Slice the tomatoes into rounds & place in a bowl, adding a sprinkling of sugar to each layer to draw out the liquid. Put aside.
Shell chestnuts by making an "X" incision only in the bottom round portion of each nut.
Place the chestnuts on a baking tray in a small amount of water and bake at 220c for 10 minutes. Let cool enough to handle.
Slip intact nuts from shells, discard shells. Place nuts in a saucepan with milk, vanilla, sugar, cinnamon and nutmeg and let simmer, 10 minutes. Smash chestnuts using a potato masher and let mixture reduce to form a puree.
Preheat oven 220C. Roll out pastry to be 3mm thick, use a rolling pin to transfer to a pie tin or dish. Chill pastry in fridge 30 minutes. Pull together remaining pastry and chill, wrapped in plastic.
Prick pastry base a few times with a fork, cover with baking paper and pie weights, then blind bake in oven 20 minutes. Remove paper and weights, reduce heat to 180C and bake another 25 minutes, until golden brown on base.
Spoon the chestnut mixture into pie base, then top with tomatoes in a circular pattern. Sprinkle with 1/2 tablespoon sugar.
Roll out remaining pastry into a length the same as pie. Make a lattice crust. Sprinkle over remaining sugar. Bake at 180C for 20 minutes. Cool on a wire rack and serve.
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