Add all the squash ingredients into a large baking tray and roast on a medium heat (200°C / 400°F / Gas Mark 6) until soft and a little browned.
Roughly mash the roasted squash with a masher.
For the Pesto
Add all pesto ingredients into a blender or food processor and blend until you have a chunky paste. Add more oil or salt if needed.
For the Mushrooms
Add all the mushrooms & garlic into a large pan with the olive oil.
Gently fry until the mushrooms shrink. Then add the wine & herbs.
Cook until the liquid mostly evaporates.
To Assemble the Pie:
Open out the packet of filo pastry & cut the filo pastry into thin triangles (as pictured). You can cut all the layers together.
Slick the layers of filo pastry with olive oil and oil the tin. If you are using a little ramekin or bowl to create the centre of the wreath, oil that too. It is much easier if you use something to create your centre.
Assemble layers of pastry in the base of the dish: lay the larger end of the triangle on the outside edge, the pointy side facing the 'hole'. The pastry should be long enough to go over the edges of the tin. (This will help form the lid of the pie later)
Keep layering until the whole pan has 2-3 layers of pastry over it. Add extra oil on some layers if they're a bit dry.
Now, fill the 'wreath' with the fillings.
First, smear your kale pesto on the pastry.
Add the mushrooms layer.
Then add your layer of the mashed butternut squash.
Sprinkle over the chestnuts and cranberries.
Finally, carefully close the all the edges of the filo pastry over the filling. You will need to do this bit by bit.
If there are any gaps in the top of the pie, add some strips of extra pastry. You can also add a few more pieces of pastry ruffled up with a little oil for that crucnhy wreath topping!
Finally, brush with extra oil & bake in the oven until crispy and golden. About 20 minutes at around 200°C / 400°F / Gas Mark 6.
To Serve
Remove the outer ring from the wreath & take the ramekin or inner bowl out from the middle.
If the pastry is looking a little soggy, add the wreath back into the oven for 5 minutes or so to crisp up.
Put the whole wreath (bottom of tin and all) onto a pretty plate. Decorate with rosemary sprigs and serve as part of a festive meal!
Video
Notes
🌶️Substitutions & Variations
Here are some easy ways you can switch up this recipe:
Different pastry- instead of filo pastry, use puff or shortcrust pastry.
Gluten-Free- use a gluten-free pastry to replace the filo pastry. Gluten free pastry can be a little tough so be gentle when handling it.
Different pie filling- swap out one or any of the layers for a different type of pesto, some roasted sweet potatoes or other root vegetables. Choose festive flavours such as celeriac or parsnip or why not add in wild mushroom or creamy vegan chk'n as a filling.