Holiday Wild Rice Stuffed Delicata Squash

This holiday season, I'm excited to be sharing with you one of my absolute favorite dishes to make for a special late fall or winter occasion: these festive, comforting, and nourishing wild rice stuffed delicata squash halves. These can easily act as a main dish for plant-based eaters and a side dish for meat eaters, so they're the perfect addition to any holiday meal.

Everything about this dish is so festive and special because all of the ingredients are such classic winter holiday symbols. Citrus! Pomegranate! Decadent fresh figs! Walnuts! Rosemary! Everything here reminds me of the holiday table at my Italian grandmother's house.

There's something about stuffing a squash that's so symbolic of a special holiday meal. In reality, stuffed squash is pretty easy and hands-off to prepare, but yet it just seems so intricate. This is definitely a meal that you can make all winter long, yet also pull out for a special get-together because it's such a show-stopper.

Are you familiar with delicata squash? It's my secret winter squash weapon! Their long shape and striped skin are really beautiful, but perhaps more importantly they're the easiest, fastest winter squash to cook. The skin is edible, so there's no peeling, and they cook much faster than other types of winter squash. Just scoop out the seeds and roast away!

The other main ingredient here is wild rice, which takes a little while to cook but is completely worth it. You'll toss the wild rice in a flavorful dressing while it's still hot, which is my favorite way of encouraging rice to soak up flavor. Add in dried cranberries for sweetness, crunchy walnuts, and some very festive garnishes and you have yourself a totally holiday-worthy centerpiece.

I'm very happy to be collaborating with Saratoga Olive Oil to bring you this festive winter recipe. This is actually our third recipe together; remember to check out our Grilled Peach and Farro Salad and our Sweet, Salty, and Spicy Watermelon Poblano Salad this summer!

This stuffed squash makes use of two of Saratoga Olive Oil's most decadent, cozy, wintry products: Vermont Maple Balsamic and Rosemary Olive Oil. The combination of the two is utter winter perfection, and the sweetness of the balsamic is the most wonderful complement to the earthiness and herbaceousness of the oil.

Looking to get your hands on these beauties?? Saratoga Olive Oil ships! They have a gorgeous assortment of infused olive oils, dark balsamic vinegars, and white balsamic vinegars, as well as single-origin oils and infused sea salts. I'm very lucky to work about a mile from the store, and I walk down all the time with my empty bottles for refills. If you're local too (Burlington, Vermont!) mention this blog post at the store to save 10%.

Looking to change this recipe up? I've made it with great success using all sorts of other winter squashes (kabocha is my favorite alternative). I highly suggest adding some caramelized onions to the filling if you don't mind an extra step. You can use pecans instead of walnuts, switch up the garnishes, or use brown rice instead of wild rice. If I'm feeling really over the top, I mix in some veggie sausage that I've browned in a skillet. This recipe is really flexible, so do what you love!

If you're planning to serve this at a big holiday meal, you can easily double the recipe. The leftovers are absolutely divine, so don't hesitate to make more than you think you'll need. I've also included suggestions below for how to prep this dish in advance in order to make things more efficient on the day of the big meal.

Isn't special holiday food just the best?? I think dishes like this are so nostalgic and comforting. Having a platter of these stuffed squash halves at your holiday get-together will be such a treat for any plant-based eaters but will also be loved by non-herbivores just as much.

Happy holidays! Hope your Solstice and everything else you celebrate are filled with happiness and love.

Please share your creation so I can see how you've interpreted the concept! Tag "The Rogue Brussel Sprout" on Facebook or hashtag #theroguebrusselsprout on Instagram.

Disclosure: This post is sponsored by Saratoga Olive Oil. However, all opinions and thoughts are my own. Thank you for supporting the brands that keep The Rogue Brussel Sprout running.

Love stuffed squash? What about soup in a squash?!? Check out my Kabocha Squash Soup Bowls, they're so much fun and perfect for cozy winter meals.

Thoughts About Ingredients
(These are all just suggestions, since rogue is more fun than recipe)

For the Dressing
  • 0.25 c Saratoga Olive Oil Vermont Maple Balsamic. Or any other fall-inspired balsamic like their Fig, Cranberry Pear, or Pomegranate. If you can't get your hands on something like that, I'd use 3 tbsp regular balsamic and 1 tbsp maple syrup. If you're in the Burlington Vermont store, remember to mention this blog post in order to save 10%.
  • 2 tbsp Saratoga Olive Oil Rosemary Olive Oil. Or any other fall herby oil like their Herbes de Provence or Tuscan Herb. Otherwise, use any robustly-flavored oil and a palmful of very finely chopped fresh rosemary.
  • 1 tbsp thyme leaf. Fresh is wonderful if you have it, but dry works fine too.
  • Zest of an orange
  • 0.25 tsp sea salt
  • Very generous black pepper
For the Squash
  • 1 c wild rice
  • 0.25 c unsweetened dried cranberries
  • 0.25 c chopped walnuts
  • 2 large or 3 small delicata squashes
  • Handful of pomegranate arils
  • Slices of a couple small citrus fruits, like mandarins or clementines
  • Handful of fresh figs, cut into quarters
  • Generous sprinkle of flaky finishing salt, like fleur de sel

Thoughts About Method
(These are all just suggestions, be creative and make it yours)
  1. Make the dressing and set it aside; I like to let it sit for a little while so that the flavors can meld (hint: double the dressing recipe and use the extra for fall salads!).
  2. Cook the wild rice as directed. Note that it may take as long as an hour if you use a long-grain rice.
  3. While the rice is cooking, prepare the squash. Preheat the oven to 425. Cut the ends off the squash, cut each in half lengthwise, and scoop out the seeds. Bake cut-side down in a well-oiled baking dish for 30-45 minutes, depending on the size of the squash. You want them to be tender throughout but still holding their shape. Make sure not to over-cook them since they'll collapse when you try to stuff them.
  4. When all of the water has evaporated from the rice, leave the heat on low and add in the dressing, cranberries, and walnuts. Give it all a good toss and let it sit on the heat for another few minutes so that the rice absorbs all the flavors of the dressing and the cranberries plump up.
  5. Transfer the squash halves to a serving platter, then fill each squash half with the wild rice stuffing.
  6. When you're ready to serve, garnish with pomegranate arils, citrus slices, and fresh figs. Finish it all off with a sprinkle of sea salt.
  7. Serve any extra stuffing on the side, or make a bed of it underneath the squash halves.
NOTE: If you want to prepare this dish ahead of time, you can easily make the stuffing (rice, dressing, cranberries, and walnuts) and roast the squash a day or two ahead of time. Store them separately for best results. To reheat, a microwave works great and keeps them moist; otherwise, stuff the squashes and put them in a 350 degree oven in a covered baking dish until warmed through. Add the garnishes (pomegranate, citrus slices, figs) just before serving.


  1. This dinner is as pretty as it is delicious. The juicy citrus with savory squash was wonderful. Once the pomegranate is prepared, it’s easy and fast enough for a week night meal. This will be on our repeat list!

    1. The Rogue Brussel SproutDecember 19, 2020 at 6:11 PM

      Oh good, I'm so glad to hear! I love delicata as a "weeknight squash"- it's so fast and easy!


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