It’s been drizzly and disgusting around here for the past couple of days. Instead of dwelling on the weather though, I’m embracing all things warm and cozy by serving Roasted Tomato Soup with Grilled Cheese Croutons on repeat.
This updated version of classic tomato soup pairs roasted fresh tomatoes and garlic with chicken broth and dried herbs, which is scooped into bowls then topped with these adorable grilled cheese croutons.
Take it from me, it’s impossible to feel gloomy when you’re eating grilled cheese croutons!
While my brothers happily dug into bowls of heated canned/condensed tomato soup as children, I hated it with a fiery passion. This soup though, is thankfully NOT that soup! Roasted Tomato Soup has layers and layers of flavor. I know you’ll love each roasty, toasty spoonful!

Ingredients
- 3 lbs Roma tomatoes, cut in half lengthwise
- 2 Tablespoons extra virgin olive oil
- salt and pepper
- 4 garlic cloves
- 1/4 teaspoon dried thyme
- 1/4 teaspoon crushed red pepper flakes, or more or less
- 4 cups chicken broth
- 8 slices gluten free bread
- softened butter
- 8 slices cheddar cheese
Directions
- Preheat oven to 400 degrees. Lightly spray a large baking sheet with nonstick spray then line with tomato halves, cut side up. Drizzle tomatoes with extra virgin olive oil then season generously with salt and pepper. Wrap garlic cloves in foil with an extra drizzle of olive oil then place alongside tomatoes. Roast for 1 hour, or until tomatoes are golden brown and very tender. Cool slightly.
- Unwrap garlic cloves then transfer with tomatoes and their juices into a food processor or blender and pulse until tomatoes reach desired consistency (I like mine more smooth than chunky.)
- Pour mixture into a large soup pot then add dried thyme, red pepper flakes, and chicken broth then bring to a boil. Reduce heat and simmer for 20 minutes. Taste and adjust seasonings if necessary.
- Butter one side of each bread slice, then place cheese slices between the unbuttered sides. Cook in a skillet over medium heat until both sides are very crisp and cheese is melted. Remove from heat and let grilled cheese sandwiches rest for 2 minutes. Cut sandwiches into cubes then divide amongst bowls of soup. Serve immediately.
Nutrition
Nutritional values are estimates only. Please read our full nutrition information disclaimer.


















Love your blog and love those adorable grilled cheese bites. Perfect for little kids (and big kids too).
Kristin! Can you edit this post so I can save it on my ZipList???!!!! Thats the only way I grocery shop anymore :)
There you go! :)
Can’t wait to make this soup!! Do you think it would freeze well? Or could it be canned? I am the lucky recipient of 6 BOXES full of tomatoes and I’m running out of ideas and recipes!
I haven’t tried but I bet it would both freeze AND can well! :)
I have always hated canned tomato soup also, but a couple of restaurants have versions I like, so I gave this a try and it was LOOOVVVVEEE at first slurp. So yummy! I confess, I didn’t make the croutons; but it was fabulous on its own, as well as with the addition of either fresh grated Parmesan, or reheated with a few ciliegine-sized balls of fresh mozzarella tossed in. Perfection!
A hint on the beer bread: It’s fun to play around with different beers, etc. I especially love using hard cider and need to try it with pumpkin ale. Homemade beer bread is soooo easy!
I, too, look forward to this feature, and usually end up with a few new bookmarks as a result. ;)
LOVE Friday Faves!!! I always find something to eat or buy!! Bought a Scarf of the Etsy site you posted! Can’t wait to wear it!
This post has so many amazing recipes, I dn’t know where to begin! I have lots of corks and was planning to make a cork board but the trivet is a great idea too!
This looks delicious! love that it’s made from scratch! I’ll be trying it soon! also love that dress
Wonderful round-up! Thank you so much for featuring my pumpkin ravioli. :D
The soup and croutons look amazing!! I can’t wait to try it. And I think the glass candy dish is adorable. Great find!