Butternut Squash Soup with a Cheddar-Gruyere Grilled Cheese
The first night it feels like fall. Roasted butternut blended silky-smooth, brightened with orange and a little maple, and the real event - a cheddar-and-gruyere grilled cheese with a swipe of fig jam, cut into soldiers for dunking.
- Prep
- 15 min
- Cook
- 25 min
- Total
- 40 min
- Serves
- 4
- Method
- One Pot
Roast the squash until the edges caramelize before it goes in the pot. Boiling it just makes it watery and flat; roasting concentrates the sugars, and that caramelized sweetness is the whole difference between a great squash soup and baby food.
What actually matters here
- Roast the squash for caramelized, not boiled and flat.
- Blend it fully smooth and season boldly.
- Griddle the grilled cheese low and slow so the cheese melts before the bread burns.
Ingredients
Serves 4.
Soup
- 1butternut squash (about 2 to 3 lb)
- 1onion
- 3garlic cloves
- 3 cupsbroth
Finish
- 1orange, juiced
- 1 tbspmaple
- cream and black pepper
Grilled Cheese
- sharp cheddar and gruyere
- good bread
- butter
- fig jam
Before you start
- Heat the oven to 425F. Peel the butternut squash, scoop out the seeds, and cut into 1-inch cubes so they roast evenly. Peel and halve the onion. Toss both on a sheet pan with olive oil, salt and pepper.
Method
- Roast the squash and onion at 425F for about 25 minutes, until soft and caramelized brown at the edges. Roasting is the whole difference, it concentrates the sugars; boiling would leave it watery and flat.
- Move it to a pot with the garlic and enough broth to nearly cover, and simmer a few minutes. Blend fully smooth, either with an immersion blender right in the pot, or in a countertop blender in batches, filling it only halfway and holding the lid down with a towel (hot soup expands and can blow the lid off).
- Stir in the orange juice and maple, then season BOLDLY with salt and pepper, tasting as you go. A squash soup needs more salt than you'd think to come alive. Loosen with a splash more broth if it's too thick.
- Make the grilled cheese: butter the outsides of the bread, fill with cheddar, gruyere and a thin swipe of fig jam, and griddle over medium-LOW 3 to 4 minutes a side, until deep golden and fully molten inside. Low and slow melts the cheese before the bread burns.
- Swirl a little cream into each bowl, crack over black pepper, and cut the grilled cheese into soldiers for dunking.
How you know it is right
- The soup is silky and pourable, deeply orange and well-seasoned; the grilled cheese crisp outside and molten in.
How to serve it
The grilled cheese IS the side; a handful of greens if you want.
If you want it simpler
- Bagged pre-cut squash; canned pure butternut or pumpkin in a pinch; coconut milk instead of cream to make it vegan.
Roast the squash, blend it smooth, season it bold, and dunk the grilled cheese. That is the night.
This dish came from the SEASON plan for September 7 - 13, 2026, alongside nine other dinners and one shopping list.
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Written and tested by Chef Michael Rossi, who has spent thirty years in professional kitchens including Napa Rose, THE RANCH, The Masters at Augusta National, and The Beach Club. Every SEASON recipe is one he has cooked on a real line before it reaches a home kitchen.