I was recently asked to fill out a questionnaire about me and my blog.  One of the questions was “What is your most requested dish – your specialty?”  I thought about it for a while – it felt like a really tough question, at first.  I considered the dishes that are popular with my family such as Aleppo pepper chicken, sukiyaki, and chicken parm.  I also thought about choosing one of the special dishes that I cook for the holidays – I make a great brisket and a mean chicken soup with matzo balls.  But I couldn’t get comfortable with calling just one of those dishes my specialty.  Then it hit me that,  without question, my specialty is roasted vegetables.  I make them all the time, they always get oohs and aahs, and it makes me feel extra happy when I cook something that is both super healthy and completely delicious.  This recipe for roasted squash stuffed with roasted fall vegetables is a high impact version of my specialty – a celebration of healthy and delicious.  Serve this as a side dish with roasted meat or chicken, or as a vegetarian main course. It’s also the perfect festive dish for Thanksgiving.



I tested three different types of winter squash – acorn, carnival and sweet dumpling.  They all worked really well for this dish.


For the stuffing, I chose to roast brussels sprouts, red bell peppers, red onion, kale, and cubed butternut squash.  I think you’ll enjoy the combination of flavors, colors and textures. But you can substitute any vegetables that you like – chunked carrots or sweet potatoes would work really well.  So would roasted broccoli or even oyster mushrooms or shiitakes.


Most of the vegetables can roast at the same temperature for the same amount of time – 400 degrees F for about 30 minutes, give or take, depending on your oven.  Just be sure to switch the position of the trays after 15 minutes to insure even cooking.


Kale needs only 15-20 minutes in the oven.  That’s enough time for the leaves to get tender and just a bit crisp on the edges.


After everything is roasted, toss with sweet and tangy pomegranate molasses, assemble on a baking tray, and heat in the oven.  If you want to prepare this ahead, you can roast everything in advance and assemble it the next day and reheat.  Just be sure to let the veggies get to room temperature before reheating, so you don’t have to overcook them to get them warm.


Cheers to healthy and delicious!

Recipe type: Main Dish or Side Dish
Cuisine: Out of this World
Prep time:
Cook time:
Total time:
Serves: 6
A celebration of fall - a medley of roasted fall vegetables served in roasted squash halves, with pomegranate molasses.
  • Squash halves
  • 3 small to medium acorn squash (substitute carnival or sweet dumpling squash)
  • 2 tablespoons olive oil
  • kosher salt
  • Roasted vegetables
  • 2 pounds brussels sprouts, trimmed and washed (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 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 3½ tablespoons good quality balsamic vinegar whisked with a teaspoon of honey or maple syrup.
  1. Preheat oven to 400ºF. Prepare the acorn squash Cut each squash in half lengthwise and cut a thin slice off each pointy end, if need be, to create a stable base. Scrape out seeds and strings using a spoon. Place squash, 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, shallow roasting pans or jellyroll pans. Put brussels sprouts in the bowl and toss with 1½ 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. Assembling the dish Preheat oven to 350ºF. 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!


My favorite local (near Boston, MA) sources for pomegranate molasses:

Sofra Bakery

Formaggio Kitchen


  1. Bess Resnick says

    I have made this recipe twice, the first time with the acorn squash and the second time, without. I also couldn’t find pomegranate molasses in LA so I used the balsamic/maple syrup version. The recipe is perfect, hot or room temperature. It will become a staple of mine. Thanks so much.

  2. Dorinda says

    I made this tonight with my daughter for a main course. Truly delicious! We tossed with balsamic and honey, but would love to try the pomegranate molasses. We added goat cheese to the top … love it!


  1. […] 86. Roasted Squash Stuffed with Roasted Vegetables When you stuff one healthy ingredient with other healthy ingredients you can’t go wrong. Here there’s a squash that’s been stuffed with roasted Brussels sprouts, bell peppers, and more squash. It’s a virtual who’s who of veggies, and you’ll benefit from all of the vitamins, minerals, and fiber. […]

Leave a Reply

Your email address will not be published. Required fields are marked *