Roasted Butternut Squash & Cranberry Medley is a colorful and cozy dish filled with tender, sweet squash and tangy cranberries that burst with flavor. The natural caramelization from roasting brings out the best in the squash, while the cranberries add a fresh, bright twist. It’s a great mix of soft and chewy textures, making it really satisfying and fun to eat.
I love making this medley when I want something simple but impressive. The way the squash turns golden and slightly crisp on the edges always makes me smile. Plus, the cranberries give it a pop of color that feels festive and fresh — it’s like autumn or holiday vibes all in one bowl. I like to toss in a bit of cinnamon or fresh herbs for an extra touch, depending on my mood.
This dish works perfectly as a side for a family dinner or even as a light vegetarian main when I add some toasted nuts or grains. I enjoy it warm straight from the oven, but it’s just as good the next day for lunch. Whenever I make it, everyone seems to find it hard to stop eating, which makes me think it’s a keeper for any season.
Key Ingredients & Substitutions
Butternut Squash: The star of this dish! Its natural sweetness and creamy texture shine when roasted. If butternut squash isn’t available, try acorn squash or kabocha—they roast similarly well.
Cranberries: Dried cranberries add a tart bite and chewiness. Fresh cranberries can be used if you prefer, but they are more tart and might need a dash of sweetener.
Brown Rice or Wild Rice: Cooked rice adds heartiness and balances the sweetness. Quinoa or couscous work well as alternatives if you want a different texture or quicker cooking time.
Thyme: A fresh herbal note that complements the squash and cranberries. Rosemary or sage are good substitutes, offering a cozy flavor vibe.
Maple Syrup or Honey: Optional but great for a little sweetness that rounds out the tart cranberries. You can leave it out or swap for agave or brown sugar.
How Do You Get Perfectly Roasted and Tender Butternut Squash?
Roasting the squash well is key for soft, flavorful bites. Here’s what helps me:
- Cut the squash in half and scoop out seeds for even cooking.
- Roast cut side down to get caramelized edges and smoky flavor.
- Use a hot oven (around 400°F) so the squash cooks quickly and browns without drying out.
- Check tenderness by piercing with a fork—it should slide in easily but not be mushy.
- After roasting, fill the squash with the medley and roast a bit more to blend flavors well.
Taking a little extra time here rewards you with that perfect balance of softness and caramelization that makes the dish shine.
Equipment You’ll Need
- Baking sheet – I recommend a rimmed sheet for even roasting and easy handling of the squash halves.
- Parchment paper – Keeps the squash from sticking and makes cleanup quicker.
- Sharp knife – Needed to halve and seed the squash safely.
- Cutting board – A stable surface to work on the squash.
- Large skillet – For sautéing the diced squash, cranberries, and rice mixture.
- Mixing bowls – To toss ingredients together easily.
- Measuring spoons and cups – For precise seasoning and ingredients.
Flavor Variations & Add-Ins
- Cheese topping – Sprinkle crumbled feta or goat cheese over the finished dish for added creaminess.
- Additional nuts – Swap walnuts or pecans for almonds or pistachios for variety and crunch.
- Spice it up – Add cinnamon, a pinch of cayenne, or ground ginger to the roasting or sautéing stage for warmth.
- Protein boost – Mix in cooked chickpeas, cooked turkey, or shredded chicken to make it more filling.
How to Make Roasted Butternut Squash & Cranberry Medley
Ingredients You’ll Need:
- 1 large butternut squash, halved and seeded
- 2 tbsp olive oil, divided
- Salt and freshly ground black pepper, to taste
- 1 cup butternut squash, peeled and diced
- ½ cup dried cranberries (or fresh if available)
- ½ cup cooked brown rice or wild rice
- 2 tbsp fresh thyme leaves (or 1 tsp dried thyme)
- 1 clove garlic, minced
- 1 tbsp maple syrup or honey (optional, for a touch of sweetness)
- ¼ cup chopped walnuts or pecans (optional, for added crunch)
How Much Time Will You Need?
This recipe takes about 10 minutes to prep, 35-40 minutes to roast the squash, plus another 10 minutes baking the stuffed squash. In total, plan for about 55-60 minutes from start to finish.
Step-by-Step Instructions:
1. Roast the Butternut Squash Halves:
Preheat your oven to 400°F (200°C). Drizzle 1 tablespoon of olive oil over the halved butternut squash, and season with salt and pepper. Place the squash cut side down on a baking sheet lined with parchment paper. Roast for 35-40 minutes, or until the squash is tender when pierced with a fork.
2. Prepare the Filling:
While the squash is roasting, toss the diced butternut squash with the remaining 1 tablespoon of olive oil, minced garlic, thyme leaves, salt, and pepper in a medium bowl. Heat a skillet over medium heat and lightly toast the diced squash until the edges start to caramelize, about 5-7 minutes. Add dried cranberries and cooked rice to the skillet and warm for 2-3 minutes. Stir in maple syrup or honey if you’d like a touch of sweetness.
3. Stuff and Bake:
Remove the roasted squash halves from the oven and carefully turn them cut side up. Fill each half with the sautéed medley from the skillet. If using, sprinkle chopped walnuts or pecans on top. Return the stuffed squash halves to the oven and bake for another 10 minutes, allowing the flavors to blend and the topping to warm through.
4. Serve Warm:
Take the squash out of the oven and garnish with a few fresh thyme leaves. Serve warm and enjoy this flavorful, colorful dish that’s perfect as a side or a light main!
Can I Use Frozen Butternut Squash for This Recipe?
Yes, you can! Just make sure to thaw it completely and pat it dry before using to avoid excess moisture. You may need to reduce the roasting time slightly since frozen squash can be softer.
Can I Make This Dish Ahead of Time?
Absolutely! Prepare and roast the squash halves and the filling separately, then assemble and bake just before serving. It reheats well in the oven at 350°F for about 10-15 minutes.
What Can I Substitute for Dried Cranberries?
If you don’t have cranberries, dried cherries or raisins make great alternatives. Fresh cranberries can work too but might need a bit of added sweetener to balance their tartness.
How Should I Store Leftovers?
Store leftovers in an airtight container in the refrigerator for up to 3 days. Reheat gently in the oven or microwave until warmed through, adding a sprinkle of water if needed to keep it moist.