Heaven to most kids might be tomato soup and a grilled cheese but as you get older Campbell’s and Kraft just aren’t as good as you remembered. That is why for years I have made creamy tomato soup from scratch, and this week I was looking at squash that need to be use up so I decided to pump up my basic tomato soup recipe. Creamy Tomato and Squash Soup was born.  I have to say plain squash soup that tastes like liquid pumpkin pie has never been my favorite, and I think it is because most recipes use chicken broth to make up the majority of the liquid in the soup. My Creamy Tomato and Squash Soup replaces basic broth with a jar of store bought spaghetti sauce, the richness of the soup is dramatically improved.  I can’t wait to pair the leftover soup with some grown up Havarti grilled cheese sandwiches for dinner tonight.

Creamy Tomato and Squash Soup

When making a pureed soup like this one you are in charge of how smooth the soup will be. If you like a bit of body then mix it less if you want the more of the five star restaurant liquid silk feel get out a food mill and get to work. For me I just pop it into the food processor and give it a whirl. To encourage a nice texture be sure that the squash is roasted until tender; you want it to be very soft, like mashed potatoes.

Creamy Tomato and Squash Soup

This recipe calls for cooking sherry, it’s something that I use occasionally and find its bright bite very useful in certain recipes. I think of it as a lighter version of Worcestershire sauce that can be used to add life to something dull. Soy and fresh lemon are other ingredients that I think of as flavor enhancers, which can take a dish from plain to sparkling. I think the ability to “fix” or improve a dish using these kinds of ingredients is a trick many good cooks use all the time, improving the dish that is in front of them rather than slavishly following a recipe.  If you don’t normally buy cooking sherry, I say give it a try!

Directions for how to roast garlic are below.


Creamy Tomato and Squash Soup

Course Soup
Prep Time 25 minutes
Cook Time 45 minutes
Total Time 1 hour 10 minutes
Servings 8


  • 1 large butternut or other hard squash calabasa or pumpkin
  • 2 small onions diced
  • 2 carrots diced
  • 2 ribs of celery diced
  • 1 tbs Italian spice blend
  • 1 14.5 oz can diced fire roasted tomatoes
  • 1 24 oz jar of tomato pasta sauce
  • ½ cup white wine
  • Head of roasted garlic
  • 2 cups heavy cream
  • 2 tbs cooking sherry
  • Salt & Pepper
  • Olive oil
  • Soft goat cheese to garnish


  1. Cut the squash into large chunks, drizzle with olive oil and a generous amount of salt. Place on sheet pan and roast at 375 degrees until very tender. About 30-45 minutes depending on the size of the squash. When cooked allow to cool and scoop the flesh from the peel, then roughly mash. You will need about 4 cups of mashed flesh.
  2. Sweat the celery, onion and carrot in a large pot with salt and olive oil until tender. Add in the fire roasted tomatoes with can liquid and the spices, let cook for another 5 minutes. Add the white wine and tomato sauce, allow to cook until bubbling. Add the squash, and mashed roasted garlic. Cook soup for 20 minutes on low heat or until everything is tender.
  3. Use a stick blender to puree the soup in the pot, or working in batches puree the soup in either a food processor or blender. Over very low heat add in the cream and taste. Add salt and pepper as needed and finish with the sherry.
  4. Serve with a dollop of soft goat cheese and lots of fresh black pepper.

Recipe Notes

If you don’t have cooking sherry you could use more wine or even vermouth. Be sure to taste and adjust to your pallet.

If the soup is too thick, add more wine, cream or broth to thin.

How to Roast Garlic

Course Appetizer, vegetarian


  • Garlic
  • Olive Oil
  • Cooking spray
  • Salt
  • Tin Foil


  1. Pre-heat your oven to 325. Prep the garlic by removing the lose skins and then slicing the top off.
    Slice tops off the heads
  2. Then pour olive oil into each head to fill it up, and salt liberally. Cut a large piece of tin foil and spray the inside of the foil with cooking spray to be sure the garlic will not stick.
  3. Next tightly and carefully seal up the garlic in the foil. Then place in the oven, I use my toaster oven to roast garlic most of the time so I don’t have to heat up the whole house with the big oven.
  4. Roast for 1-1.5 hours checking to be sure the garlic is slowly caramelizing and softening. You can store unused garlic in the fridge for a week at least.

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