Roasted Chestnut Cranberry Stuffed Squash (Vegan GF)

A tender butternut squash cooked until sticky, stuffed with a chestnut, cranberry and mushroom mix and baked again as a roll. Tie it up with string and serve as the main piece for a plant-based and gluten-free roast dinner.

It’s that time of year where we all want the next best nut roast recipe or the best way to cook all kinds of vegetables. I may have just found my favourite way to cook butternut squash – and I’ve solved my questions of what I fancy with my roast dinners. This Roasted Chestnut Cranberry Stuffed Squash is really impressive but is equally as simple. It takes some time to roast but that’s the hardest part done!

Roasted Chesnut Cranberry Stuffed Squash
Roasted Chesnut Cranberry Stuffed Squash

The filing for this stuffed squash roll has all the wonderful textures, aromas and flavours that you want in a roast dinner – plus it’s naturally vegan and gluten-free. Here’s what goes into the filling:

  • Quinoa or bulgar wheat: or use another grain, something small is best. Cook this until fluffy. Note that bulgar wheat is not gluten-free.
  • Mushrooms: these are quite common in a lot of vegan roast dinner and stuffed vegetable dishes for good reason. Cook them until they release their juices, and the textures is tender.
  • Garlic: for flavour
  • Herbs: I use fresh thyme and fresh rosemary in a lot of my roasted vegetable recipes this time of year and this Roasted Chestnut Cranberry Stuffed Squash is no expectation. They work so beautifully together and have that classic Christmas-Winter smell and flavour. If you don’t have fresh, you could use dried herbs, too.
  • Roasted chestnuts: buy these pre-roasted and usually vacuum packed so you can just chop them up and add them into the mix. If you cannot find roasted chestnuts, you could use another nut like cashews or hazelnuts or if you want to keep this nut-free, use pumpkin or sunflower seeds.
  • Dried cranberries: these are a classic this time of year and I cannot get enough of them when paired with roasted vegetables and nuts. If you aren’t a fan, use raisins or chop up some dried apricots.
  • Tamari soy sauce: this adds such a depth of flavour to the mix so is really important!
Roasted Chesnut Cranberry Stuffed Squash
Roasted Chesnut Cranberry Stuffed Squash

Make up the filling for the Roasted Chestnut Cranberry Stuffed Squash while the squash roasts for the first time. Scoop out the seeds and discard (or roast them for snacks) before scooping out more flesh to make a larger cavity for the filling. Add this squash to the filling and then compact it all into the squash halves. Fold them back as one, tige together with string and bake again for 10 minutes to bring it all together. The smell is amazing!

Once out of the oven, slice the Roasted Chestnut Cranberry Stuffed Squash thickly and serve with your favourite roast dinner accompaniments like sticky glazed parsnips and carrots, potatoes and these Balsamic Roasted Sprouts. These sprouts are the same as I have been making for these, but they finally got an upgrade with some new photos to really show them off. I don’t choose to eat sprouts any other way! Tender, sticky slightly tart but sweet, roast them with sticky red onion until crisp and so flavoursome.

Balsamic Glazed Brussel Sprouts
Balsamic Glazed Brussel Sprouts

I hope you will enjoy this flavour-packed, hearty, wholesome and healthful Roasted Chestnut Cranberry Stuffed Squash – it is perfect for roast dinners and for special occasions, too. It is naturally vegan and gluten-free with nut-free options and makes for a showstopper centrepiece! 

If you are looking for other roast vegetable ideas, how about my:

Roasted Chestnut Cranberry Stuffed Squash (Vegan GF)

  • Servings: 4-6 as a side or 2-3 as a main
  • Difficulty: easy
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A tender butternut squash cooked until sticky, stuffed with a chestnut, cranberry and mushroom mix and baked again as a roll. Tie it up with string and serve as the main piece for a plant-based and gluten-free roast dinner.

Ingredients

    For the Squash:
  • 1 large butternut squash, halved
  • Olive oil
  • Salt and pepper
  • Filling:
  • 100g quinoa or bulgar wheat (or half and half)
  • 100g mushrooms, small dice
  • 3 garlic cloves, crushed
  • 2 sprigs fresh thyme
  • 1 sprig fresh rosemary
  • 100g chestnuts, chopped
  • 50g dried cranberries
  • 1 tbsp tamari
  • Balsamic Spouts:
  • 200g sprouts, trimmed and halved
  • 1 red onion, chopped
  • 1 tbsp olive oil
  • 1 tbsp balsamic vinegar
  • 1 tbsp maple syrup
  • Salt and pepper

Directions

  1. Preheat the oven to 180Fan/200*C and line a baking tray with parchment paper. Add on the squash, cut-side up and rub all over with olive oil, salt and pepper. Roast for 40-50 minutes until tender and the outside is crisp. Take out the oven.
  2. After 30 minutes, prepare the balsamic sprouts: toss everything together and roast on a line baking tray for 30 minutes.
  3. Meanwhile, make the filling. Cook the quinoa/bulgar wheat according to packet instructions and drain. Heat a frying pan with 1 tbsp olive oil and add the mushroom and garlic. Fry for 10 minutes until really soft and all the juices have been released. Add in the fresh thyme, rosemary, chestnuts and dried cranberries.
  4. Scoop out the seeds from the squash and discard them. Scoop out some of the flesh to make a larger cavity but leave a good edge of squash. Mash the flash with a fork and add into the mushroom frying pan with the cooked quinoa/bulgar wheat and tamari soy sauce. Season with salt and pepper. Stuff the filling into both halves of the squash, making it really compact (you may have extras). Place one half on top of the other and secure with string. Roast for 10 more minutes.
  5. Serve the stuffed squash with any leftover filling, the balsamic sprouts and some pomegranate.
Roasted Chesnut Cranberry Stuffed Squash
Roasted Chesnut Cranberry Stuffed Squash

I can’t wait to hear what you think of this festive main or side dish of Roasted Chestnut Cranberry Stuffed Squash so please let me know in the comments below and tag me in your meals, I love seeing them! I’m @nourishing.amy on Instagram and use the hashtag #nourishingamy. I’m also on TwitterFacebook and Pinterest  – please say hello!

With stuffed squash love x

  1. Hey Amy. Looks super and also never tried roasted butternut squash with veggies and bulgar wheat. Definitely would try with raisins to make it nut free. Also love cranberries in sauces but never tried them dry and happy Monday. I am so enjoying your festive recipes on here and your other socials. Can’t wait to cook 👩🏻‍🍳 them over the festive period, definitely will tag you into my bakes using your splendid professional recipes. Saved to my WordPress saved collection and sorry haven’t read your blog in ages, as well as commenting twice on here and your other socials. 😋😍🌱💕💜❤️😊My dog 🐶 Ben says woofs to you, your family, your bro Ben and your cat Jessie. Hope she is ok? Also can I use cous Cous instead of bulgar wheat or is it similar xxxxxx
    Best Wishes Sophsxxxx

  2. […] ingredients are quite similar to that of my Roasted Chestnut Cranberry Stuffed Squash as all of the flavours just worked so well together that I had to make something else with […]

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  4. Laura says:

    You totally need to put out a paperback or hardcover book! I would buy it in a heartbeat!

  5. […] While we are quite used to seeing pre-roasted chestnuts in festive and savoury dishes like Roasted Stuffed Squash and Nut Roast Cups, we don’t associate them as much with year-round sweets and desserts. All that […]

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  7. Lisa Lines says:

    Hi Great recipe! Could you make this ahead do you think? And how would you suggest reheating? Thank you!
    Lisa

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