Roasted Squash Stuffed with Roasted Vegetables

Roasted Squash Stuffed with Roasted Vegetables! This is one of my all time favorite holiday recipes - a rainbow of delicious healthy veggies piled into roasted squash halves. A beautiful, awe-inspiring vegetable side dish that's perfect for Thanksgiving or any festive meal. And all of the chopping, roasting and stuffing can be done ahead of time!

There is a fair bit of chopping and prep work involved here but the result is something very special. If you are looking to bring excitement to the table for a special occasion, roasted squash stuffed with roasted vegetables will do the trick. 

The Roasted Vegetable Stuffing

For the vegetable stuffing, I chose Brussels sprouts, red bell peppers, red onions, kale, and butternut squash. I love the variety of flavors, colors and textures in this mix of veggies.

If you feel like branching out, this recipe is very adaptable to substitutions. Choose your favorite seasonal vegetables or whatever is looking freshest and best at the market. Chunked carrots or sweet potatoes would work really well here. So would roasted broccoli or even oyster mushrooms or shiitakes.

Which winter squash is best for roasting and stuffing?

I tested three different types of winter squash - acorn, carnival and sweet dumpling. They all worked really well for this dish. Select whichever ones look best at the market.

How to make Roasted Squash Stuffed with Roasted Vegetables

This roasted squash recipe is prepared stages: first all the veggies are roasted. Next the roasted veggies are tossed with pomegranate molasses, salt and pepper, and they're piled into the roasted squash halves. Just before serving, the stuffed squash halves are heated in the oven.

How to prepare this dish ahead

You can roast the squash and all the veggies up to a day in advance and keep them in covered containers in the fridge. Assemble the dish an hour or two before your meal. Pop them in the oven to heat them up just before serving.

One important tip: If storing the veggies in the fridge, be sure to let them come to room temperature before reheating, so you don't have to overcook them to get them hot.

What to serve with roasted stuffed squash

Veggie-stuffed roasted squash goes well alongside almost anything that comes out of the oven: roast turkey, roast pork,  roast chicken, broiled salmon, just to name a few. 

Or serve these delicious stuffed roasted squash halves as a vegetarian or vegan main dish. You can finish them with crumbled feta or toasted nuts for a little tasty topping that adds some protein to the mix. 

Other Roasted Vegetable Recipes you might like

• Roasted Sweet Potatoes with Cranberry Maple Citrus Glaze
• Roasted Vegetable Antipasto
• Garlicky Roasted Butternut Squash
• Roasted Tomatoes and Mushrooms with Grilled Bread
• Roasted Cauliflower, Potatoes and Chickpeas with Kalamata Olive Vinaigrette

Here's the Stuffed Roasted Squash Recipe. If you try this recipe, I hope you'll come back to leave a star rating and a comment. I'd love to know what you think!

Roasted Squash Stuffed with Roasted Vegetables

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5 Stars 4 Stars 3 Stars 2 Stars 1 Star

4.5 from 4 reviews

• Author: Lisa
• Total Time: 2 hours
• Yield: 6 1x

Print Recipe

Description

A medley of roasted vegetables served in roasted squash halves. A great side dish for a special occasion.

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Ingredients

Units USM Scale 1x2x3x

For the Squash

• 3 small to medium acorn squash (substitute carnival or sweet dumpling squash)
• 2 tablespoons olive oil
• kosher salt

For The Roasted vegetables

• 2 pounds Brussels sprouts, trimmed (if very large, slice in half)
• 2 red bell peppers, halved, seeds and ribs removed, sliced into bite-sized strips
• 2 small red onions, peeled, root ends cut off, and each cut into 8 wedges, layers separated
• 1 butternut squash (2 ½ - 3 pounds) peeled, halved lengthwise, seeds and strings scooped out, cut into ¾-inch cubes
• 1 bunch curly kale, washed, tough stems removed, torn into bite sized pieces
• Olive oil for brushing vegetables (about ½ cup total)
• Kosher salt for seasoning vegetables
• Fresh ground black pepper
• 4 tablespoons pomegranate molasses - you can find this at specialty food stores, Middle Eastern Grocers, Whole Foods Market, and sometimes at Trader Joe's. If you can't find it, you can substitute 3 ½ tablespoons good quality balsamic vinegar whisked with a teaspoon of honey or maple syrup.

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Instructions

1. Preheat oven to 400ºF. To prepare the acorn squash 'containers', cut each squash in half crosswise and cut a thin slice off each pointy end, if need be, to create a stable base for each half. Scrape out seeds and strings using a spoon. Place squash halves skin side down on a roasting pan. Pour ⅛ of an inch of water in the bottom of the pan to prevent burning. Brush insides and tops of squash generously with olive oil and sprinkle with salt, to taste. Roast for an hour in the middle of the oven, until tender.
2. While the squash are roasting, prepare the rest of the vegetables. You will need a large bowl and two large, rimmed baking sheets. Put Brussels sprouts in the bowl and toss with 1 ½ tablespoons olive oil and ½ teaspoon salt. Spread into a single layer on a roasting pan. Add butternut squash cubes to the bowl with 2 tablespoons olive oil and ½ teaspoon salt and toss to coat. Spread out in a single layer on the other pan. Add onions and peppers to the bowl and toss with 2 tablespoons oil and ½ teaspoon salt. Make some room for onions and peppers at one end of each pan. Put trays in the top and middles shelves of the oven. Roast for 15 minutes. Toss veggies and switch the positions of the trays. Roast for 15 minutes more or until veggies are cooked through - peppers, onions and Brussels will start to brown.
3. Toss the kale leaves in the large bowl with 1 tablespoon of olive oil and a pinch of salt. Put kale onto a roasting pan and cook in the center of the oven for 15-20 minutes until tender and crisp on the edges.
4. At this point, you can store all the roasted veggies and the squash halves in air tight containers in the fridge for a day. Bring to room temperature before continuing.
5. Preheat oven to 350ºF. To assemble the dish, place squash haves skin side down on a roasting pan. Drizzle ½ teaspoon pomegranate molasses over the inside of each squash half. Sprinkle with salt and pepper to taste. Toss all the vegetables gently in a large bowl with 3 tablespoons of pomegranate molasses and salt and pepper, to taste. Mound the roasted vegetables inside each half, allowing the extra veggies to fall onto the tray. Heat for 15-25 minutes, until warmed through. Serve squash with extra veggies mounded on top. Enjoy!

• Prep Time: 1 hour
• Cook Time: 1 hour
• Category: Main Dish or Side Dish
• Method: Roast
• Cuisine: Out Of This World

Originally published November 2013. Updated November 2020 with added nutritional information, some new photos and some clarifying details in the written post. Same delicious recipe!