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Roast your butternut squash until soft, about 25 minutes at 400F
In a blender, pureé your squash until smooth, feel free to add a bit of water to help the process!
Gradually pour in the milk and continue to mash the squash with your spoon. Use an immersion blender to blend the mixture until fully combined. If you do not have an immersion blender, remove the sauce from the heat, let it cool slightly and blend it in a large blender. When it is smooth, pour it back into your skillet.
Keep this sauce on low heat while you cook your pasta, stir occasionally.
Cook the pasta until al dente, about 6-8 minutes, drain and reserve about ½ cup of the pasta water.
Combine the pasta, butternut sauce, and all the cheeses. Gradually add in pasta water as needed, stir until the sauce fully coats the pasta and the cheese is melty.
Top with red pepper flakes if you'd like some heat, and serve warm.