Caramelized Butternut Squash with Gorgonzola and Cranberry-Balsamic Glaze

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Caramelized Butternut Squash with Gorgonzola and Cranberry-Balsamic Glaze is everything fall should taste like—sweet, savory, tangy, and warm. I first made it on a chilly October night for a family dinner, and it’s been a returning favorite ever since.

The butternut cubes roast until golden and tender, while the cranberries soak up a sticky balsamic glaze that adds just the right zing. Then comes the Gorgonzola—bold, creamy, and melting slightly into every bite. It’s the kind of dish that feels indulgent yet simple, making it perfect for holidays or quiet nights in.

Whether it’s your first time making roasted squash or your fiftieth, you’re in for a comforting, flavor-packed experience.

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Why This Recipe Is Special

What makes Caramelized Butternut Squash with Gorgonzola and Cranberry-Balsamic Glaze stand out isn’t just the way it tastes—it’s how it feels. Every forkful brings together sweet, savory, and tangy elements in perfect harmony. The natural sugars in butternut squash caramelize beautifully in the oven, especially when brushed with just a hint of honey or maple syrup. It’s warm, golden, and nearly melts in your mouth.

Then comes the sharp contrast: creamy crumbles of Gorgonzola cheese melting slightly into the roasted squash. The funkiness of the cheese cuts through the sweetness like a whisper of sophistication. Add in dried cranberries and a homemade balsamic glaze—sticky, tart, and rich—and the flavor profile suddenly deepens. It’s not just a side dish anymore; it becomes the star.

I love how Caramelized Butternut Squash with Gorgonzola and Cranberry-Balsamic Glaze adapts to so many occasions. Serve it at Thanksgiving, use it as a meatless main, or pair it with something hearty. It’s surprisingly flexible, especially when nestled beside something like Cranberry-Glazed Roasted Butternut Squash & Brussels Sprouts with Feta or even a creamy dish like Honey-Glazed Acorn Squash with Brie Cheese and Cranberry Drizzle.

This recipe also wins on texture—tender squash, chewy cranberries, melty Gorgonzola, and (if you choose) toasted walnuts for a satisfying crunch. Every bite offers contrast, depth, and comfort. And best of all? It comes together easily, with just a handful of ingredients and no special tools.

If you’re looking for something both comforting and bold, Caramelized Butternut Squash with Gorgonzola and Cranberry-Balsamic Glaze might just become your new cold-weather obsession.

Ingredients & Preparation 

What You’ll Need for This Cozy Dish

The magic of Caramelized Butternut Squash with Gorgonzola and Cranberry-Balsamic Glaze lies in its simplicity. Every ingredient plays a role in layering flavor, texture, and color.

Here’s what you’ll need:

Ingredient Amount Notes
Butternut squash (peeled & cubed) 1 medium (~900 g) Cut into 1-inch cubes
Olive oil 2 tbsp (30 mL) For roasting
Honey or maple syrup 1 tbsp (15 mL) For caramelization
Sea salt ½ tsp (3 g) Balances sweetness
Black pepper ¼ tsp (1 g) Adds warmth
Dried cranberries ½ cup (60 g) Slightly tart, chewy texture
Balsamic vinegar ¼ cup (60 mL) Reduced into a sticky glaze
Gorgonzola cheese (crumbled) 100 g Adds bold, creamy flavor
Toasted walnuts (optional) 2 tbsp (20 g) For crunch and nutty finish

You can swap Gorgonzola with blue cheese or even feta if you prefer something milder. Maple syrup offers a deeper sweetness than honey, so choose based on your taste.

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Caramelized Butternut Squash with Gorgonzola and Cranberry-Balsamic Glaze

Caramelized Butternut Squash with Gorgonzola and Cranberry-Balsamic Glaze


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  • Author: Sylvia
  • Total Time: 40
  • Yield: 4 servings

Description

Caramelized Butternut Squash with Gorgonzola and Cranberry-Balsamic Glaze is a cozy, elegant fall side dish featuring sweet roasted squash, creamy cheese, and tangy glaze.


