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Preheat oven to 400 degrees and place rack in upper third of oven
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Place a sheet of parchment paper on a rimmed cookie sheet
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Place prepared butternut squash and shallots on parchment covered cookie sheet
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Chop 1 chili in adobo sauce finely, whisk 1 tablespoon with olive oil, drizzle over squash
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season somewhat generously with salt and pepper, toss well (if squash isn't completely coated in olive oil you can add a little more)
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place squash in the oven and cook for 40-45 minutes
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While squash cooks, make pico de gallo and guacamole (see recipe links above)
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When squash is almost done cooking, fry tortillas in olive oil or butter until crispy
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To plate: place two tortillas on each plate, top with butternut squash, spoon pico de gallo over the top, add a couple springs of cilantro, sprinkle with a few leaves of arugula, pepitas and cotija cheese, serve