Caramelized Butternut Squash topped with Blue Cheese and Cranberry Maple Glaze.

caramelized-butternut-squash-with-blue-cheese-and-cranberry-maple-glaze

caramelized-butternut-squash-with-blue-cheese-and-cranberry-maple-glaze sounds a little extra, and honestly, it is in the best way. Maybe you’re hosting a fall dinner or you just want a side dish that makes people stop talking mid-bite. I’ve made this for small weeknight meals and big holiday tables, and it always disappears. The squash gets sweet and tender, the maple glaze is glossy and tangy, and the blue cheese melts into little pockets of salty magic. If you’re not sure about blue cheese, trust me, it ties the whole thing together. Plus, it’s easy enough for a regular Tuesday.

caramelized-butternut-squash-with-blue-cheese-and-cranberry-maple-glaze

Why You Will Love This Recipe

Let me paint the picture. You pull a sheet pan from the oven and the roasted butternut squash has these caramelized edges that almost crunch when your fork hits them. You drizzle over a warm cranberry maple glaze, scatter blue cheese, and maybe a handful of toasted nuts if you want to flex a little. It tastes like fall without trying too hard.

Here’s the thing I love most. The recipe hits every note: sweet, salty, tangy, creamy, and a little herby. It’s great hot, warm, or even room temp, so it’s ideal for gatherings. And yes, it looks restaurant-level pretty with barely any effort. This is the kind of side that can stand next to a roast chicken or shine with a simple salad. It’s also flexible. If you’re worried about strong flavors, use a mellow blue cheese or swap in goat cheese. If you want heat, add a pinch of chili flakes to the glaze. When I need an easy win, I lean on caramelized-butternut-squash-with-blue-cheese-and-cranberry-maple-glaze.

If you like planning a full menu, try pairing this with something green and crisp like roasted Brussels sprouts. I’ve got a version I love right here: Roasted Brussels Sprouts with Balsamic.

“I brought this to Friendsgiving last year and people were literally asking for the pan. Not the recipe, the pan. I doubled it this year and still nothing was left.”

caramelized-butternut-squash-with-blue-cheese-and-cranberry-maple-glaze

Ingredients and Substitutions

Butternut basics

  • Butternut squash: Fresh is best. Aim for a medium squash, around 2 to 2.5 pounds, peeled and cubed into 1 inch pieces.
  • Olive oil: Helps achieve those caramelized edges. Avocado oil works too.
  • Salt and pepper: Don’t be shy. Season the squash well before roasting.

Glaze and flavor

  • Maple syrup: Real maple syrup gives a clean, deep sweetness. Honey can be used, but maple truly shines here.
  • Dried cranberries: They plump up in the warm glaze and bring a bright pop. You can use fresh cranberries if you simmer them longer with a little extra maple.
  • Apple cider vinegar: Just a splash balances sweetness. Lemon juice works in a pinch.
  • Butter: For a silky finish in the glaze. Use vegan butter if needed.
  • Fresh thyme: Earthy and gentle. Rosemary or sage also works nicely.

Cheese and extras

  • Blue cheese: Choose a creamy kind like Gorgonzola dolce for mild flavor, or a sharper one if you love bold. If you’re not into blue, goat cheese or feta still give that salty tang.
  • Optional crunch: Toasted pecans, walnuts, or pepitas add texture. I love pecans here.

Shopping shortcut tip: you can buy pre-cut squash if peeling feels like a hassle. I often do this on busy weeks and it still tastes fantastic.

Want another cozy side to round out the meal? Take a peek at my Garlic Mashed Potatoes for something creamy and simple.

caramelized-butternut-squash-with-blue-cheese-and-cranberry-maple-glaze

How to Make Maple Roasted Squash

This is straightforward, but a few small moves make a big difference. You’ll roast the squash first to get that deep caramel color. Then you’ll finish with a quick stovetop glaze and sprinkle the cheese at the end so it softens without melting into oblivion.

  1. Prep the squash: Heat your oven to 425°F. Toss the squash cubes with olive oil, salt, and pepper. Spread them in a single layer on a big sheet pan. Keep space between pieces so they roast instead of steam.
  2. Roast for color: Cook 20 minutes, flip, then roast another 10 to 15 minutes until the edges are golden and the centers are tender. Look for deep browning on a few sides. That equals flavor.
  3. Make the glaze: In a small pan, melt butter over low heat. Add maple syrup and apple cider vinegar. Stir in dried cranberries and simmer for 1 to 2 minutes, just until the cranberries start to plump and the glaze thickens slightly. Add a pinch of salt and a few thyme leaves.
  4. Combine and finish: Transfer hot squash to a serving platter. Spoon the warm cranberry maple glaze over the top. Scatter blue cheese and more thyme. If using nuts, add them now for crunch.
  5. Taste and tweak: If it needs more brightness, add a tiny splash of vinegar or a squeeze of lemon. If you like heat, dot with a pinch of red pepper flakes.

At this point, caramelized-butternut-squash-with-blue-cheese-and-cranberry-maple-glaze is ready to serve. It holds well on the table for a bit, which is a lifesaver when you’re juggling the rest of dinner.

Tips and Tricks

Cut even cubes for consistent browning. Try to keep pieces around 1 inch so they roast before drying out.