Ingredients

• 1 medium butternut squash (about 900 g), peeled, seeded, and cubed

• 2 tablespoons olive oil

• 1 tablespoon honey or maple syrup

• 1/2 teaspoon sea salt

• 1/4 teaspoon black pepper

• 1/2 cup dried cranberries

• 1/4 cup balsamic vinegar

• 100 g Gorgonzola cheese, crumbled

• 2 tablespoons toasted walnuts (optional)


Instructions

1. Preheat oven to 400°F (200°C) and line a baking sheet with parchment.

2. Toss cubed squash with olive oil, honey, salt, and pepper.

3. Spread squash evenly on the baking sheet and roast for 25–30 minutes, flipping halfway.

4. In a small saucepan, simmer balsamic vinegar and cranberries for 5–7 minutes until thickened.

5. Transfer roasted squash to a serving dish.

6. Drizzle the cranberry-balsamic glaze over the squash.

7. Top with crumbled Gorgonzola and toasted walnuts if using.

8. Serve warm.

Notes

– Use maple syrup for a deeper, earthier sweetness.

– Blue cheese or feta can replace Gorgonzola for a milder flavor.

– This dish is naturally gluten-free—just verify your balsamic vinegar label.

– Best served fresh, but can be made ahead and assembled just before serving.

– Store leftovers in an airtight container for up to 4 days.

  • Prep Time: 10
  • Cook Time: 30
  • Method: Roasted
  • Cuisine: American
Final dish of caramelized butternut squash with cranberry glaze
A stunning dish to serve at any fall gathering

Tools & Easy Prep Tips

No fancy tools needed—just a good baking sheet, a small saucepan, and a sharp knife. Roasting squash can be tricky if your knife is dull, so be careful slicing. I recommend peeling the squash before cutting, then halving lengthwise to scoop out seeds easily.

The glaze is quick: simmer balsamic vinegar until thickened, then stir in cranberries. Let it cool slightly before drizzling.

If you’ve made cozy sides like Creamy Ricotta & Spinach Stuffed Sweet Potatoes or the irresistible Sweet Potato Rounds with Blue Cheese & Cranberries, you’ll find this recipe follows a similar flow—just a handful of ingredients transformed in the oven.

Roasting time is about 25–30 minutes, and everything can be prepped in advance, making it ideal for entertaining or weeknight cooking.

Cooking Instructions & Tips 

Step-by-Step Instructions for Caramelized Butternut Squash with Gorgonzola and Cranberry-Balsamic Glaze

Step 1 – Preheat & Prep
Preheat your oven to 400°F (200°C). Line a baking sheet with parchment paper or foil. Toss the butternut squash cubes with olive oil, sea salt, black pepper, and honey or maple syrup until evenly coated.

Step 2 – Roast the Squash
Spread the squash cubes in a single layer on the sheet. Roast for 25–30 minutes, flipping halfway through, until caramelized and fork-tender.

Step 3 – Make the Balsamic-Cranberry Glaze
While the squash roasts, pour the balsamic vinegar into a small saucepan. Bring to a gentle simmer over medium heat. Stir in the cranberries and let it reduce for 5–7 minutes, until thickened slightly. Set aside.

Step 4 – Assemble and Finish
Once the squash is golden, transfer it to a serving platter. Drizzle generously with the cranberry-balsamic glaze. Sprinkle over crumbled Gorgonzola and, if using, toasted walnuts. Serve warm.

Tips for Perfect Results Every Time

  • Don’t overcrowd the pan. Give the squash space to roast, not steam. Use two sheets if needed.

  • Let the glaze cool slightly. A warm—but not hot—glaze clings beautifully to the squash and doesn’t melt the cheese too quickly.

You’ll find this method straightforward, much like preparing Mini Phyllo Cups with Brie, Pecans & Cranberry Drizzle—all about timing and layering flavor.

For a touch of indulgence, try pairing the dish with Baked Brie in Bread Bowl with Cranberry Sauce. The creamy, gooey textures complement each other beautifully, especially for holiday spreads.

