Roasted Tomato Soup with Grilled Cheese Croutons

Though only one of my 3 kids likes tomatoes, Tomato Soup is something that all 5 of us love, so it’s in steady rotation around here. 🍅

tomato soup with grilled cheese croutons

I love to freeze perfect summer tomatoes to use for this in the winter, but the truth is, we eat tomato soup often, and my stash disappears quickly. I’m grateful for canned tomatoes for this exact reason. For my 2 kids who eat dairy, crispy, melty grilled cheese croutons are the thing that makes this meal an absolute favorite!

This soup freezes beautifully, it’s made in the blender and works well for lunch, making it an all around win! Of course, this meal can be made gluten free by using gluten free bread, and it can also be made dairy free by using dairy free cheese.

tomato soup with grilled cheese croutons lunchbox

Roasted Tomato Soup 
(serves 3-4)

2 beefsteak tomatoes, cut into chunks
1 medium red onion, sliced 
1 bell pepper, cut into chunks 
1 large clove of garlic, peeled and smashed
2 tablespoons olive oil 
3 teaspoons fresh thyme, divided
28 ounce can whole, peeled tomatoes
4 cups vegetable broth
3/4 teaspoon kosher salt, or to taste
Fresh black pepper to taste
1/2 teaspoon sugar (optional)
1/8 teaspoon cayenne (optional) 

Preheat the oven to 375 F. Line a baking sheet with parchment paper and add the chopped fresh tomatoes, onions, peppers and garlic. 
Drizzle with olive oil and sprinkle with 1 1/2 teaspoons of fresh thyme. Roast for 15-20 minutes or until the vegetables have softened and become fragrant. 
Place the roasted vegetables into a blender. 
Add the canned tomatoes (including juices), vegetable broth, remaining fresh thyme, salt and pepper. 
Blend together until smooth. Taste to determine whether more salt or pepper is needed. If you find the flavor too acidic, you can add 1/2 teaspoon of sugar. If you like it spicy, you can add cayenne.

Grilled Cheese Croutons
4 pieces of sourdough bread
4-5 ounces sharp cheddar cheese
1-2 tablespoons unsalted butter

Preheat the oven to broil.
Place sourdough slices on a baking sheet lined with foil and smear butter on one side of each slice. Place that butter side down and add cheese on top of each slice. Place into oven, open faced.
Broil for 1-2 minutes or until cheese is nice and melty.
Place two open-faced sandwiches together to create two closed-faced grilled cheese sandwiches. Let cool for about 5 minutes and cut into crouton chunks.


Tomato Tarte Tatin with Caramelized Onions

summer sungold tomatoes

summer sungold tomatoes

Brunch was always something I looked forward to at the home of our longtime family friends, Rachel and Yehuda.  Their easy company and Rachel's delicious cooking guaranteed a lovely afternoon. They entertained gracefully and graciously and Rachel had a knack for finding great recipes. She had a knowledgeable palate, and could recreate dishes that she loved in restaurants or read in print seemingly effortlessly. After coming across a recipe for Tomato Tarte Tatin from Melissa Clarke in the New York Times, she decided to give it a try. It immediately became one of her favorite dishes.

When Rachel passed away recently from ovarian cancer, the world lost one of it's kindest people. Yehuda and their children planned a celebration of her life, as a way for her loved ones to gather together and collectively remember all of the joy that Rachel brought to them over the years. Yehuda reached out to some folks, including me, and asked us to bring some of Rachel's favorite dishes with recipes that he provided. I was asked to make the Tomato Tarte Tatin. Admittedly, I was nervous. I intended to make at least one as a trial run, but time slipped away from me. 

tomato tarte tatin

On the day of the celebration, I kept thinking of something my grandma used to say about never bringing something you've never made before to a dinner party. Gulp. And because this tarte is fully contained in puff pastry, I wasn't able to taste it ahead of time. But wow did it smell delicious! It seemed promising.

When I arrived, I was struck. There were photos everywhere of Rachel (and her loved ones). They told a powerful story of a humble, wise, happy woman who traveled, spent time with people she cared about, danced, cooked, worked and raised kids. It was an eye opening way to mourn and to celebrate the life of those who we've lost. 

One other person was asked to make the tarte, so if mine was a complete fail, at least there was a different version available. The evening was bittersweet, as you can imagine, and as it turned out, my tarte was delicious! And so was the other version! Simple, yet sophisticated flavor. I wanted to eat it forever. 

Today I remember and honor Rachel's memory regularly by making this tarte. I've adapted the recipe slightly and have gotten it to a place that feels absolutely right for us. This is the dish that I bring to potluck dinners. This is the dish that I bring to brunch. This is the dish that I make for guests. And I think Rachel would be absolutely delighted by that (as would my grandma, knowing that I'm representing with a known quantity of deliciousness). It's also gorgeous to look at, particularly if you buy mixed colored tomatoes. It's an inverted dish, so once it's done cooking, you flip it over onto a serving plate and the bottom becomes the top. I got a little fancy with it a few times and used leftover puff pastry dough to decorate the top. It can be a fun reveal if you present both sides, but that's not necessary. While this tarte is best to make in summer when cherry and grape tomatoes are at their peak, it is perfect any time of year. 

unbaked tomato tarte tatin


  • 1 14-ounce package all-butter puff pastry
  • 2 tablespoons unsalted butter
  • 3 red onions, halved and thinly sliced
  • 2 tablespoons + 1 pinch sugar
  • 1 tablespoon sherry vinegar
  • 1/3 cup chopped pitted Kalamata olives
  • 2 pints cherry or grape tomatoes
  • 1 tablespoon chopped fresh thyme leaves plus extra for garnish
  • Kosher salt, to taste
  • Freshly ground black pepper, to taste
puff pastry top tomato tarte tatin


Preheat oven to 425 degrees. Thaw the puff pastry until it's still chilly, but not frozen. Unfold it and cut into a 10-inch round. Save the scraps if you want to decorate the top/bottom. Place in the refrigerator until ready to use. 

Melt butter in a large skillet over medium heat. Add onions and a pinch of sugar and cook, stirring, until onions are golden and caramelized, 20 - 25 minutes. Add 2 tablespoons water and let cook off, scraping brown bits from bottom of pan. Transfer onions to a bowl and set aside.

In a sauce pan, combine 2 tablespoons sugar and 3 tablespoons water. Cook over medium heat and swirl pan gently without stirring until sugar melts and turns amber, about 10 minutes. Add vinegar and swirl gently. Turn off heat. 

Pour the sugar, water and vinegar caramel into a 9 inch cake pan. Sprinkle olives over caramel. Add the tomatoes over olives, then spread the onions on top. Season with thyme leaves, salt and pepper. Top with puff pastry round, tucking edges into pan. Cut several long vents in top of pastry to let the steam out during the cooking process.

Bake tarte until the crust is puffed and golden, about 35 minutes. Let stand for 5-10 minutes, then run a knife around pastry to loosen it from pan, and flip tart out onto a serving platter. Garnish with thyme leaves and serve warm.

tomato tarte tatin