Use a hot oven. 425°F is the sweet spot for caramelized edges without burning the sugars in the maple later.

Dry the squash if it seems wet after peeling. A quick pat with a towel helps those edges crisp up.

Glaze timing matters. Pour glaze over the squash while it’s still hot so the flavors soak in and the blue cheese softens just right.

Season at each step. Salt the squash before roasting, then taste again after glazing. A tiny pinch of salt at the end wakes everything up.

Make it ahead. Roast the squash earlier in the day. Rewarm and glaze right before serving. The cheese should go on last for the best texture.

If you’re building a holiday menu, you might like this cozy side too: Classic Herb Stuffing.

How to Reheat It

Oven method

Spread leftovers on a sheet pan and warm at 350°F for 8 to 10 minutes. If you kept the blue cheese off the first time, add it after reheating so it softens nicely. You can splash in a spoonful of water and cover with foil for a few minutes if the squash looks dry, then uncover to finish so the edges perk up.

Skillet or microwave

Skillet: Add a little oil to a pan and warm the squash over medium heat until hot. Microwave: Heat in short bursts, stirring once. Either way, refresh with a drizzle of maple and a few new thyme leaves if you want. The cheese might melt a bit more, but it still tastes great.

Good news: This dish tastes lovely warm or room temp, so reheating is usually low stress. If you plan to prep ahead for guests, roast the squash, store the glaze separately, then reheat and assemble right before serving. That keeps textures at their best.

Common Questions

Can I peel and cut the squash in advance?
Yes. Store cubes in an airtight container in the fridge for up to 2 days. Pat dry before roasting so they caramelize well.

What if I don’t like blue cheese?
Use goat cheese or feta. You still get that salty tang without the classic blue flavor. The spirit of caramelized-butternut-squash-with-blue-cheese-and-cranberry-maple-glaze stays intact.

Can I use frozen squash?
You can, but it might not caramelize as well. Roast at a high heat and give it space. Expect softer texture, but it’s still tasty.

How do I keep the glaze from being too sweet?
Add a splash more vinegar or a squeeze of lemon. Salt helps balance too, so taste before serving.

What protein pairs well with this?
Roast chicken, pork tenderloin, or seared salmon are all excellent. For a vegetarian main, try it with a hearty grain bowl and some toasted chickpeas.

By the way, if you enjoy planning balanced meals, you might like this simple guide to easy weeknight mains: Sheet Pan Chicken Thighs.

Ready to make it tonight

Here’s the bottom line. With simple steps and a handful of pantry staples, you can make a side dish that tastes like a cozy fall hug. caramelized-butternut-squash-with-blue-cheese-and-cranberry-maple-glaze delivers sweet, tangy, creamy, and crunchy all in one bite. It looks special, but the effort is minimal. Give it a try and let me know how it goes. I’m betting you’ll be making it again next week.

Maple Roasted Squash

This easy recipe for caramelized butternut squash features a tangy cranberry maple glaze and creamy blue cheese, making it an ideal side dish for fall gatherings.
Prep Time 15 minutes
Cook Time 35 minutes
Total Time 50 minutes
Servings: 6 servings
Course: Side Dish, Vegetarian
Cuisine: American, Fall
Calories: 250

Ingredients
  

Butternut basics
  • 2 pounds Butternut squash, peeled and cubed into 1 inch pieces Fresh is best; aim for medium squash.
  • 2 tablespoons Olive oil Helps achieve those caramelized edges. Avocado oil works too.
  • to taste Salt and pepper Season the squash well before roasting.
Glaze and flavor
  • 1/2 cup Maple syrup Real syrup gives a clean sweetness. Honey can be used but maple shines here.
  • 1/2 cup Dried cranberries Can use fresh cranberries if simmered longer with extra maple.
  • 1 tablespoon Apple cider vinegar Balances sweetness; lemon juice works in a pinch.
  • 2 tablespoons Butter Use vegan butter if needed for a silky glaze.
  • 1 teaspoon Fresh thyme Earthy and gentle; rosemary or sage also works.
Cheese and extras
  • 4 ounces Blue cheese Choose creamy Gorgonzola dolce for mild flavor, or sharper if loved.
  • 1/2 cup Optional crunch: Toasted pecans, walnuts, or pepitas Adds texture; pecans are recommended.

Method
 

Preparation
  1. Heat your oven to 425°F.
  2. Toss the squash cubes with olive oil, salt, and pepper.
  3. Spread them in a single layer on a large sheet pan.
Roasting
  1. Cook for 20 minutes, flip, and roast another 10 to 15 minutes until golden.
  2. Look for deep browning on a few sides for flavor.
Making the Glaze
  1. In a small pan, melt butter over low heat.
  2. Add maple syrup and apple cider vinegar.
  3. Stir in dried cranberries and simmer for 1 to 2 minutes until they plump.
  4. Add a pinch of salt and a few thyme leaves.
Finishing
  1. Transfer hot squash to a serving platter.
  2. Spoon the warm cranberry maple glaze over it.
  3. Scatter blue cheese, more thyme, and optional nuts on top.
  4. Taste and tweak with more vinegar or lemon juice as needed.

Notes

Cut even cubes for consistent browning. Roast ahead of time and glaze before serving. Holds well at room temperature.

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