My favorite special occasion recipe for fall and winter vegetables: Roasted Squash Stuffed with Roasted Vegetables! A rainbow of delicious healthy veggies piled into roasted squash halves. This is a wonderful dish for Thanksgiving or any festive meal. All of the chopping, roasting and stuffing can be done ahead of time!
These beautiful, bountiful veggie stuffed roasted squash halves are a great side dish for the holidays. They go well with roast turkey, roast pork, roast chicken, broiled salmon…. They also work well as a vegetarian main course.
For the vegetable stuffing I chose Brussels sprouts, red bell peppers, red onions, kale, and butternut squash. I think you’ll enjoy the variety of flavors, colors and textures in this mix.
But 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 TO ROAST?
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 recipe is prepared stages: first roast the squash halves and all the other vegetables. Next stuff the squash halves with vegetables and roast until heated through.
- Roast the Squash Halves: Brush the insides of the squash halves with olive oil, season them with salt and pepper, and roast them in a 400ºF for an hour, until tender.
- Roast the Vegetables: Toss the butternut squash, Brussels sprouts and peppers – with olive oil salt and pepper and arrange them in a single layer on two rimmed baking sheets. Roast them in a 400ºF oven for 30 minutes.
- Roast the Kale: Rub kale with a little olive oil and salt, spread it out on a baking sheet and roast for 15-20 minutes, just enough time for the leaves to get tender and a bit crisp on the edges.
- Assemble The Dish: Toss the roasted vegetables with sweet and tangy pomegranate molasses and pile them into the roasted squash halves. Set the stuffed roasted squash halves on a baking tray, heat them in the oven, done!
PREP THIS AHEAD
If you want to prepare this this ahead, you can roast everything in advance and assemble it the next day and reheat. Be sure to let the veggies get to room temperature before reheating so you don’t have to overcook them to get them hot.
If you like this dish, you’ll love these too: Roasted Sweet Potatoes with Cranberry Maple Citrus Glaze, Roasted Vegetable Antipasto, Garlicky Roasted Butternut Squash, Roasted Tomatoes and Mushrooms with Grilled Bread, Roasted Vegetable Quinoa Salad with Feta, and Roasted Cauliflower, Potatoes and Chickpeas with Kalamata Olive Vinaigrette.
Here’s the recipe for Roasted Squash Stuffed with Roasted Vegetables. 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!Print
Roasted Squash Stuffed with Roasted Vegetables
A celebration of fall – a medley of roasted fall vegetables served in roasted squash halves, with pomegranate molasses. A great side dish for a special occasion.
- Prep Time: 1 hour
- Cook Time: 1 hour
- Total Time: 2 hours
- Yield: 6 1x
- Category: Main Dish or Side Dish
- Method: Roast
- Cuisine: Out of this World
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 (2½ – 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 1/2 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 3½ tablespoons good quality balsamic vinegar whisked with a teaspoon of honey or maple syrup.
- Prepare the acorn squash: Preheat oven to 400ºF. 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 1/8 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.
- Roast The Vegetables: While the squash are roasting prepare the rest of the vegetables. You will need a large bowl and two large, shallow roasting pans or jellyroll pans. 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 1/2 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.
- 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.
- 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.
- Assemble the dish Preheat oven to 350ºF. Place squash haves skin side down on a roasting pan. Drizzle 1/2 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!
Originally published November 2013. Updated October 2018 with added nutritional information, some new photos and some tweaks to the written post.
Keywords: roasted vegetables, Vegetarian holiday side dish, Vegan, roasted vegetable side dish, Thanksgiving side dish
My favorite local (near Boston, MA) sources for pomegranate molasses: