Spooky Dinner Idea: Roasted Tomato Soup & Jack O’Lantern Grilled Cheese

Currently, my freezer is full of a glut of homegrown tomatoes. Tomatoes are my favorite thing to grow in the garden, and this has been my best year yet for tomatoes! I am so excited to have a freezer full so that we can have the taste of a homegrown tomato even in the depths of Winter. One of my favorite ways to use my homegrown tomatoes is in a homemade tomato soup. Since it’s Spooky Soup Season, why not pair it with an adorable jack-o’-lantern grilled cheese? Here is my recipe for homemade roasted tomato soup!

Spooky Dinner Idea: Roasted Tomato Soup & Jack-O’-Lantern Grilled Cheese

Homegrown tomatoes are so naturally sweet. They are great fresh in a salad, but when you roast them, the depth of flavor is out of this world! In fact, I think store-bought tomatoes are best when roasted. I use a combination of tomato varieties for my soups, but if you only have one type, that works just as well. For this soup I used a combination of Sungold and sweet cherry tomatoes, heirloom Oxhart tomatoes, Italian Roma, and San Marzano.

I love this recipe too because most of the other ingredients roast on the same pan with the tomatoes so the flavors all meld so well! The leeks are also homegrown as well and I loved how well they roasted for this soup. If you don’t have leeks, you can also use an onion. I think a Walla Walla Sweet would be perfect! The roasted garlic rounds out the powerhouse of flavors for this soup, and I wouldn’t make a roasted tomato soup without it!

Ingredients:

Soup:

Tomatoes (enough to fill a large baking sheet in a single layer. I used fresh and frozen)
2 Leeks chopped
6 cloves of garlic
6 sprigs of fresh thyme
1 TBSP dried oregano
4 cups of vegetable broth (I used a reduced-sodium one)
Olive oil
Salt & Pepper to taste

Grilled Cheese:

Rustic sourdough or sandwich bread of your choice
Sliced sharp cheddar
Salted butter

Method:

Preheat your oven to 425°F.
Lay out your tomatoes on your baking sheet. Cut larger tomatoes into halves or quarters. Add your chopped leeks and garlic cloves tucked in and around your tomatoes. Drizzle with olive oil and sprinkle with salt, pepper, and dried oregano. Move everything around to make sure your ingredients are well coated. Place your thyme sprigs over various spots.
Roast your ingredients for 40 minutes or until you see a bit of color and crispy bits.
While your ingredients are in the oven, place your pot or Dutch oven on the stove and preheat it about 5 minutes before the roasted ingredients come out of the oven. Also, prepare your grilled cheese. On one of the slices of bread, cut out a little jack-o-lantern face. I recommend buttering the slice of bread before carving your face. Cook in a frying pan until the cheese is melty and the bread had a lovely golden color!
Remove your ingredients from the oven and transfer them to your preheated pot or Dutch oven. Be sure to keep any liquid that has built up in the baking sheet and add that to your pot as well. Add the vegetable broth and allow the ingredients to combine for about 5 minutes.
Using an immersion blender (a regular blender works fine too, you’ll just need to transfer and likely blend in batches), and blend until smooth. Check your seasoning and adjust as needed.
Enjoy with your jack-o-lantern grilled cheese. This is such an easy dinner perfect for any Spooky Season night or even Halloween night dinner before heading out to trick or treat!