Serving, Storing & Pairing 

What to Serve with Caramelized Butternut Squash with Gorgonzola and Cranberry-Balsamic Glaze

The beauty of Caramelized Butternut Squash with Gorgonzola and Cranberry-Balsamic Glaze is how easily it fits into a variety of meals. It’s elegant enough for the holiday table, yet cozy and casual enough to sit next to a simple roast chicken or even a grain bowl.

For entertaining, I love pairing it with soft cheeses, rustic breads, and fresh herbs. The bold Gorgonzola plays well with other creamy textures, especially when served alongside a warm appetizer like Baked Brie in Bread Bowl with Cranberry Sauce and Thyme. That combination brings out the richness of the glaze and the tart pop of cranberries.

If you’re building a vegetarian meal, this dish shines next to vibrant seasonal recipes like Mini Phyllo Cups with Brie, Pecans, and Cranberry Drizzle. The flavors echo each other while still offering variety.

Whether you’re hosting a holiday dinner or simply want a cozy Sunday side, this recipe adds visual appeal, rich flavor, and just the right amount of decadence.

How to Store and Reheat

Got leftovers? You’re in luck—this dish stores beautifully.

  • To refrigerate: Transfer cooled squash and toppings to an airtight container. Store up to 4 days.

  • To freeze: While squash freezes well, the texture of Gorgonzola may change. Freeze the roasted squash and glaze separately for best results (up to 2 months).

  • To reheat: Warm in a 350°F (175°C) oven for 10–15 minutes. Add fresh Gorgonzola and walnuts after reheating to keep textures ideal.

You can also enjoy it cold, tossed into a salad or grain bowl. Just drizzle a touch more glaze and add a handful of greens or cooked farro for an easy next-day lunch.

It’s one of those recipes that feels like a treat—whether served fresh or warmed up later.

Caramelized Butternut Squash with Gorgonzola and Cranberry-Balsamic Glaze served on a wooden board
Richly caramelized butternut squash topped with tangy Gorgonzola and cranberry-balsamic glaze

Frequently Asked Questions (FAQ)

Can I make this recipe ahead of time?

Yes! Roast the squash and make the balsamic glaze up to 2 days in advance. Store separately in the fridge, then reheat and assemble with Gorgonzola just before serving.

What’s a good substitute for Gorgonzola?

Try blue cheese, feta, or goat cheese for a milder option. Each still gives a creamy tang that balances the sweet squash and glaze.

Can I use fresh cranberries instead of dried?

Yes, but dried cranberries add chewy contrast. If using fresh, cook them briefly in olive oil and a little sugar to soften the tartness.

Is this dish gluten-free?

Yes—Caramelized Butternut Squash with Gorgonzola and Cranberry-Balsamic Glaze is naturally gluten-free. Just check your balsamic vinegar label to be safe.

How do I toast the walnuts?

Toast in a dry skillet over medium heat for 2–3 minutes, stirring until fragrant. Let cool before topping the dish.

Can I serve this cold?

Absolutely! It’s great chilled or at room temp, especially over greens or grains like quinoa or farro.

Can this be a vegetarian main dish?

Yes. Add chickpeas, lentils, or a grain like couscous to turn it into a hearty, meatless meal.

Can I double the recipe?

Easily. Use two baking sheets so the squash roasts evenly. The glaze can be made in one larger batch.

Conclusion

There’s something undeniably comforting about a dish that brings both elegance and ease to the table—and Caramelized Butternut Squash with Gorgonzola and Cranberry-Balsamic Glaze does just that. From the sweet roasted squash to the tangy balsamic glaze and creamy Gorgonzola crumbles, every bite is a celebration of seasonal flavor.

It’s the kind of recipe that draws people in—whether you’re serving it alongside a classic Warm Baked Brie with Figs and Pecans or setting it next to something simple like Maple Garlic Butter Sweet Potatoes with Toasted Pecans. It always earns a second helping—and sometimes, even a request for the recipe.

So whether you’re planning a holiday menu or just craving a cozy night at home, this dish is one you’ll want to return to again and again.

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