubes 

1 27-ounce can whole peeled tomatoes in sauce or juice 

4 cups low sodium chicken stock 

1/2 cup basil, rough chopped 

1/2 cup heavy cream plus more for a drizzled finish 

Garnish 

1/4 cup olive oil 

1 cup heavy cream 

1 pound cooked bacon 

1/2-1 cup fresh torn basil

Grilled cheese sandwiches (Makes 3 sandwiches) 

8 slices sourdough 

1/2 cup soft butter 

4 cups shredded cheddar cheese 

1.     In a large soup pot sauté the veggies plus the garlic in the olive oil 3-5 minutes over medium-high heat. Parts of the vegetables should begin to brown at the edges.  

2.     Add the onion powder, pepper flakes (optional), and salt and pepper. Toast 1 minute in the oil.

3.     Add the pumpkin, tomatoes, and chicken stock, then stir to combine. Reduce heat to medium and simmer 30 minutes or until the vegetables are tender and falling apart. 

4.     Turn the heat off and add the basil. Using an immersion blender, blend the soup until it’s nice and creamy.  

5.     Next, make the grilled cheese sandwiches! Spread butter liberally on one side of each slice of bread. 

6.     Lay 2 slices of bread in a skillet, butter side down, over medium-high heat. 

7.     Add 1 cup shredded cheddar to each bread slice, then top with buttered bread, butter side up.

8.     Fry 3-4 minutes per side, adjusting the heat so as not to burn the sandwiches. 

9.     Repeat this process with the other 2 sandwiches. These are VERY cheesy, so feel free to use less cheese if you prefer. 

10. Ladle the soup into bowls, drizzle with olive oil, and swirl cream on top. Add crumbled bacon and fresh basil. Serve with grilled cheese sandwiches!