Roasted Butternut Squash & Cranberry Medley is a beautiful mix of sweet and tangy flavors, with tender roasted squash and bright, juicy cranberries. The butternut squash caramelizes in the oven, bringing out its natural sweetness, while the cranberries add a pop of color and a lovely tartness that balances everything perfectly.
I love making this dish because it feels like a little celebration of fall in every bite. The roasting brings out such a cozy, warm feel, and the cranberries keep it fresh and lively. When I’m in a rush, I toss the squash and cranberries together with a drizzle of olive oil and a pinch of salt and spice—it’s that easy but so satisfying.
This medley is one of my go-to sides for holiday dinners or anytime I want something simple but special. It pairs wonderfully with roasted chicken or even just some crusty bread. Plus, it’s great for meal prep because it holds up well and reheats nicely without losing its flavor or texture.
Key Ingredients & Substitutions
Butternut Squash: This is the star of the dish. Choose a firm squash with bright skin for the best flavor. If you can’t find butternut, sweet potatoes or pumpkin also work well.
Cranberries: Fresh cranberries add tartness and color. Frozen are fine too—just don’t thaw them before roasting. You can swap with dried cranberries, but add them after roasting to avoid burning.
Olive Oil: It helps the squash roast nicely and adds flavor. If you prefer, use avocado or melted coconut oil for a different twist.
Herbs & Spices: Thyme, rosemary, and cinnamon create a cozy, warm flavor combo. Fresh herbs work great if you have them on hand—use twice the amount of dried to fresh.
Maple Syrup or Honey: Optional, but I like adding a touch for caramelized sweetness. If you want to keep this sugar-free, skip it; the squash is sweet on its own.
How Do You Get Perfectly Roasted Butternut Squash Cubes?
Roasting squash evenly can be tricky because of its size and moisture. Here’s how I do it:
- Cut the squash into uniform 1-inch cubes for even cooking.
- Don’t overcrowd the pan—spread cubes in a single layer so air circulates and they roast instead of steam.
- Toss squash with olive oil well; this helps them brown and crisp on the outside.
- Roast at 400°F to get tender cubes with a golden edge in about 30-35 minutes, stirring halfway through.
- If using maple syrup, add it early so it can caramelize but watch closely to prevent burning.
Following these tips will give you tender, caramelized squash with a great texture that pairs beautifully with the tart cranberries.
Equipment You’ll Need
- baking sheet – I like using a rimmed one to hold everything in place while roasting.
- Parchment paper or silicone baking mat – keeps the squash from sticking and makes cleanup easier.
- Large mixing bowl – for tossing the squash and cranberries with oil and spices.
- Sharp knife and cutting board – for peeling and cutting the squash safely.
- Measuring spoons and cups – to keep your spices and liquids just right.
- Spatula or large spoon – for tossing the squash and cranberries during roasting.
Flavor Variations & Add-Ins
- Swap cranberries for chopped apples or pears for a different sweet-tart flavor.
- Add nuts like pecans or walnuts after roasting for crunch and extra flavor.
- Mix in a pinch of ground ginger or nutmeg to enhance the warm spices.
- Use fresh herbs like sage or parsley on top before serving for a bright, fresh note.
Roasted Butternut Squash & Cranberry Medley
Ingredients You’ll Need:
- 1 medium butternut squash (about 2 pounds), peeled, seeded, and cut into 1-inch cubes
- 1 cup fresh or frozen cranberries
- 2 tablespoons olive oil
- 1 tablespoon maple syrup or honey (optional, for slight sweetness)
- 1 teaspoon dried thyme
- 1 teaspoon dried rosemary, crushed
- ½ teaspoon ground cinnamon
- Salt and freshly ground black pepper, to taste
- Fresh rosemary sprig, for garnish (optional)
How Much Time Will You Need?
This dish takes about 10 minutes of prep time to peel and cube the squash and season everything. Then you’ll roast it for roughly 30-35 minutes, tossing halfway, to get tender, caramelized squash and softened cranberries. In total, plan for about 40-45 minutes from start to serving.
Step-by-Step Instructions:
1. Prepare the Oven and Squash:
Preheat your oven to 400°F (200°C). Line a baking sheet with parchment paper or lightly grease it to prevent sticking. Peel and cut your butternut squash into 1-inch cubes, making sure they’re roughly the same size for even cooking.
2. Season the Squash:
Put the squash cubes in a large mixing bowl. Drizzle with olive oil and maple syrup or honey, if using. Sprinkle in the dried thyme, crushed rosemary, ground cinnamon, salt, and pepper. Toss everything together well so the squash is evenly coated with the oil and spices.
3. Roast the Squash:
Spread the seasoned squash in a single layer on the prepared baking sheet. Place it in the oven and roast for about 20 minutes. This step helps start the caramelization process.
4. Add the Cranberries and Finish Roasting:
Take the baking sheet out of the oven and gently toss the squash. Scatter the fresh or frozen cranberries evenly over the squash. Return the pan to the oven and roast for another 10-15 minutes until the squash is tender and golden, and the cranberries have softened but still keep their shape.
5. Serve and Garnish:
Remove the tray from the oven and transfer the medley to a serving dish. If you like, tuck a sprig of fresh rosemary on top for a lovely aromatic touch. Serve warm alongside your favorite roasted meat or grain bowl for a colorful, tasty side.
Can I Use Frozen Cranberries Instead of Fresh?
Yes! Frozen cranberries work perfectly without thawing—just toss them directly onto the squash partway through roasting. This helps retain their shape and adds a nice burst of tartness.
Can I Make This Dish Ahead of Time?
Absolutely! Roast the squash and cranberries as directed, then store leftovers in an airtight container in the fridge for up to 3 days. Reheat gently in the oven or microwave before serving.
How Can I Adjust the Sweetness?
If you prefer a less sweet dish, skip the maple syrup or honey. For extra sweetness, add a bit more maple syrup or sprinkle some brown sugar before roasting—just watch carefully to avoid burning.
What Can I Substitute for Butternut Squash?
Sweet potatoes or pumpkin cubes are great alternatives. They roast similarly and bring a comparable sweetness and texture to the dish.