Roasted Squash, Wilted Greens & Spiced Shallot Oil

23 November 2025 Dairy Free Gluten Free Vegetarian Friendly
There are a few guarantees in life, one of them being that every November I am going to slide into these pages with a roasted squash/pumpkin concoction on a bed of leaves (probably green) and a sauce that you can use all year around.

And this year I am here, moments before Thanksgiving with this doozie of a recipe.  Yes, it’s a recognisable roasted squash you have seen before on a bed of braised greens, but this year they are dressed with a spiced shallot oil that’s literally to die for.  

You can make the oil in advance.  I like to make extra and keep it in the fridge to use like confit garlic, but if you are short on time you can also make it while the squash roasts and then drizzle all the crispy shallot and chilli bits over the dish when you are ready to serve.  This is a punchy tonic against the sweet turkey and cranberry sauce on the festive table and it makes excellent leftovers. A perfect winter party piece.

Roasted Squash, Wilted Greens & Spiced Shallot Oil

Servings

4-6

servings
Prep time

15

minutes
Cooking time

40

minutes

Feel free to replace the cavolo nero with chard, sprout tops or grilled radicchio. A combo of all of them is also spectacular

Ingredients

  • 1.5kg Kaboocha squash (the orang one) or use crown prince, hokkaido, delicata or acorn work well

  • a good glug (1-2tbsp) of shallot oil if you have made it or olive oil

  • 1 tsp flaky sea salt

  • a few thyme sprigs

  • 500g cavolo nero

  • For the Spiced Shallot Oil
  • 125ml olive oil

  • 1 banana shallot, thinly sliced

  • 2 cloves of garlic, peeled and left whole

  • 1 red chilli, thinly sliced (or 1/2 tsp chilli flakes)

  • 1 cinnamon stick

  • 1 star anise

  • 1 tsp honey

  • 1/2 tsp salt

Directions

  • Preheat your oven to 200C (400F)
  • Start by getting the oil going:
    Place all the ingredients in a small saucepan. Make sure they are fully submerged in the oil (you may need to add a little more if necessary) and simmer very gently for about 20 minutes, occasionally gently stirring so as not to splash the hot oil. Do not rush here – cook this on a low heat to make sure the garlic and shallots brown rather than burn. Have a small sieve and a clean jar on hand as once the oil is finished cooking, immediately strain, separating the oil and the aromatics. Remove the garlic cloves, cinnamon stick and star anise, reserving the golden, crunchy shallot and chilli slices.
  • This allows the oil to cool down without burning them. Once the oil has cooled down you can add them back in ready to use.
  • Meanwhile while the oil is gently bubbling away, roast the squash.
  • To slice your pumpkins with ease, use this hack.
  • Place the slices on a tray or two (depending on their size) lined with baking parchment.
  • Drizzle the wedges with some of the spiced oil if you already have some to hand or with some olive oil and a little Aleppo pepper or allspice. Season well with salt and gently mix everything together so they are all coated in the flavours. Arrange in one layer on the pan(s).
  • Roast in a hot oven for 30 minutes, turning half way thought. If you are using smaller squash they might not need as long on their second side.
  • While the squash is roasting, prep the cavolo nero. Rinse them well and strip the leaves from the main central rib (I pull them from the base of the rib all the way up to the top in one motion). Very Roughly chop the leaves, but o not worry about drying them, the little bit of excess water will help with the cooking process.
  • When the squash is almost ready, heat a medium sized sauté pan. When it’s hot, drizzle in some olive oil or spiced oil if you have some to hand and drop in the cavolo nero leaves and season well with a good pinch of sea salt. Toss the leaves around in the oil and allow them to wilt in the pan. You might want to cover them for a minute or two to speed up the process. They will stay bright green and will be just cooked through in 4-5 minutes. Remove from the heat and place on the base of a large serving plate.
  • To assemble: Once the pumpkin is roasted and caramelised, remove it from the oven and transfer the pumpkin wedges on top of the cavolo nero Drizzle over any remaining pan juices over the dish sprinkle over the crispy shallots and chilli from the spiced oil and spoon over a little extra oil over the squash.

Notes

  • this is also delicious with some salted greek yoghurt on the base of the dish to serve. 
Have you made this dish?

Let me know what you think, share your efforts and any tweaks you made to the recipe on Instagram, don’t forget to tag #BuildingFeasts or email me on info@buildingfeasts.com