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Heat oven to 180C/160C fan/gas 4. Toss the pumpkin (or squash) in a little oil on a baking tray. Roast until soft enough to squash with the back of a fork – this can take between 40 mins and 1 hr, depending on the type of pumpkin or squash you use. Set aside to cool.
Meanwhile, on a lightly floured work surface, roll out the pastry to the thickness of a £1 coin. Drape it over your rolling pin and lift into a 23cm fluted tart tin. Push the pastry into the corners of the tin using a scrap of excess pastry (you’re less likely to pierce the pastry this way than using a finger). Trim the excess pastry, leaving about 1cm hanging over the edge of the tin; it will shrink as it cooks. Chill for 20 mins.
Increase the oven to 200C/180C fan/gas 6. Line the tart case with a sheet of baking parchment (scrunch it up first to make it more pliable), then fill with baking beans or dry rice. Bake for 15 mins until the sides look golden, then remove the parchment and filling. Bake for another 5-10 mins until the base looks biscuity and dry. Trim the edges with a small, serrated knife.
Tip the roasted pumpkin (or squash), maple syrup, sugar, salt, spices, cornflour and milk into a food processor or blender and blitz until smooth. Pour through a sieve into a small pan and cook for 5 mins, stirring continuously, until thickened.
Fill the tart case with the pumpkin filling, then return to the oven and lower the heat to 180C/160C fan/gas 4. Bake for 30 mins until the filling is set when you wobble the tart tin. Cool for 20-25 mins. Dust with icing sugar and serve warm, or chill and serve within two days.