Roasted Tomato Soup with Pesto and Grilled Cheese Croutons

You know those big containers of grape tomatoes you can get at Costco?  Well, I’m a sucker for them. Problem is I can never seem to use them up fast enough before they start to wrinkle unless I have a recipe already planned for them.  And that’s what happened this last time I purchased them.  So I tossed them in the oven to roast while I figured out what to make out of them.  I thought some kind of soup would be good and ended up with this delicious Roasted Tomato Soup with Pesto and Grilled Cheese Croutons!

Roasted Tomato Soup with Pesto and Grilled Cheese Croutons

I sort of winged it with this recipe, but was quite pleased with the end result.  First I sliced the tomatoes in half and placed them on a cookie sheet, drizzled them with olive oil, salt and pepper and threw in some fennel seeds for good measure.  I also tossed in some garlic cloves as well (roasted garlic is so yummy).

Roasted Tomato Soup with Pesto and Grilled Cheese Croutons

After about 20 minutes I took them out of the oven since they all turned to mush and added them to a pot that had some diced onions, carrot and celery sautéing.  Next I added some chicken stock and let it simmer for a bit.   After a while I blended it all up and added a couple heaping tablespoons of pesto, and voila…Roasted Tomato Soup.  And, because I love to dunk a grilled cheese sandwich in my tomato soup, I cut one up into bite sized pieces and put them on top like croutons!

Roasted Tomato Soup with Pesto
  • 1 lg. container (or 2 smaller ones) grape tomatoes
  • 6 cloves garlic, whole, skins left on
  • Olive oil, enough to coat the tomatoes and sauté vegetables
  • salt & pepper
  • 1 tsp. fennel seeds
  • 1 onion, diced
  • 1 celery stalk, diced
  • 1 carrot, diced
  • 1 tsp. dried basil
  • 1 Tbls. tomato paste
  • 2½ C. chicken stock
  • 1 tsp. sugar
  • ½ C. half & half
  • 2 Tbls. Pesto (homemade or storebought)
  • Garnish: dollop of pesto and grilled cheese sandwich cut into bite sized pieces
  1. Preheat oven to 400 degrees.
  2. Slice tomatoes in half and lay flat on baking tray. Add garlic, fennel, salt and pepper and toss with olive oil to coat. Roast for about 20 minutes.
  3. Meanwhile, in soup pot, sauté onions, celery, carrot in about 2 tablespoons of olive oil. Add dried basil and a little salt and pepper to season as the vegetables cook.
  4. Remove tomatoes from oven. Peel skins off garlic and add garlic to soup pot with the tomatoes and all the juice on the baking tray. Add chicken broth, sugar and tomato paste. Stir, cover and simmer for about 15-20 minutes.
  5. Puree soup with immersion blender, then add half and half and pesto. Let simmer a few more minutes, then serve.
  6. Garnish with an extra dollop of pesto and a grilled cheese sandwich cut into bite sized pieces
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