This grilled cheese with caramelized butternut squash and kale is an incredibly satisfying sandwich filled with gooey melted goat cheese, sweet roasted squash, and kale.
Grilled Cheese with Caramelized Butternut Squash and Kale
- Quick Glance
- Quick Glance
- 20 M
- 45 M
- Serves 2
Preheat the oven to 350°F (180°C).
On a rimmed baking sheet, arrange the squash in a single layer. Drizzle with the oil and sprinkle with the spices and then use your hands to rub the oil and spices all over the squash slices. Give them a good sprinkling of salt and pepper.
Roast the squash, turning occasionally, until soft, sticky, and golden brown, at least 15 minutes.
Meanwhile, in a large bowl, stir together the kale or arugula and lemon juice. This will help soften the leaves slightly.
Butter 1 side of each bread slice and then turn the slices over. Layer the goat cheese, kale, and squash on 2 of the slices of bread. Top with the other slices, butter side up, and press down.
Place a nonstick skillet over medium heat to warm. Carefully place the sandwiches in the pan. Cook, flipping once, until golden brown, about 4 minutes per side. (Alternatively, you can set the sandwiches on a baking sheet and pop them into the 350°F (180°C) oven until golden brown, 8 to 10 minutes.)
Recipe Testers' Reviews
A hit! “Gorgeous” and “It was a beast,” said one of my tasters as he made his way through with pleasure. For starters, the butternut squash prepared with these spices could be served by itself. The combination of olive oil, dried chile flakes, ground nutmeg, paprika, salt, and pepper was so good I took a piece of bread to the roasting pan to scoop up the extra oil and spices that didn’t adhere to the squash.
My handful of baby kale turned out to be too skimpy in proportion to the other ingredients. “I don't understand the point of the kale,” said another of my tasters. The sandwich was terrific as made, but I would amend this to at least 2 handfuls as the color really made a difference, in addition to enhancing the overall taste of the sandwich.
I was traveling when I made this and I found the most beautiful 100% rye seeded with pumpkin seeds, sunflower seeds, and caraway seeds. It wasn’t the rye I had anticipated using but it worked perfectly for this sandwich and I would seek it out again, though I am certain a softer less dense seeded rye would also yield a tasty sandwich. That being said, one of my tasters noted that the bread really made a difference to his satisfaction.
It was clear to me that I would not be able to stack the ingredients and then flip the sandwich over, so I opted for the pop-it-in-the-oven approach, even before I assessed the messiness of the melted cheese. Hence there was no butter involved in my sandwich.
Because I did not attempt to make a sandwich that could be placed in a pan and flipped over, I made my sandwiches open-faced, and there were therefore 4 of them. I layered the goat cheese, kale, and squash as directed, but just did not place a slice of bread atop.
Three hungry eaters each ate one of these sandwiches and despite their enjoyment, no one needed a second in terms of being satisfied. Note that we ate these with fork and knife—a steak knife was perfect to carve through the layers.
Going back to my tasters for a moment, they felt the open-faced approach was how it should definitely be served. Additional thoughts included making smaller slices of bread or rounds of bread and stacking them up, perhaps with the assistance of a toothpick, and serving them as an appetizer with a splash of balsamic atop and, if serving for brunch, for example, adding an egg atop as well. This would also be wonderful alongside a bowl of soup in the winter, especially next to a roaring fire in the fireplace.
This seemingly unusual combination of sandwich fillings turned out to be a fantastic grilled cheese. The combination of toasty rye, tangy goat cheese, sweet and spicy squash, and lemony kale was a flavor explosion! Who needs meat?
I think the amount of cheese in each sandwich is a pure preference thing and easy enough to adjust if you prefer more. Also, 1/2 a squash made WAY more than could fit into 2 sandwiches. My half a squash yielded about 15 slices and I only need 3 per sandwich.