The Perfect Fall Grilled Cheese Sandwich
The second I saw this recipe in my Food Network magazine, I knew I had to try it. This sandwich really is the perfect fall grilled cheese. It starts with some hearty wheat bread. Next comes a layer of cheddar cheese. Thinly sliced butternut squash gets roasted with some maple syrup and chili powder for the next layer. As if that doesn’t sound good enough, a big heaping pile of balsalmic caramelized onions get stacked on along with some slivered almonds for crunch. And last but not least, another layer of cheddar cheese. Seriously, tell me that doesn’t sound amazing.
Hubby and I have made these sandwiches more times that I care to count in the last few weeks since I first made one. I don’t actually measure the ingredients precisely, I just kind of stack the sandwiches together in a ratio that sounds good.
One Year Ago: Banana Cinnamon Chip Blondies, Apple Slab, Cappuccino Toffee Brownie Cookies, and Graham Cracker Chewy Bars
Two Years Ago: Pumpkin Spice Cookies
Three Years Ago: Shipping Cupcakes in a Jar, and Chocolate Marshmallow Bars
Four Years Ago: Black Bean Cilantro Turkey Burgers
The Perfect Fall Grilled Cheese Sandwich
Yield: Serves 4
Ingredients:
3 Tbsp unsalted butter, plus more for the bread
1/2 butternut squash, peeled, seeded and sliced 1/4 inch thick
2 Tbsp maple syrup
1/2 tsp chili powder
Kosher salt and freshly ground pepper
1 sweet onion, thinly sliced
1/4 cup balsamic vinegar
1 tsp sugar
8 slices country wheat bread
1 pound manchego or cheddar cheese, thinly sliced
1 cup sliced almonds, toasted
Directions:
Preheat the oven to 425 degrees F. Line a baking sheet with parchment paper or foil. Melt 2 tablespoons butter. In a large bowl, toss the squash with the melted butter, maple syrup, chili powder, and salt and pepper to taste. Spread in one layer on the prepared baking sheet. Roast until golden and soft, about 20-30 minutes. Set aside and let cool.
Meanwhile, melt 1 tablespoon butter in a medium skillet over medium-low heat. Add the onion and toss to coat. Cook, without stirring, until the onion begins to develop a deep brown color, 10 to 15 minutes. Stir and add the balsamic vinegar, sugar, and salt and pepper to taste. Cook, stirring, until the onion mixture thickens and develops an intense sweetness, about 15 more minutes.
Butter 1 slice of bread. On the unbuttered side, add the ingredients in this order from the ground up: cheese, squash, caramelized onion, sliced almonds and more cheese. Close with another buttered bread slice, buttered side up. Repeat with the remaining ingredients to make 3 more sandwiches.
Heat a heavy griddle or flat pan over medium heat. Lightly cook each sandwich, in batches if necessary, until the cheese starts to melt, 3 to 4 minutes per side.
Recipe from Food Network
I am Jen the Beantown Baker. Engineer by day and baking maven by night. Hubby serves as my #1 fan and official taste tester. We got hitched back in 2006. Barefoot. In the sand. With the waves crashing behind us. It was one of the best decisions we’ve ever made. 
I have been loving Butternut Squash more than ever this season, myself! Your pictures are lovely, and making me hungry!
I LOVE butternut squash… especially when roasted until slightly crisp on the outside. Your caramelized version looks great – I will need to add a touch of brown sugar and butter next time I make it.
YUM!!! I started my butternut squash kick this weekend- this looks amazing!
I have a butternut squash from my CSA that I’m dying to cut into. I have a question though, how does one peel a butternut squash?
Melissa – I like to use a Y-shaped vegetable peeler to peel the skin off. You could do it with a knife, but I would be worried about cutting myself.
Sounds like a fabulous way to prepare those squash. I’ll have to remember this for if we have another bumper crop next year!
Hi Jen, nice seeing you again yesterday. I usually roast my butternut squash with brown sugar too but I can’t believe I never thought of adding butter! I usually omit the salt and pepper because I like it very dessert-like, so I add cinnamon too 🙂
what a great blog!
here is so many inspirations,
have a nice time,
Paula
I love butternut squash too. It’s definitely delicious with just a bit of brown sugar. Sometimes I go a bit overboard and roast it with a whole lot of butter, brown, sugar, and maple syrup.
This looks amazing! I love bn squash. I just made a fantastic soup, and now I want to carmelize it!
This is such a simple way to cook butternut squash and yet SO delicious! I’m loving your butternut squash blog posts!