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Preheat oven to 325F.
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Butter and line with parchment, a 9x5 inch loaf pan.
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In a large bowl, add flour, baking powder, baking soda, cinnamon, nutmeg, and salt, mix with a whisk until combined.
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In a medium bowl, add sugar, olive oil, squash puree, and eggs. Whisk until combined.
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Pour the squash mixture into the dry flour mixture, and whisk until just combined.
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Mix the chocolate into the batter.
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Pour the batter into the loaf pan, and bake 75 to 90 minutes, until browned on top and a toothpick inserted into the center comes out clean (their will likely be some chocolate streaks, but there should be no batter on the toothpick).
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Once baked, remove from oven, and let cool in pan for 20 minutes. Then run a knife along the ends of the cake and use the parchment to remove the cake to cool on a wire rack for at least 20 minutes before icing.
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While the cake is cooling, in a dry pan on medium heat, roast the pepitas about 3-5 minutes until lightly toasted and fragrant.
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To make the icing, whisk together icing sugar and hot water, adding a small amount of additional water as necessary, until it has reached the consistency of honey. Add the olive oil, whisking constantly. Pour the glaze over the cooled cake, allowing it to drip over the sides.
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Sprinkle cocoa nibs and the roasted pepitas on top of the glazed cake.
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Allow the glaze to set 60 minutes before serving.