Caramelized Butternut Squash with Gorgonzola and Cranberry-Balsamic Glaze

If fall had a flavor, I’m convinced it would taste exactly like caramelized butternut squash with gorgonzola and cranberry-balsamic glaze. It’s everything cozy, sweet, tangy, and savory all in one bite—like your favorite holiday sweater in edible form. This dish has been my go-to whenever I want to impress guests without stressing myself out. The combination of roasted squash, creamy gorgonzola, and a drizzle of sticky balsamic glaze feels downright luxurious, even though it’s secretly simple to make.

Plus, let’s talk about that cranberry-balsamic glaze for a moment. It’s like a holiday party and a fancy cheese board had a baby. Tart, jammy, glossy perfection that clings lovingly to those golden squash cubes. Pair it with the sharp, salty pop of gorgonzola and you’ve got a side dish that steals the show at Thanksgiving, Christmas, or even Tuesday night dinner.

If you’re ready to wow your people and sneak extra vegetables onto their plates, this recipe is your ticket.

Why You’ll Love This Caramelized Butternut Squash

• Sweet and savory harmony – the honey (or maple) balances the salty gorgonzola beautifully.
• Holiday-ready – it looks stunning on the table and tastes even better.
• Simple ingredients, big payoff – nothing fancy, but the flavors feel gourmet.
• Crowd-pleaser – even picky eaters are swayed by caramelized edges and tangy glaze.

This isn’t just a side dish; it’s the kind of recipe people ask you for before the plates are cleared.

Ingredients

• 1 medium butternut squash (about 2 pounds / 900 g), peeled, seeded, and cut into 1-inch cubes
• 2 tablespoons olive oil (30 mL)
• 1 tablespoon honey or maple syrup (15 mL)
• ½ teaspoon sea salt (3 g)
• ¼ teaspoon black pepper (1 g)
• ½ cup dried cranberries (60 g)
• 2 oz gorgonzola cheese, crumbled (about 55 g)
• ½ cup balsamic vinegar (120 mL)

Instructions

1. Prep the oven – Preheat to 400°F (200°C). Line a baking sheet with parchment for easy cleanup.
2. Dress the squash – In a large bowl, toss the squash cubes with olive oil, honey (or maple), salt, and black pepper until evenly coated.
3. Roast to perfection – Spread the squash on your sheet in a single layer. Roast for 25–30 minutes, flipping halfway, until caramelized on the edges and fork-tender.
4. Make the glaze – While the squash roasts, pour balsamic vinegar into a small saucepan. Simmer over medium heat until reduced by half and syrupy, about 10–12 minutes. Stir in dried cranberries and let them plump.
5. Bring it together – Transfer roasted squash to a serving platter. Drizzle with the cranberry-balsamic glaze and sprinkle with crumbled gorgonzola. Serve warm and watch it disappear

Melania’s Tips for Perfect Caramelized Butternut Squash

• Size matters – cut your squash into uniform 1-inch cubes for even roasting.
• Don’t overcrowd – give those cubes space to breathe, or they’ll steam instead of caramelize.
• Taste your balsamic – some are sweeter, others sharper; adjust honey or maple as needed.
• Make it nutty – sprinkle toasted walnuts or pecans on top for crunch.

Bake It With the Littles

If you’ve ever handed a child a spoon and said “stir this,” you know they suddenly feel like sous chefs. Kids can:

• Help measure the cranberries and drizzle the honey.
• Line up squash cubes on the tray (like building veggie Legos).
• Taste-test gorgonzola (though warning: strong cheese faces are priceless).

It’s a low-stress recipe to introduce them to real cooking.

Meal-Prep Magic

This dish is wonderfully forgiving:

• Make ahead – roast the squash up to a day in advance and reheat at 350°F before glazing.
• Glaze in advance – balsamic reduction keeps well in the fridge for up to a week.
• Leftover-friendly – store in an airtight container for 3–4 days.

It’s one of those recipes that actually tastes better after the flavors mingle overnight.

Healthier Swaps Without Losing the Magic

• Cheese – swap gorgonzola for goat cheese if you want something milder.
• Sweetener – stick with pure maple syrup for a more natural sweetness.
• Cranberries – use unsweetened dried cranberries or even fresh pomegranate seeds.
• Oil – avocado oil works beautifully if olive oil isn’t your go-to.

Leftover Remix

Because who doesn’t love giving leftovers a glow-up?

• Salad topper – toss warm cubes with spinach, toasted pecans, and a drizzle of extra glaze.
• Grain bowl – layer squash over quinoa or farro, add roasted chicken, and call it lunch.
• Flatbread magic – spread squash and gorgonzola over naan, bake until crisp, and drizzle with glaze.

Honestly, I’ve been known to eat it cold straight from the container. Zero regrets.

Gift It Like a Pro

Hosting a dinner party? Bring this dish in a pretty ceramic bowl with extra glaze on the side. Need a hostess gift? Bottle up some homemade cranberry-balsamic glaze in a cute jar with a ribbon—people will think you’re the Martha Stewart of your friend group.

FAQs

Can I use pre-cut squash?
Yes! A total time-saver, just make sure pieces are similar in size.

What if I don’t like gorgonzola?
Try feta or goat cheese for a creamier, gentler flavor.

Can I double the recipe?
Absolutely, but use two baking sheets so the squash caramelizes instead of steaming.

Is the glaze optional?
Technically yes, but you’d be missing the magic. It’s like skipping frosting on a cake.

Final Thought

This caramelized butternut squash with gorgonzola and cranberry-balsamic glaze is proof that simple ingredients can create something spectacular. It’s warm, sweet, savory, tangy, and fancy enough for the holidays yet easy enough for a weeknight. Whether you’re feeding family, friends, or just yourself (yes, solo squash feasts are a thing), this recipe has a way of making the ordinary feel special.

Print